Synthesis of symmetrical biaryl compounds by homocoupling reaction

Tetrahedron

Volumn 75, Issue 13, 2019, Pages 1865-1959

  Vasconcelos, Stanley N S ^a   Reis, Joel S ^a   de Oliveira, Isadora M ^a   Balfour, Michael N ^a   Stefani, Hélio A ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYST; CONFORMATION; ORGANIC CHEMISTRY; REVIEW;

EID: 85061566142     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2019.02.001     Document Type: Review

References (233)

1. de Meijere, A., Stang, P.J., (eds.) Metal-catalyzed Cross-Coupling Reactions, second ed., 2004, Wiley-VCH, Weinheim.
2. Beller, M., Bolm, C., (eds.) Transition Metals for Organic Synthesis, second ed., 2004, Wiley-VCH, Weinheim.
3. Marion, N., Nolan, S.P., Well-defined N-heterocyclic carbenes−palladium(II) precatalysts for cross-coupling reactions. Acc. Chem. Res. 41 (2008), 1440–1449.
4. Ma, D., Cai, Q., Copper/amino acid catalyzed cross-couplings of aryl and vinyl halides with nucleophiles. Acc. Chem. Res. 41 (2008), 1450–1460.
5. Denmark, S.E., Regens, C.S., Palladium-catalyzed cross-coupling reactions of organosilanols and their salts: practical alternatives to boron- and tin-based methods. Acc. Chem. Res. 41 (2008), 1486–1499.
6. Sherry, B.D., Fürstner, A., The promise and challenge of iron-catalyzed cross-coupling. Acc. Chem. Res. 41 (2008), 1500–1511.
7. 3 as ligands. Acc. Chem. Res. 41 (2008), 1555–1564.
8. Roglans, A., Pla-Quintana, A., Moreno-Maas, M., Diazonium salts as substrates in palladium-catalyzed cross-coupling reactions. Chem. Rev. 106 (2006), 4622–4643.
9. Hassan, J., Sevignon, M., Gozzi, C., Schulz, E., Lemaire, M., Aryl−aryl bond formation one century after the discovery of the ullmann reaction. Chem. Rev. 102 (2002), 1359–1470.
10. Ullmann, F., Bielecki, J., Ueber synthesen in der biphenylreihe. Chem. Ber. 34 (1901), 2174–2185.
11. Smith, G.B., Dezeny, G.C., Hughes, D.L., King, A.O., Verhoeven, T.R., Mechanistic studies of the Suzuki cross-coupling reaction. J. Org. Chem. 59 (1994), 8151–8156.
12. Birkenhager, W.H., de Leeuw, P.W., Non-peptide angiotensin type 1 receptor antagonists in the treatment of hypertension. J. Hypertens. 17 (1999), 873–881.
13. Goa, K.L., Wagstaff, A.J., Losartan potassium: a review of its pharmacology, clinical efficacy and tolerability in the management of hypertension. Drugs 51 (1996), 820–845.
14. Solladie, G., Gottarelli, G., Liquid crystals and chirality: application to the determination of absolute configurations and to the conformational analysis of biaryls. Tetrahedron 43 (1987), 1425–1437.
15. Gray, G.W., Molecular Structures and the Properties of Liquid Crystals. 1962, Academic Press, London.
16. Anton, U., Goltner, C., Mullen, K., Reductive transformations, 20. Synthesis of n-alkyl-substituted perylenes and terrylenes via alkali-metal induced cyclization of oligonaphthylenes. Chem. Ber. 125 (1992), 2325–2330.
17. Bringmann, G., Gunther, C., Ochse, M., Schupp, O., Tasler, S., Herz, W., Falk, H., Kirby, G.W., Moore, R.E., (eds.) Progress in the Chemistry of Organic Natural Products, vol. 82, 2001, Springer, New York, 1–293.
18. Nicolaou, K.C., Boddy, C.N.C., Brase, S., Winssinger, N., Chemistry, biology, and medicine of the glycopeptide antibiotics. Angew. Chem. Int. Ed. 38 (1999), 2096–2152.
19. Kumar, P., Pathak, P.K., Gupta, V.K., Srivastava, B.K., Kushwaha, B.S., Flurbiprofen and its derivatives of many therapeutic uses-a recent report. Asian J. Chem. 16 (2004), 558–562.
20. Gasparani, L., Ongini, E., Wenk, G., Non-steroidal anti-inflammatory drugs (NSAIDs) in Alzheimer's disease: old and new mechanisms of action. J. Neurochem. 91 (2004), 521–536.
21. Fanta, P.E., The Ullmann synthesis of biaryls, 1945-1963. Chem. Rev. 64 (1964), 613–632.
22. Dermer, O.C., Edmison, M.T., Radical substitution in aromatic nuclei. Chem. Rev. 57 (1957), 77–122.
23. McKillop, A., Turrell, A.G., Young, D.W., Taylor, E.C., Thallium in organic synthesis. 58. Regiospecific intermolecular oxidative dehydrodimerization of aromatic compounds to biaryls using thallium(III) trifluoroacetate. J. Am. Chem. Soc. 102 (1980), 6504–6512.
24. For a review seeSainsbury, M., Modern methods of aryl-aryl bond formation. Tetrahedron 36 (1980), 3327–3359.
25. Ryabov, A.D., Deiko, S.A., Yatsimirsky, A.K., Berezin, I.V., Palladium(II)-catalyzed oxidation of substituted benzenes to biaryls by tris(trifluoroacetato)thallium(III). Tetrahedron Lett. 22 (1981), 3793–3796.
26. For a review see,Kozhenvikov, I.V., Matveev, K.I., Usp. Khim. (Russ.) 47 (1978), 1231–01260.
27. Lourak, M., Vanderesse, R., Fort, Y., Caubere, P., Activation of reducing agents. Sodium hydride containing complex reducing agents. 31. Nickel containing complex NiCRAL's as very efficient agents in promoting homocoupling of aryl halides. J. Org. Chem. 54 (1989), 4840–4844.
28. 4 NI. An efficient method for the synthesis of biaryls and bipyridines. Bull. Chem. Soc. Jpn. 63 (1990), 80–87.
29. Unger, M.O., Fouty, R.A., Oxidative coupling of toluene through organometallic intermediates. J. Org. Chem. 34 (1968), 18–21.
30. Barton, D.H.R., Ozbalik, N., Ramesh, M., The chemistry of organobismuth reagents: Part XIII ligand coupling induced by Pd(0). Tetrahedron 44 (1988), 5661–5668.
31. Yamashita, J., Inoue, Y., Kondo, T., Hashimoto, H., Ullmann-type coupling reaction of aryl trifluoromethanesulfonates catalyzed by in situ-generated low valent nickel complex. Chem. Lett., 1986, 407–408.
32. Jutand, A., Mosleh, A., Palladium and nickel catalyzed synthesis of biaryls from aryl triflates in the presence of zinc powder. Synlett 8 (1993), 568–570.
33. Miura, M., Hashimoto, H., Itoh, K., Nomura, M., Palladium-catalyzed desulfonylative homocoupling of arylsulfonyl chlorides in the presence of titanium(IV) isopropoxide. Chem. Lett., 1990, 459–460.
34. Gilman, H., Lichtenwalter, M., Relative reactivities of organometallic compounds. XXV. Coupling reaction with halides of group VIII metals. J. Am. Chem. Soc. 61 (1939), 957–959.
35. Kharasch, M.S., Fields, E.K., Factors determining the course and mechanisms of Grignard reactions. IV. The effect of metallic halides on the reaction of aryl grignard reagents and organic halides. J. Am. Chem. Soc. 63 (1941), 2316–2320.
36. Stefani, H.A., Guarezemini, A.S., Cella, R., Homocoupling reactions of alkynes, alkenes and alkyl compounds. Tetrahedron 66 (2010), 7871–7918.
37. Chen, J.-S., Krogh-Jespersen, K., Khinast, J.G., Base- and ligand-free heterogeneously catalyzed homocoupling of arylboronic acids. J. Mol. Catal. Chem. 285 (2008), 14–19.
38. 2 -catalyzed room temperature homocoupling reaction of arylboronic acids under air without ligand. Catal. Commun. 9 (2008), 97–100.
39. Smith, K.A., Campi, E.M., Jackson, W.R., Marcuccio, S., Naeslund, C.G.M., Deacon, G.B., High yields of symmetrical biaryls from palladium catalysed homocoupling of arylboronic acids under mild conditions. Synlett 1 (1997), 131–132.
40. Punna, S., Díaz, D.D., Finn, M.G., Palladium-catalyzed homocoupling of arylboronic acids and esters using fluoride in aqueous solvents. Synlett 13 (2004), 2351–2354.
41. 2 -catalyzed homocoupling of arylboronic acids in water and ionic liquid. J. Mol. Catal. Chem. 273 (2007), 240–243.
42. Koza, D.J., Carita, E., An efficient high yielding approach for the homocoupling of aryl boronic acids. Synthesis 15 (2002), 2183–2186.
43. Adamo, C., Amatore, C., Ciofini, I., Jutand, A., Lakmini, H., Mechanism of the palladium-catalyzed homocoupling of arylboronic acids: key involvement of a palladium peroxo complex. J. Am. Chem. Soc. 128 (2006), 6829–6836.
44. Yadav, J.S., Gayathri, K.U., Ather, H., Rehman, H., Prasad, A.R., Utility of semicarbazones as ligands in newly made palladium complex for facile Suzuki homocoupling reaction of alkyl and aryl boronic acids. J. Mol. Catal. Chem. 271 (2007), 25–27.
45. Celedón, C.A.C., Medina, J.A.R., Rayo, D.M., García, L.C., Oxidative homocoupling of arylboronic acids catalyzed by a 4-aminoantipyrine–Pd(II) complex. Appl. Organomet. Chem. 29 (2015), 439–442.
46. Mu, B., Li, T., Fu, Z., Wu, Y., Cyclopalladated ferrocenylimines catalyzed-homocoupling reaction of arylboronic acids in aqueous solvents at room temperature under ambient atmosphere. Catal. Commun. 10 (2009), 1497–1501.
47. Yamamoto, Y., Homocoupling of arylboronic acids with a catalyst system consisting of a palladium(II) N-heterocyclic carbene complex and p-benzoquinone. Synlett 12 (2007), 1913–1916.
48. Jin, Z., Guo, S.-X., Gu, X.-P., Qiu, L.-L., Song, H.-B., Fang, J.-X., Highly active, well-defined (cyclopentadiene)(N-heterocyclic carbene)palladium chloride complexes for room temperature Suzuki–Miyaura and Buchwald–Hartwig cross-coupling reactions of aryl chlorides and deboronation homocoupling of arylboronic acids. Adv. Synth. Catal. 351 (2009), 1575–1585.
49. Yoshida, H., Yamaryo, Y., Ohshita, J., Kunai, A., Base-free oxidative homocoupling of arylboronic esters. Tetrahedron Lett. 44 (2003), 1541–1544.
50. Wong, M.S., Zhang, X.L., Ligand promoted palladium-catalyzed homocoupling of arylboronic acids. Tetrahedron Lett. 42 (2001), 4087–4089.
51. Moreno-Mañas, M., Pérez, M., Pleixats, R., Palladium-catalyzed Suzuki-type self-coupling of arylboronic acids. A mechanistic study. J. Org. Chem. 61 (1996), 2346–2351.
52. Hashim, J., Glasnov, T.N., Kresmsnes, J.M., Kappe, C.O., Symmetrical bisquinolones via metal-catalyzed cross-coupling and homocoupling reactions. J. Org. Chem. 71 (2006), 1707–1710.
53. Cravotto, G., Beggiato, M., Penoni, A., Plamisano, G., Tollari, S., Léveque, J.-M., Bonrath, W., High-intensity ultrasound and microwave, alone or combined, promote Pd/C-catalyzed aryl–aryl couplings. Tetrahedron Lett. 46 (2005), 2267–2271.
54. Cravotto, G., Palmisano, G., Tollari, S., Nano, G.M., Penoni, A., The Suzuki homocoupling reaction under high-intensity ultrasound. Sonochemistry 12 (2005), 91–94.
55. Luque, R., Baruwati, B., Varma, R.S., Magnetically separable nanoferrite-anchored glutathione: aqueous homocoupling of arylboronic acids under microwave irradiation. Green Chem. 12 (2010), 1540–1543.
56. Zhou, L., Xu, Q.X., Jiang, H.F., Palladium-catalyzed homocoupling of boronic acids with supported reagents in supercritical carbon dioxide. Chin. Chem. Lett. 18 (2007), 1043–1046.
57. Prastaro, A., Ceci, P., Chiancone, E., Boffi, A., Fabrizi, G., Cacchi, S., Homocoupling of arylboronic acids and potassium aryltrifluoroborates catalyzed by protein-stabilized palladium nanoparticles under air in water. Tetrahedron Lett. 51 (2010), 2550–2552.
58. Mitsudo, K., Shiraga, T., Tanaka, H., Electrooxidative homocoupling of arylboronic acids catalyzed by electrogenerated cationic palladium catalysts. Tetrahedron Lett. 49 (2008), 6593–6595.
59. Mitsudo, K., Shiraga, T., Kagen, D., Shi, D., Becker, J.Y., Tanaka, H., Pd/TEMPO-catalyzed electrooxidative synthesis of biaryls from arylboronic acids or arylboronic esters. Tetrahedron 65 (2009), 8384–8388.
60. 2 /p-Benzoquinone-catalyzed anaerobic electrooxidative homocoupling of arylboronic acids, arylboronates and aryltrifluoroborates in DMF and/or water. Eur. J. Org. Chem. 27 (2008), 4567–4570.
61. Yamamoto, Y., Suzuki, R., Hattori, K., Nishiyama, H., Base- and phosphine-free palladium-catalyzed homocoupling of arylboronic acid derivatives under air. Synlett 7 (2006), 1027–1030.
62. Carretin, S., Guzman, J., Corma, A., Supported gold catalyzes the homocoupling of phenylboronic acid with high conversion and selectivity. Angew. Chem. Int. Ed. 44 (2005), 2242–2245.
63. González-Arellano, C., Corma, A., Iglesias, M., Sánches, F., Homogeneous and heterogenized Au(III) Schiff base-complexes as selective and general catalysts for self-coupling of aryl boronic acids. Chem. Commun., 2005, 1990–1992.
64. Corma, A., González-Arellano, C., Iglesias, M., Pérez-Ferreras, S., Sánchez, F., Heterogenized gold(I), gold(III), and palladium(II) complexes for C-C bond reactions. Synlett 11 (2007), 1771–1774.
65. Gonzalez-Arellano, C., Adad, A., Corma, A., Garcia, H., Iglesias, M., Sanchez, F., Catalysis by gold(I) and gold(III): a parallelism between homo- and heterogeneous catalysts for copper-free sonogashira cross-coupling reactions. Angew. Chem. Int. Ed. 46 (2007), 1536–1538.
66. Corma, A., Gonzalez-Arellano, C., Iglesias, M., Sanchez, F., Gold nanoparticles and gold(III) complexes as general and selective hydrosilylation catalysts. Angew. Chem. Int. Ed. 46 (2007), 7820–7822.
67. Gonzalez-Arellano, C., Corma, A., Iglesias, M., Sanchez, F., Soluble gold and palladium complexes heterogenized on MCM-41 are effective and versatile catalysts. Eur. J. Inorg. Chem. 7 (2008), 1107–1115.
68. Matsuda, T., Asai, T., Shiose, S., Kato, K., Homocoupling of arylboronic acids catalyzed by simple gold salts. Tetrahedron Lett. 52 (2011), 4779–4781.
69. Cheng, G., Luo, M., Homocoupling of arylboronic acids catalyzed by CuCl in air at room temperature. Eur. J. Org. Chem. 13 (2011), 2519–2523.
70. Kirai, N., Yamamoto, Y., Homocoupling of arylboronic acids catalyzed by 1,10-phenanthroline-ligated copper complexes in air. Eur. J. Org. Chem. 12 (2009), 1864–1867.
71. 4 -Mediated homocoupling of arylboronic acids under ligand- and base-free conditions in air. Synthesis 1 (2011), 91–96.
72. Vogler, T., Studer, A., Rhodium-catalyzed oxidative homocoupling of boronic acids. Adv. Synth. Catal. 350 (2008), 1963–1967.
73. Mao, J., Hua, Q., Xie, G., Yao, Z., Shi, D., Iodine-promoted efficient homocoupling of arylboronic acids in PEG-400 under aerobic conditions. Eur. J. Org. Chem. 14 (2009), 2262–2266.
74. Sakurai, H., Tsunoyama, H., Tsukuda, T., Oxidative homocoupling of potassium aryltrifluoroborates catalyzed by gold nanocluster under aerobic conditions. J. Organomet. Chem. 692 (2007), 368–374.
75. Santos-Filho, E.F., Sousa, J.C., Bezerra, N.M.M., Menezes, P.H., Oliveira, R.A., Environmentally friendly homocoupling reaction of functionalized potassium aryl trifluoroborates salts in aqueous media. Tetrahedron Lett. 52 (2011), 5288–5291.
76. Takashi, N., Hayashi, T., Iron-catalyzed oxidative homocoupling of aryl Grignard reagents. Org. Lett. 7 (2005), 491–493.
77. 2 as the oxidant. Tetrahedron Lett. 49 (2008), 610–613.
78. Zhou, Z., Xue, W., Manganese-catalyzed oxidative homocoupling of aryl Grignard chlorides. J. Organomet. Chem. 694 (2009), 599–603.
79. Cahiez, G., Moyeux, A., Buendia, J., Duplais, C., Manganese- or iron-catalyzed homocoupling of Grignard reagents using atmospheric oxygen as an oxidant. J. Am. Chem. Soc. 129 (2007), 13788–13789.
80. Moglie, Y., Mascaro, E., Nador, F., Vitale, C., Radivoy, G., Nanosized iron- or copper-catalyzed homocoupling of aryl, heteroaryl, benzyl, and alkenyl Grignard reagents. Synth. Commun. 38 (2008), 3861–3874.
81. Chen, S.-Y., Zhagn, J., Li, Y.-H., Wen, J., Bian, S.-Q., Yu, X.-Q., Cobalt-catalyzed homocoupling of aryl and alkenyl bromide using atmospheric oxygen as oxidant. Tetrahedron Lett. 50 (2009), 6795–6797.
82. Mayer, M., Czaplik, W.M., von Wangelin, A.J., Thieme journal awardees – where are they now? On cobalt-catalyzed biaryl coupling reactions. Synlett 18 (2009), 2919–2923.
83. Tang, J., Tang, Y., Yang, J., Zhang, Y., Selenium-promoted homocoupling of grignard reagents. Chin. J. Org. Chem. 33 (2013), 1010–1014.
84. Maji, M.S., Pfeifer, T., Studer, A., Oxidative homocoupling of aryl, alkenyl, and alkynyl Grignard reagents with TEMPO and dioxygen. Angew. Chem. Int. Ed. 47 (2008), 9547–9550.
85. Knochel, P., Dohle, W., Gommermann, N., Kneisel, F.F., Kopp, F., Korn, T., Sapountzis, I., Vu, V.A., Highly functionalized organomagnesium reagents prepared through halogen–metal exchange. Angew. Chem. Int. Ed. 42 (2003), 4302–4320.
86. Ren, H., Krasovskiy, A., Knochel, P., Stereoselective preparation of functionalized acyclic alkenylmagnesium reagents using i-PrMgCl·LiCl. Org. Lett. 6 (2004), 4215–4217.
87. Muraka, S., Möbus, J., Erker, G., Mück-Lichtenfeld, C., Studer, A., TEMPO-mediated homocoupling of aryl Grignard reagents: mechanistic studies. Org. Biomol. Chem. 13 (2015), 2762–2767.
88. Shukla, R., Rathore, R., Octahydro[1,4:5,8]dimethanoanthraquinone as a cheap and readily available electron-transfer oxidant for biaryl synthesis from organocuprates. Synthesis 23 (2008), 3769–3774.
89. Semmelhack, M.F., Helquist, P., Lones, L.D., Keller, L., Mendelson, L., Ryono, L.S., Smith, J.G., Stauffer, R.D., Reaction of aryl and vinyl halides with zerovalent nickel - preparative aspects and the synthesis of alnusone. J. Am. Chem. Soc. 103 (1981), 6460–6471.
90. Haworth, R.D., Lamberton, A.H., Some derivatives of catechol and pyrogallol. Part II. J. Chem. Soc., 1946, 1003–1005.
91. Fliedner, L.J.J.R., Myers, M.J., Schor, J.M., Pachter, I.J., Synthesis and evaluation of 1,ω-diaryl-1,ω-alkanediamines related to the fibrinolytic bis(tetrahydroisoquinolines) and bis(benzylamines). J. Med. Chem. 19 (1976), 202–208.
92. Franke, R., Schnakenburg, G., Waldvogel, S.R., Synthesis of highly fluorinated 2,2′-biphenols and 2,2′-bisanisoles. Org. Lett. 12 (2010), 4288–4291.
93. Waldvogel, S.R., Wehming, K.M., Ramsden, C.A., (eds.) Science of Synthesis, vol. 31, 2007, Thieme, Stuttgart, 235.
94. Waldvogel, S.R., Ramsden, C.A., Thomas, E.J., (eds.) Science of Synthesis Knowledge Updates, vol. 1, 2010, Thieme, Stuttgart, 487.
95. Wu, Q., Wang, L., Immobilization of copper(II) in organic-inorganic hybrid materials: a highly efficient and reusable catalyst for the classic Ullmann reaction. Synthesis 13 (2008), 2007–2012.
96. 2 ] in the presence of metallic zinc and copper. Catal. Lett. 141 (2011), 467–473.
97. Goswami, S., Adak, A.K., Mukherjee, R., Jana, S., Dey, S., Gallagher, J., A convenient palladium catalyzed synthesis of symmetric biaryls, biheterocycles and biaryl chiral diamides. Tetrahedron 61 (2005), 4289–4295.
98. Goswami, S., Jana, S., Fun, H.-K., Recognition of dicarboxylic acids by 3,3′-bipyridine amide based receptors and its supramolecular behavior in solid state. CrystEngComm 10 (2008), 507–517.
99. Luo, F.-T., Jeevanandam, A., Basu, M.K., Efficient and high turnover homocoupling reaction of aryl iodide by the use of palladacycle catalyst. A convenient way to prepare poly-p-phenylene. Tetrahedron Lett. 39 (1998), 7939–7942.
100. Hennings, D.D., Iwana, T., Rawal, V.H., Palladium-catalyzed (Ullmann-type) homocoupling of aryl halides: a convenient and general synthesis of symmetrical biaryls via inter- and intramolecular coupling reactions. Org. Lett. 1 (1999), 1205–1208 and references cited therein.
101. Hassan, J., Gozzi, C., Lemaire, M., Palladium-catalyzed symmetrical and unsymmetrical coupling of aryl halides. C. R. Acad. Sci. Paris, Série IIc, Chimie Chem. 3 (2000), 517–521.
102. Hassan, J., Lavenot, L., Gozzi, C., Lemaire, M., A convenient catalytic route to symmetrical functionalized bithiophenes. Tetrahedron Lett. 40 (1999), 857–858.
103. Hassan, J., Penalva, V., Lavenot, L., Gozzi, C., Lemaire, M., Catalytic alternative of the Ullmann reaction. Tetrahedron 54 (1998), 13793–13804.
104. Penalva, V., Hassan, J., Lavenot, L., Gozzi, C., Lemaire, M., Direct homocoupling of aryl halides catalyzed by palladium. Tetrahedron Lett. 39 (1998), 2559–2560.
105. Brink, G.-J., Arends, I.W.C.E., Sheldon, R.A., Catalytic conversions in water. Part 21: mechanistic investigations on the palladium-catalyzed aerobic oxidation of alcohols in water. Adv. Synth. Catal. 344 (2002), 355–369.
106. Shao, L., Du, Y., Zeng, M., Li, X., Shen, W., Zuo, S., Lu, Y., Zhang, X.-M., Qi, C., Ethanol-promoted reductive homocoupling reactions of aryl halides catalyzed by palladium on carbon (Pd/C). Appl. Organomet. Chem. 24 (2010), 421–425.
107. Qi, C., Sun, X., Lu, C., Yang, J., Du, Y., Wu, H., Zhang, X.-M., Palladium catalyzed reductive homocoupling reactions of aromatic halides in dimethyl sulfoxide (DMSO) solution. J. Organomet. Chem. 694 (2009), 2912–2916.
108. Yu, M., Tang, R.-Y., Li, J.-H., Synthesis of 6,7-dihydro-5H-dibenzo[c,e]azepines and biaryls by palladium-catalyzed Ullmann reaction. Tetrahedron 65 (2009), 3409–3416.
109. Bhattacharjya, A., Klumphu, P., Lipshutz, B.H., Kumada-Grignard-type biaryl couplings on water. Nat. Commun., 6, 2015, 7401.
110. Qi, C., Sun, X., Lu, C., Yang, J., Du, Y., Wu, H., Zhang, X.-M., Palladium catalyzed reductive homocoupling reactions of aromatic halides in dimethyl sulfoxide (DMSO) solution. J. Organomet. Chem. 694 (2009), 2912–2916.
111. Shoji, T., Miyashita, K., Araki, T., Tanaka, M., Maruyama, A., Sekiguchi, R., Ito, S., Okujima, T., Synthesis of 1,2′-biazulenes by palladium-catalyzed unusual homocoupling reaction of 1-haloazulenes in the presence of ferrocene. Synthesis 48 (2016), 2438–2448.
112. Dzhevakov, P., Topchiy, M.A., Zharkova, D.A., Morozov, O.S., Asachenko, A.F., Nechaev, M.S., Miyaura borylation and one-pot two-step homocoupling of aryl chlorides and bromides under solvent-free conditions. Adv. Synth. Catal. 358 (2016), 977–983.
113. Ma, N., Duan, Z., Wu, Y., DAB-Cy as an inexpensive and effective ligand for palladium-catalyzed homocoupling reaction of aryl halides. J. Organomet. Chem. 691 (2006), 5697–5700.
114. Kuroboshi, M., Waki, Y., Tanaka, H., Palladium-catalyzed tetrakis(dimethylamino) ethylene-promoted reductive coupling of aryl halides. J. Org. Chem. 68 (2003), 3938–3942.
115. Ram, R.N., Singh, V., Palladium(II) chloride/EDTA-catalyzed biaryl homocoupling of aryl halides in aqueous medium in the presence of ascorbic acid. Tetrahedron Lett. 47 (2006), 7625–7628.
116. Chang, Y.M., Lee, S.H., Cho, M.Y., Yoo, B.W., Rhee, H.J., Lee, S.H., Yoon, C.M., Homocoupling of aryl iodides and bromides using a palladium/indium bimetallic system. Synth. Commun. 35 (2005), 1851–1857.
117. 2 using indium. Tetrahedron Lett. 49 (2008), 4302–4305.
118. Venkatraman, S., Huang, T., Li, C.-J., Carbon-carbon bond formation via palladium-catalyzed reductive coupling of aryl halides in air and water. Adv. Synth. Catal. 344 (2002), 399–405.
119. Mukhopadhyay, S., Rothenberg, G., Gitis, D., Sasson, Y., On the mechanism of palladium-catalyzed coupling of haloaryls to biaryls in water with zinc. Org. Lett. 2 (2000), 211–214.
120. Mukhopadhyay, S., Rothenberg, G., Sasson, Y., Tuning the selectivity of heterogeneous catalysts: a trimetallic approach to reductive coupling of chloroarenes in water. Adv. Synth. Catal. 343 (2001), 274–278.
121. 2 as a selective agent in palladium-catalyzed reductive Ullmann coupling with zinc in water. J. Org. Chem. 68 (2003), 9867–9869.
122. Abiraj, K., Srinivasa, G.R., Gowda, D.C., Facile synthesis of symmetrical functionalized biaryls from aryl halides catalyzed by commercial zinc dust using ammonium formate. Tetrahedron Lett. 45 (2004), 2081–2084.
123. Abiraj, K., Srinivasa, G.R., Gowda, D.C., Novel and efficient synthesis of symmetrical functionalized biaryls using zinc and triethylammonium formate. Synlett 5 (2004), 877–879.
124. Cravotto, G., Beggiato, M., Penoni, A., Palmisano, G., Tollari, S., Lévêque, J.-M., Bonrath, W., High-intensity ultrasound and microwave, alone or combined, promote Pd/C-catalyzed aryl–aryl couplings. Tetrahedron Lett. 46 (2005), 2267–2271.
125. Hossain, K.M., Shibata, T., Takagi, K., A New synthetic method to biaryls from arylzinc iodides using N-chlorosuccinimide and a catalytic amount of palladium. Synlett 8 (2000), 1137–1138.
126. Hossain, K.M., Kameyama, T., Shibata, T., Takagi, K., Palladium-catalyzed synthesis of biaryls from arylzinc compounds using N-chlorosuccinimide or oxygen as an oxidant. Bull. Chem. Soc. Jpn. 74 (2001), 2415–2420.
127. Qafisheh, N., Mukhopadhyay, S., Sasson, Y., Highly selective Pd-catalyzed reductive coupling of substituted haloarenes with supported phase-transfer catalyst using Zn as the reducing agent. Adv. Synth. Catal. 344 (2002), 1079–1083.
128. Albanese, D., Landini, D., Penso, M., Petricci, S., Homocoupling of aryl halides promoted by tetrabutylammonium fluoride. Synlett 2 (1999), 199–200.
129. Moon, J., Nam, H., Ju, J., Jeong, M., Lee, S., Homocoupling of aryl halides using catalytic system of palladium and phosphite. Chem. Lett. 36 (2007), 1432–1433.
130. 6 as an efficient and highly active catalyst under microwave irradiation. Appl. Organomet. Chem. 29 (2015), 147–151.
131. Tsuji, J., Palladium Reagents and Catalysts. second ed., 2004, Wiley, New York (Chapter 2).
132. Peterson, K.P., Larock, R.C., Palladium-catalyzed oxidation of primary and secondary allylic and benzylic alcohols. J. Org. Chem. 63 (1998), 3185–3189.
133. Stahl, S.S., Palladium oxidase catalysis: selective oxidation of organic chemicals by direct dioxygen-coupled turnover. Angew. Chem. Int. Ed. 43 (2004), 3400–3420.
134. 2 /DMSO-catalyzed aerobic alcohol oxidation: mass-transfer-limitation effects and catalyst decomposition Pathways. J. Am. Chem. Soc. 128 (2006), 4348–4355.
135. Backvall, J.-E., Modern Oxidation Methods. second ed., 2004, Wiley-VCH, Weinheim (Chapter 5).
136. Zeng, M., Du, Y., Shao, L., Qi, C., Zhang, X.-M., Palladium-catalyzed reductive homocoupling of aromatic halides and oxidation of alcohols. J. Org. Chem. 75 (2010), 2556–2563.
137. Huang, Y., Liu, L., Feng, W., Facile palladium–catalyzed homocoupling of aryl halides using 1,4-butanediol as solvent, reductant and O,O-ligand. ChemistrySelect 3 (2016), 630–634.
138. Park, B.R., Kim, K.H., Kim, T.H., Kim, J.N., Palladium-catalyzed benzoin-mediated redox process leading to biaryls from aryl halides. Tetrahedron Lett. 52 (2011), 4405–4407.
139. 2 and agarose hydrogel as a bioorganic ligand, support and reductant. J. Mol. Catal. Chem. 348 (2011), 94–99.
140. Hajipour, A.R., Karami, K., Tavakoli, G., A comparative homocoupling reaction of aryl halides using monomeric orthopalladated complex of 4-methoxybenzoylmethylenetriphenylphosphorane under conventional and microwave irradiation conditions. Appl. Organomet. Chem. 25 (2011), 567–576.
141. Hajipour, A.R., Rafiee, F., Palladium-catalyzed synthesis of symmetrical biaryls under microwave irradiation and conventional heating. Synth. Commun. 43 (2013), 1314–1327.
142. He, H.S., Zhang, C., Ng, C.K.-W., Toy, P.H., Polystyrene-supported triphenylarsines: useful ligands in palladium-catalyzed aryl halide homocoupling reactions and a catalyst for alkene epoxidation using hydrogen peroxide. Tetrahedron 61 (2005), 12053–12057.
143. Toy, P.H., Janda, K.D., New supports for solid-phase organic synthesis: development of polystyrene resins containing tetrahydrofuran derived cross-linkers. Tetrahedron Lett. 40 (1999), 6329–6332.
144. Garibay, P., Toy, P.H., Hoeg-Jensen, T., Janda, K.D., Application of a new solid-phase resin: benzamide ortho-lithiation and the synthesis of a phthalide library. Synlett, 1999, 1438–1440.
145. Wang, L., Zhang, Y., Liu, L., Wang, Y., Palladium-catalyzed homocoupling and cross-coupling reactions of aryl halides in poly(ethylene glycol). J. Org. Chem. 71 (2006), 1284–1287.
146. 2 ) as Pd ligand and solvent for selective dehalogenation or homocoupling of aryl halides. J. Organomet. Chem. 693 (2008), 2469–2472.
147. Caló V., Nacci, A., Monopoli, A., Cotugno, P., Palladium-nanoparticle-catalyzed Ullmann reactions in ionic liquids with aldehydes as the reductants: scope and mechanism. Chem. Eur. J. 15 (2009), 1272–1279.
148. Park, S.B., Alper, H., Convenient palladium-catalyzed homocoupling of iodoarenes in an ionic liquid. Tetrahedron Lett. 45 (2004), 5515–5517.
149. Monopoli, A., Caló V., Ciminale, F., Cotugno, P., Angelici, C., Cioffi, N., Nacci, A., Glucose as a clean and renewable reductant in the Pd-nanoparticle-catalyzed reductive homocoupling of bromo- and chloroarenes in water. J. Org. Chem. 75 (2010), 3908–3911.
150. Mukhopadhyay, S., Yaghmur, A., Baidossi, M., Kundu, B., Sasson, Y., Highly chemoselective heterogeneous Pd-catalyzed biaryl synthesis from haloarenes: reaction in an oil-in-water microemulsion. Org. Process. Res. Dev. 7 (2003), 641–643.
151. Mukhopadhyay, S., Joshi, A.V., Peleg, L., Sasson, Y., Heterogeneous Rh/C-catalyzed direct reductive coupling of haloaryls to biaryls in water. Org. Process. Res. Dev. 7 (2003), 44–46.
152. Karimi, B., Behzadnia, H., Vali, H., Palladium on ionic liquid derived nanofibrillated mesoporous carbon: a recyclable catalyst for the Ullmann homocoupling reactions of aryl halides in water. ChemCatChem 6 (2014), 745–748.
153. Yuan, Y., Bian, Y., Efficient homocoupling reactions of halide compounds catalyzed by manganese(II) chloride. Appl. Organomet. Chem. 22 (2008), 15–18.
154. Moncomble, A., Floch, P.L., Gosmini, C., Cobalt-catalyzed formation of symmetrical biaryls and its mechanism. Chem. Eur. J. 15 (2009), 4770–4774.
155. Kazmierski, I., Gosmini, C., Paris, J.-M., Périchon, J., New progress in the cobalt-catalysed synthesis of aromatic organozinc compounds by reduction of aromatic halides by zinc dust. Tetrahedron Lett. 44 (2003), 6417–6420.
156. Bourne-Branchu, Y., Moncomble, A., Corpet, M., Danoun, G., Gosmini, C., Cobalt-catalyzed oxidative homocoupling of arylzinc species. Synthesis 48 (2016), 3352–3356.
157. Xie, Y., Xu, D., Sun, W.-W., Zhang, S.-J., Dong, X.-P., Liu, B., Zhou, Y., Wu, B., Cobalt-catalyzed oxidative dimerization of 2-phenylpyridine derivatives. Asian J. Org. Chem. 5 (2016), 961–965.
158. Karimi, B., Esfahani, F.K., Unexpected golden Ullmann reaction catalyzed by Au nanoparticles supported on periodic mesoporous organosilica (PMO). Chem. Commun. 47 (2011), 10452–10454.
159. Layek, K., Maheswaran, H., Kantam, L., Ullmann coupling of aryl iodides catalyzed by gold nanoparticles stabilized on nanocrystalline magnesium oxide. Catal. Sci. Technol. 3 (2013), 1147–1150.
160. Yao, W., Gong, W.-J., Li, H.-X., Li, F.-L., Gaoa, J., Lang, J.-P., Synthesis of DMF-protected Au NPs with different size distributions and their catalytic performance in the Ullmann homocoupling of aryl iodides. Dalton Trans. 43 (2014), 15752–15759.
161. Wu, X., Tan, L., Chen, D., Meng, X., Tang, F., Icosahedral gold–platinum alloy nanocrystals in hollow silica: a highly active and stable catalyst for Ullmann reactions. Chem. Commun. 50 (2014), 539–541.
162. Ranu, B.C., Dutta, P., Sarkar, A., Indium promoted reductive homocoupling of alkyl and aryl halides. Tetrahedron Lett. 39 (1998), 9557–9558.
163. Lu, D., Zhang, Y.-Y., Li, J.-H., One-pot, nickel triflate-catalysed homocoupling of aryl chlorides in the presence of metallic magnesium. J. Chem. Res., 2009, 397–399.
164. 2 ). J. Organomet. Chem. 264 (1984), 263–271.
165. Lourak, M., Vanderesse, R., Fort, Y., Caubere, P., Activation of reducing agents. Sodium hydride containing complex reducing agents. 31. Nickel containing complex NiCRAL's as very efficient agents in promoting homocoupling of aryl halides. J. Org. Chem. 54 (1989), 4840–4844.
166. Patti, A., Pedotti, S., Preparation of a chiral ferrocenyl derivative containing a biphenyl unit via nickel-mediated homocoupling. Chirality 17 (2005), 233–236.
167. 2 /Mn-Mediated homocoupling of aryl halides accomplished in the presence of bipyridyl-type ligand. Synlett 10 (2000), 1491–1493.
168. Hayoz, P., Zelewsky, A., New versatile optically active bipyridines as building blocks for helicating and caging ligands. Tetrahedron Lett. 33 (1992), 5165–5168.
169. Yurino, T., Ueda, Y., Shimizu, Y., Tanaka, S., Nishiyama, H., Tsurugi, H., Sato, K., Mashima, K., Salt-free reduction of nonprecious transition-metal compounds: generation of amorphous ni nanoparticles for catalytic c–c bond formation. Angew. Chem. Int. Ed. 54 (2015), 14437–14441.
170. 4 Ni. An efficient method for the synthesis of biaryls and bipyridines. Bull. Chem. Soc. Jpn. 63 (1990), 80–87.
171. Valaeva, V.N., Asachenko, A.F., Kulyabin, P.S., Flid, V.R., Voskoboinikov, A.Z., New catalyst for homocoupling of aryl halides based on nickel complexes with diazabutadiene ligands. Russ. J. Org. Chem. 47 (2011), 1774–1776.
172. 2 /bpy/Mg system in DMF. Appl. Organomet. Chem. 28 (2014), 598–604.
173. Peng, J., Liu, X., Kishi, Y., Catalytic homocoupling of aryl, alkenyl, and alkynyl halides with Ni(II)-complexes and zirconocene dichloride. Tetrahedron Lett. 52 (2011), 2172–2175.
174. Massicot, F., Schneider, R., Fort, Y., Illy-Cherrey, S., Tillement, O., An efficient route to biaryls from aryl halides catalysed by subnanometrical 2,2′-bipyridine liganded Ni–Al clusters. Tetrahedron 57 (2001), 531–536.
175. Raynal, F., Barhdadi, R., Périchon, J., Savall, A., Troupel, M., Water as solvent for nickel-2,2′-bipyridine-catalysed electrosynthesis of biaryls from haloaryls. Adv. Synth. Catal. 344 (2002), 45–49.
176. Chaussard, J., Folest, J.C., Nédélec, J.Y., Périchon, J., Sibille, S., Troupel, M., Use of sacrificial anodes in electrochemical functionalization of organic halides. Synthesis 5 (1990), 369–381.
177. Xu, X., Cheng, D., Pei, W., Iron-catalyzed homocoupling of bromide compounds. J. Org. Chem. 71 (2006), 6637–6639.
178. Bonnemann, H., Bogdanović B., Brinkmann, R., Spliethoff, B., He, D.W., The preparation of finely divided metal powders and transition metal complexes using “organically solvated” magnesium. J. Organomet. Chem. 451 (1993), 23–31.
179. Bogdanovic, B., Schwickardi, M., Transition metal catalyzed preparation of Grignard compounds. Angew Chem. Int. 39 (2000), 4610–4612.
180. Zhang, Y.-Y., Lin, J.-D., Xu, X.-L., Li, J.-H., Triflic salt–catalyzed coupling: iron triflate–catalyzed homocoupling of aryl bromides in the presence of metallic magnesium. Synth. Commun. 40 (2010), 2556–2563.
181. 3 promoted homocoupling. Beilstein J. Org. Chem. 7 (2011), 1064–1069.
182. 5 in the reaction of bis(pentafluorophenyl)palladium(II) complexes with protic acids. Dalton Trans., 2008, 3949–3952.
183. Iyoda, M., Copper-mediated aryl-aryl couplings for the construction of oligophenylenes and related heteroaromatics. Adv. Synth. Catal. 351 (2009), 984–998.
184. RN 1 reactions. J. Org. Chem. 70 (2005), 9063–9066.
185. Farina, V., Krishnan, B., Marshall, D.R., Roth, G.P., Palladium-catalyzed coupling of arylstannanes with organic sulfonates: a comprehensive study. J. Org. Chem. 58 (1993), 5434–5444.
186. Shirakawa, E., Murota, Y., Nakao, Y., Hiyama, T., Homocoupling of organostannanes catalyzed by iminophosphine-palladium. Synlett 10 (1997), 1143–1144.
187. Kang, S.-K., Baik, T.-G., Jiao, X.H., Lee, Y.-T., Copper and manganese-catalyzed homocoupling of organostannanes in the presence of iodine. Tetrahedron Lett. 40 (1999), 2383–2384.
188. Robinson, M.K., Kochurina, V.S., Hanna, J.M. Jr., Palladium-catalyzed homocoupling of arenediazonium salts: an operationally simple synthesis of symmetrical biaryls. Tetrahedron Lett. 48 (2007), 7687–7690.
189. Singh, F.V., Stefani, H.A., Ultrasound-assisted synthesis of symmetrical biaryls by palladium-catalyzed homocoupling of aryl n-butyl tellurides. Synlett 20 (2008), 3221–3225.
190. Hirabayashi, K., Takeda, Y., Shimizu, T., Kamigata, N., Synthesis of cyclic and heterocyclic compounds via gold-catalyzed reactions. Synlett 14 (2005), 2230–2232.
191. Singh, F.V., Stefani, H.A., Ultrasound-assisted synthesis of symmetrical biaryls by palladium-catalyzed detelluration of 1,2-diarylditellanes. Tetrahedron Lett. 51 (2010), 863–867.
192. Jhaveri, S.B., Carter, K.R., Nickel-catalyzed coupling of aryl bromides in the presence of alkyllithium reagents. Chem. Eur. J. 14 (2008), 6845–6848.
193. Jhaveri, S.B., Peterson, J.J., Carter, K.R., Organolithium-activated nickel (OLAN) catalysis: a new synthetic route for polyarylates. Macromolecules 41 (2008), 8977–8979.
194. Alonso, F., Riente, P., Yus, M., Homocoupling of aryl iodides promoted by nickel(0) nanoparticles. Arkivok iv (2008), 8–15.
195. Massicot, F., Schneider, R., Fort, Y., Lithium hydride mediated nickel(0) catalyzed biaryl synthesis from aryl chlorides and bromides. J. Chem. Res. (S), 1999, 664–665.
196. Toummini, D., Ouazzani, F., Taillefer, M., Iron-catalyzed homocoupling of aryl halides and derivatives in the presence of alkyllithiums. Org. Lett. 15 (2013), 4690–4693.
197. Lipshutz, B.H., Wilhelm, R.S., Floyd, D.M., Chemistry of higher order, mixed organocuprates. 1. Substitution reactions at unactivated secondary center. J. Am. Chem. Soc. 103 (1981), 7672–7674.
198. Miyake, Y., Wu, M.W., Rahman, M.J., Kuwatani, Y., Iyoda, M., Efficient construction of biaryls and macrocyclic cyclophanes via electron-transfer oxidation of Lipshutz cuprates. J. Org. Chem. 71 (2006), 6110–6117.
199. Demir, A.S., Reis, O., Emrullahoglu, M., Role of copper species in the oxidative dimerization of arylboronic acids: synthesis of symmetrical biaryls. J. Org. Chem. 68 (2003), 10130–10134.
200. Corey, E.J., Boaz, N.W., Evidence for a reversible d,π*-complexation, β-cupration sequence in the conjugate addition reaction of Gilman reagents with α,β-enones. Tetrahedron Lett. 26 (1985), 6015–6018.
201. Vellekoop, A.S., Smith, R.A.J., The mechanism of organocuprate 1,4-addition reactions with complexes with lithium dimethylcuprate. J. Am. Chem. Soc. 116 (1994), 2902–2913.
202. For electron-transfer oxidation of organometallics, see
203. Cheng, J.-W., Luo, F.-T., Coupling of aryl Grignard reagents by electron transfer to 2,3-dichloropropene. Tetrahedron Lett. 29 (1988), 1293–1294.
204. Chen, C., Xi, C., Lai, C., Wang, R., Hong, X., Coupling reactions of 1,4-dicuprio-1,3-dienes: formation of carbocycles. Eur. J. Org. Chem., 2004, 647–650.
205. Yamaguchi, S., Ohno, S., Tamao, K., Pd(II)-catalyzed oxidative homocoupling of aryl-metal compounds using acrylate dibromide derivatives as effective oxidants. Synlett 10 (1997), 1199–1201.
206. Kang, S.-K., Kim, T.-H., Pyun, S.-J., Copper(I)-catalyzed homocoupling of organosilicon compounds: synthesis of biaryls, dienes and diynes. J. Chem. Soc. Perkin Trans 1 (1997), 797–798.
207. Yoshida, H., Yamaryo, Y., Ohshita, J., Kunai, A., Activator-free oxidative homocoupling of organosilanes catalysed by a palladium–dppp complex. Chem. Commun., 2003, 1510–1511.
208. Jutand, A., Mosleh, A., Nickel- and palladium-catalyzed homocoupling of aryl triflates. Scope, limitation, and mechanistic aspects. J. Org. Chem. 62 (1997), 261–274.
209. Brimble, M.A., Gibson, J.S., Sejberg, J.J.P., Sperry, J., A facile enantioselective synthesis of the dimeric pyranonaphthoquinone core of the cardinalins. Synlett 6 (2008), 867–870.
210. Sperry, J., Gibson, J.S., Sejberg, J.J.P., Brimble, M.A., Enantioselective synthesis of the dimeric pyranonaphthoquinone core of the cardinalins using a late-stage homocoupling strategy. Org. Biomol. Chem. 6 (2008), 4261–4270.
211. Miura, M., Hashimoto, H., Itoh, K., Nomura, M., Palladium-catalyzed desulfonylative homocoupling of arylsulfonyl chlorides in the presence of titanium(IV) isopropoxide. Chem. Lett., 1990, 459–460.
212. Percec, V., Bae, J.-Y., Zhao, M., Hill, D.H., Aryl mesylates in metal-catalyzed homocoupling and cross-coupling reactions. 1. Functional symmetrical biaryls from phenols via nickel-catalyzed homocoupling of their mesylates. J. Org. Chem. 60 (1995), 176–185.
213. Kashiwabara, T., Tanaka, M., Pd-catalyzed desulfonylative homocoupling of arenesulfonyl chlorides in the presence of hexamethyldisilane forming biaryls. Tetrahedron Lett. 46 (2005), 7125–7128.
214. Yang, L., Zeng, T., Shuai, Q., Guo, X., Li, C.-J., Phosphine ligand triggered oxidative decarbonylative homocoupling of aromatic aldehydes: selectively generating biaryls and diarylketones. Chem. Commun. 47 (2011), 2161–2163.
215. Ackermann, L., Novák, P., Vicente, R., Pirovano, V., Potukuchi, H.K., Ruthenium-catalyzed C–H bond functionalizations of 1,2,3-triazol-4-yl-substituted arenes: dehydrogenative couplings versus direct arylations. Synthesis 13 (2010), 2245–2253.
216. Li, Z., Wang, Y., Huang, Y., Tang, C., Xu, J., Wu, X., Efficient palladium(II)-catalyzed homocoupling of thiazole-4-carboxylic or oxazole-4-carboxylic derivatives. Tetrahedron 67 (2011), 5550–5555.
217. Hull, K.L., Lanni, E.L., Sanford, M.S., Highly regioselective catalytic oxidative coupling reactions: synthetic and mechanistic investigations. J. Am. Chem. Soc. 128 (2006), 14047–14049.
218. Chen, X., Dobereiner, G., Hao, X.-S., Giri, R., Maugel, N., Yu, J.-Q., Cu(II)-mediated oxidative dimerization of 2-phenylpyridine derivatives. Tetrahedron 65 (2009), 3085–3089.
219. Iranpoor, N., Shekarriz, M., Homocoupling of substituted benzenes to symmetrical biaryls with mercury(II) in the presence of cerium(IV). J. Chem. Res. (S), 1999, 442–443.
220. Pintori, D.G., Greaney, M.F., Oxidative C-H homodimerization of phenylacetamides. Org. Lett. 13 (2011), 5713–5715.
221. Sun, Y., Man, X., Guo, M., Wang, D., Dong, X., Pan, Y., Zhang, Z., Chiral biphosphine ligands for the Ru-catalyzed enantioselective hydrogenation of β-ketoesters. Tetrahedron Asymmetry 15 (2004), 2185–2188.
222. Masui, K., Ikegami, H., Mori, A., Palladium-catalyzed C-H homocoupling of thiophenes: facile construction of bithiophene structure. J. Am. Chem. Soc. 126 (2004), 5074–5075.
223. Shiraishi, K., Rajca, A., Pink, M., Rajca, S., π-Conjugated conjoined double helicene via a sequence of three oxidative CC- and NN-homocouplings. J. Am. Chem. Soc. 127 (2005), 9312–9313.
224. 3 /KF. Org. Lett. 7 (2005), 5083–5085.
225. Guo, X., Deng, G., Li, C.-J., Ruthenium-catalyzed oxidative homocoupling of 2-arylpyridines. Adv. Synth. Catal. 351 (2009), 2071–2074.
226. Do, H.-Q., Daugulis, O., An aromatic Glaser-Hay reaction. J. Am. Chem. Soc. 131 (2009), 17052–17053.
227. Matsuda, S., Takahashi, M., Monguchi, D., Mori, A., C–H and C–Si functionalization of furan derivatives: palladium-catalyzed homocoupling and arylation reactions. Synlett 12 (2009), 1941–1944.
228. Truong, T., Alvarado, J., Tran, L.D., Daugulis, O., Nickel, manganese, cobalt, and iron-catalyzed deprotonative arene dimerization. Org. Lett. 12 (2010), 1200–1203.
229. Liang, Z., Zhao, J., Zhang, Y., Palladium-catalyzed regioselective oxidative coupling of indoles and One-Pot synthesis of acetoxylated biindolyls. J. Org. Chem. 75 (2010), 170–177.
230. Monguchi, D., Yamamura, A., Fujiwara, T., Somete, T., Mori, A., Oxidative dimerization of azoles via copper(II)/silver(I)-catalyzed CH homocoupling. Tetrahedron Lett. 51 (2010), 850–852.
231. Morimoto, K., Nakae, T., Yamaoka, N., Dohi, T., Kita, Y., Metal-free oxidative coupling reactions via σ-iodonium intermediates: the efficient synthesis of bithiophenes using hypervalent iodine reagents. Eur. J. Org. Chem. 31 (2011), 6326–6334.
232. 2 Mn. Synlett 26 (2015), 1515–1519.
233. Neelamegan, R., Palatnik, M., Frase-Rini, J., Slifstein, M., Abi-Darghan, A., Easwaramoorthy, B., Dimerization of phenols and naphthols using an aqueous sodium hypochlorite. Tetrahedron Lett. 51 (2010), 2497–2499.