Aryl-aryl crosss-couplings that avoid the preparation of haloaromatics

Current Opinion in Drug Discovery and Development

Volumn 11, Issue 6, 2008, Pages 853-869

  Norberg, A M ^a   Sanchez, L ^a   Maleczka Jr , Robert E ^a  

^a MICHIGAN STATE UNIVERSITY   (United States)

Author keywords

Arenes; C H activation; Catalysis; Cross couplings; Haloaromatics; Heteroarenes; Ortho metallation

Indexed keywords

AMINE; CYANIDE; POLYCYCLIC AROMATIC HYDROCARBON; SULFIDE; TOLUENESULFONIC ACID DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID;

CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; REVIEW; SUZUKI REACTION;

CATALYSIS; CHEMISTRY, PHARMACEUTICAL; DRUG DISCOVERY; HALOGENS; PHARMACEUTICAL PREPARATIONS;

EID: 54549124627     PISSN: 13676733     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (122)

1. de Meijere A, Diederich F (Eds): Metal-Catalyzed Cross-Coupling Reactions. Wiley-VCH Verlag GmbH & Co KGaA, Weinheim, Germany (2004).
2. Miyaura N, Suzuki A: Palladium-catalyzed cross-coupling reactions of organoboron compounds. Chem Rev (1995) 95(7):2457-2483.
3. Carey JS, Laffan D, Thomson C, Williams MT: Analysis of the reactions used for the preparation of drug candidate molecules. Org Biomol Chem (2006) 4(12):2337-2347.
4. Chen GS, Bunce NJ: Interaction between halogenated aromatic compounds in the Ah receptor signal transduction pathway. Environ Toxicol (2004) 19(5):480-489.
5. Scott WJ, McMurry JE: Olefin synthesis via organometallic coupling reactions of enol triflates. Acc Chem Res (1988) 21(2):47-54.
6. Rottländer M, Knochel P: Palladium-catalyzed cross-coupling reactions with aryl nonaflates: A practical alternative to aryl triflates. J Org Chem (1998) 63(1):203-208.
7. 2H). J Org Chem (2008) 73(2):711-714.
8. Marion N, Navarro O, Mei J, Stevens ED, Scott NM, Nolan SP: Modified (NHC)Pd(allyl)Cl (NHC = N-heterocyclic carbene) complexes for room-temperature Suzuki-Miyaura and Buchwald-Hartwig reactions. J Am Chem Soc (2006) 128(12):4101-4111.
9. Molander GA, Ellis N: Organotrifluoroborates: Protected boronic acids that expand the versatility of the Suzuki coupling reaction. Acc Chem Res (2007) 40(4):275-286.
10. Darses S, Genet J-P: Potassium trifluoro(organo)borates: New perspectives in organic chemistry. Eur J Org Chem (2003) (22):4313-4327.
11. Leadbeater NE: Fast, easy, clean chemistry by using water as a solvent and microwave heating: The Suzuki coupling as an illustration. Chem Commun (2005) (23):2881-2902.
12. Kabalka GW, Zhou L-L, Naravane A: Microwave enhanced ligand- and base-free cross-coupling of potassium aryltrifluoroborates salts with aryl triflates. Tetrahedron Lett (2006) 47(38):6887-6889.
13. Molander GA, Biolatto B: Efficient ligandless palladium-catalyzed Suzuki reactions of potassium aryltrifluoroborates. Org Lett (2002) 4(11):1867-1870.
14. Su W, Urgaonkar S, McLaughlin PA, Verkade JG: Highly active palladium catalysts supported by bulky proazaphosphatrane ligands for Stille cross-coupling: Coupling of aryl and vinyl chlorides, room temperature coupling of aryl bromides, coupling of aryl triflates, and synthesis of sterically hindered biaryls. J Am Chem Soc (2004) 126(50):16433-16439.
15. Handy CJ, Manoso AS, McElroy WT, Seganish WM, DeShong P: Recent advances in siloxane-based aryl-aryl coupling reactions: Focus on heteroaromatic systems. Tetrahedron (2005) 61(52):12201-12225.
16. Riggleman S, DeShong P: Application of silicon-based cross-coupling technology to triflates. J Org Chem (2003) 68(21):8106-8109.
17. Satoh T, Miura M: Catalytic direct arylation of heteroaromatic compounds. Chem Lett (2007) 36(2):200-205.
18. Roger J, Doucet H: Aryl triflates: Useful coupling partners for the direct arylation of heteroaryl derivatives via Pd-catalyzed C-H activation-functionalization. Org Biomol Chem (2008) 6(1):169-174.
19. Alonso F, Beletskaya IP, Yus M: Non-conventional methodologies for transition-metal catalysed carbon-carbon coupling: A critical overview. Part 2: The Suzuki reaction. Tetrahedron (2008) 64(14):3047-3101.
20. Nguyen HN, Huang X, Buchwald SL: The first general palladium catalyst for the Suzuki-Miyaura and carbonyl enolate coupling of aryl arenesulfonates. J Am Chem Soc (2003) 125(39):11818-11819.
21. Zhang L, Meng T, Wu J: Palladium-catalyzed Suzuki-Miyaura cross-couplings of aryl tosylates with potassium aryltrifluoroborates. J Org Chem (2007) 72(24):9346-9349.
22. Ackermann L, Althammer A, Born R: Catalytic arylation reactions by C-H bond activation with aryl tosylates. Angew Chem Int Ed (2006) 45(16):2619-2622.
23. Ackermann L, Vicente R, Althammer A: Assisted ruthenium-catalyzed C-H bond activation: Carboxylic acids as cocatalysts for generally applicable direct arylations in apolar solvents. Org Lett (2008) 10(11):2299- 2302.
24. 2(dppe)- catalyzed cross-coupling of aryl mesylates, arenesulfonates, and halides with arylboronic acids. J Org Chem (2004) 69(10):3447-3452.
25. Wenkert E, Michelotti EL, Swindell CS: Nickel-induced conversion of carbon-oxygen into carbon-carbon bonds. One-step transformations of enol ethers into olefins and aryl ethers into biaryls. J Am Chem Soc (1979) 101(8):2246-2247.
26. Wenkert E, Michelotti EL, Swindell CS, Tingoli M: Transformation of carbon-oxygen into carbon-carbon bonds mediated by low-valent nickel species. J Org Chem (1984) 49(25):4894-4899.
27. Kakiuchi F, Usui M, Ueno S, Chatani N, Murai S: Ruthenium-catalyzed functionalization of aryl carbon-oxygen bonds in aromatic ethers with organoboron compounds. J Am Chem Soc (2004) 126(9):2706-2707.
28. Tobisu M, Shimasaki T, Chatani N: Nickel-catalyzed cross-coupling of aryl methyl ethers with aryl boronic esters. Angew Chem Int Ed (2008) 47(26):4866-4869.
29. Liebeskind LS, Srogl J: Heteroaromatic thioether-boronic acid cross-coupling under neutral reaction conditions. Org Lett (2002) 4(6):979-981.
30. Alphonse F-A, Suzenet F, Keromnes A, Lebret B, Guillaumet G: Palladium-catalyzed 3-thiomethyltriazine-boronic acid cross coupling: Easy access to 3-substituted-1,2,4-triazines. Synlett (2002) (3):447-450.
31. Miller JA: C-C bond activation with selective functionalization: Preparation of unsymmetrical biaryls from benzonitriles. Tetrahedron Lett (2001) 42(40):6991-6993.
32. Miller JA, Dankwardt JW, Penney JM: Nickel catalyzed cross-coupling and amination reactions of aryl nitriles. Synthesis (2003) (11):1643-1648.
33. Miller JA, Dankwardt JW: Nickel catalyzed cross-coupling of modified alkyl and alkenyl Grignard reagents with aryl- and heteroaryl nitriles: Activation of the C-CN bond. Tetrahedron Lett (2003) 44(9):1907-1910.
34. Penney JM, Miller JA: Alkynylation of benzonitriles via nickel catalyzed C-C bond activation. Tetrahedron Lett (2004) 45(25):4989-4992.
35. Tobisu M, Chatani N: Catalytic reactions involving the cleavage of carbon-cyano and carbon-carbon triple bonds. Chem Soc Rev (2008) 37(2):300-307.
36. Sengupta S, Sadhukhan SK: Iodoarenediazonium salts: A new class of aromatic substrates for differential palladium catalyzed reactions. Tetrahedron Lett (1998) 39(7):715-718.
37. Roglans A, Pla-Quintana A, Moreno-Mañas M: Diazonium salts as substrates in palladium-catalyzed cross-coupling reactions. Chem Rev (2006) 106(11):4622-4643.
38. 2-symmetric thiourea and its application in the Pd-catalyzed cross-coupling reactions with arenediazonium salts under aerobic conditions. Org Lett (2004) 6(2):221-224.
39. Saeki T, Son E-C, Tamao K: Boron trifluoride induced palladium-catalyzed cross-coupling reaction of 1-aryltriazenes with areneboronic acids. Org Lett (2004) 6(4):617-619.
40. Blakey SB, MacMillan DWC: The first Suzuki cross-couplings of aryltrimethylammonium salts. J Am Chem Soc (2003) 125(20):6046-6047. • Describes a novel, mild method to activate anilines for metal-catalyzed cross-coupling reactions.
41. 3SiO). J Am Chem Soc (1996) 118(21):5132-5133.
42. Ueno S, Chatani N, Kakiuchi F: Ruthenium-catalyzed carbon-carbon bond formation via the cleavage of an unreactive aryl carbon-nitrogen bond in aniline derivatives with organoboronates. J Am Chem Soc (2007) 129(19):6098-6099.
43. Kakiuchi F, Kan S, Igi K, Chatani N, Murai S: A ruthenium-catalyzed reaction of aromatic ketones with arylboronates: A new method for the arylation of aromatic compounds via C-H bond cleavage. J Am Chem Soc (2003) 125(7):1698-1699. • Describes a directed C-H activation that is compatible with the cross-coupling of arylboronates, and so complements related C-H activation strategies.
44. Alberico D, Scott ME, Lautens M: Aryl-aryl bond formation by transition-metal-catalyzed direct arylation. Chem Rev (2007) 107(1):174-238.
45. Kawai H, Kobayashi Y, Oi S, Inoue Y: Direct C-H bond arylation of arenes with aryltin reagents catalysed by palladium complexes. Chem Commun (2008) (12):1464-1466.
46. Seregin IV, Gevorgyan V: Direct transition metal-catalyzed functionalization of heteroaromatic compounds. Chem Soc Rev (2007) 36(7):1173-1193.
47. Yang S-D, Sun C-L, Fang Z, Li B-J, Li Y-Z, Shi Z-J: Palladium- catalyzed direct arylation of (hetero)arenes with aryl boronic acids. Angew Chem Int Ed (2008) 47(8):1473-1476.
48. Campeau L-C, Stuart DR, Fagnou K: Recent advances in intermolecular direct arylation reactions. Aldrichimica Acta (2007) 40(2):35-41.
49. 3 C-H bonds in simple carboxylic acids. J Am Chem Soc (2007) 129(12):3510-3511.
50. Vogler T, Studer A: Oxidative coupling of arylboronic acids with arenes via Rh-catalyzed direct C-H arylation. Org Lett (2008) 10(1):129-131.
51. Li B-J, Yang S-D, Shi Z-J: Recent advances in direct arylation via palladium-catalyzed aromatic C-H activation. Synlett (2008) (7):949-957.
52. Shi Z, Li B, Wan X, Cheng J, Fang Z, Cao B, Qin C, Wang Y: Suzuki-Miyaura coupling reaction by Pd(II)-catalyzed aromatic C-H bond activation directed by an N-alkyl acetamino group. Angew Chem Int Ed (2007) 46(29):5554-5558.
53. Yang S, Li B, Wan X, Shi Z: Ortho arylation of acetanilides via Pd(II)-catalyzed C-H functionalization. J Am Chem Soc (2007) 129(19):6066-6067.
54. Snieckus V: Directed ortho-metalation. Tertiary amide and O-carbamate directors in synthetic strategies for polysubstituted aromatics. Chem Rev (1990) 90(6):879-933.
55. Nguyen TH, Chau NT, Castanet AS, Nguyen KP, Mortier J: First general, direct, and regioselective synthesis of substituted methoxybenzoic acids by ortho metalation. J Org Chem (2007) 72(9):3419- 3429.
56. Alessi M, Larkin AL, Ogilvie KA, Green LA, Lai S, Lopez S, Snieckus V: Directed ortho metalation-boronation and Suzuki-Miyaura cross coupling of pyridine derivatives: A one-pot protocol to substituted azabiaryls. J Org Chem (2007) 72(5):1588-1594.
57. Smith AE, Clapham KM, Batsanov AS, Bryce MR, Tarbit B: (Dimethoxy- and dihalopyridyl)boronic acids and highly functionalized heteroarylpyridines by Suzuki cross-coupling reactions. Eur J Org Chem (2008) (8):1458-1463.
58. Clapham KM, Batsanov AS, Greenwood RD, Bryce MR, Smith AE, Tarbit B: Functionalized heteroarylpyridazines and pyridazin-3(2H)-one derivatives via palladium-catalyzed cross-coupling methodology. J Org Chem (2008) 73(6):2176-2181.
59. McLaughlin M, Marcantonio K, Chen C-Y, Davies IW: A simple, modular method for the synthesis of 3,4,5-trisubstituted pyrazoles. J Org Chem (2008) 73(11):4309-4312.
60. 2Mg· 2LiCl. Angew Chem Int Ed (2007) 46(40):7681-7684.
61. 2Mg·2LiCl. Angew Chem Int Ed (2008) 47(8):1503-1507.
62. 2·2LiCl: A chemoselective base for the directed zincation of sensitive arenes and heteroarenes. Angew Chem Int Ed (2007) 46(40):7685-7688. • Describes a new chemoselective complex base that directly affords organozinc species, which can cross-couple without additional manipulation.
63. L'Helgoual'ch J-M, Seggio A, Chevallier F, Yonehara M, Jeanneau E, Uchiyama M, Mongin F: Deprotonative metalation of five-membered aromatic heterocycles using mixed lithium-zinc species. J Org Chem (2008) 73(1):177-183.
64. Denmark SE, Baird JD, Regens CS: Palladium-catalyzed cross-coupling of five-membered heterocyclic silanolates. J Org Chem (2008) 73(4):1440-1455.
65. Zambon A, Borsato G, Brussolo S, Frascella P, Lucchini V: Efficient access to 5-substituted thiazoles by a novel metallotropic rearrangement. Tetrahedron Lett (2008) 49(1):66-69.
66. Pérez I, Sestelo JP, Sarandeses LA: Atom-efficient metal-catalyzed cross-coupling reaction of indium organometallics with organic electrophiles. J Am Chem Soc (2001) 123(18):4155-4160.
67. Pena MA, Sestelo JP, Sarandeses LA: Palladium-catalyzed aryl-aryl cross-coupling reaction using ortho-substituted arylindium reagents. J Org Chem (2007) 72(4):1271-1275. • Describes an ortho-metallation route to arylindium reagents, which are atom-economical as all three aryl ligands are readily cross-coupled.
68. Murata M, Ohara H, Oiwa R, Watanabe S, Masuda Y: Palladium(0)- catalyzed silylation of aryl halides with triorganosilanes: Synthesis of aryl(2-furyl)silanes. Synthesis (2006) (11):1771-1774.
69. Wulff WD, Peterson GA, Bauta WE, Chan K-S, Faron KL, Gilbertson SR, Kaesler RW, Yang DC, Murray CK: A regioselective entry to vinyl lithiums from unsymmetrical ketones via enol triflates. J Org Chem (1986) 51(2):277-279.
70. Murata M, Oyama T, Watanabe S, Masuda Y: Palladium-catalyzed borylation of aryl halides or triflates with dialkoxyborane: A novel and facile synthetic route to arylboronates. J Org Chem (2000) 65(1):164-168.
71. Murata M, Yamasaki H, Ueta T, Nagata M, Ishikura M, Watanabe S, Masuda Y: Synthesis of aryltriethoxysilanes via rhodium(I)-catalyzed cross-coupling of aryl electrophiles with triethoxysilane. Tetrahedron (2007) 63(19):4087-4094.
72. Iverson CN, Smith MR: Stoichiometric and catalytic B-C bond formation from unactivated hydrocarbons and boranes. J Am Chem Soc (1999) 121(33):7696-7697.
73. Cho J-Y, Iverson CN, Smith MR: Steric and chelate directing effects in aromatic borylation. J Am Chem Soc (2000) 122(51):12868- 12869.
74. Tse MK, Cho J-Y, Smith MR III: Regioselective aromatic borylation in an inert solvent. Org Lett (2001) 3(18):2831-2833.
75. Cho J-Y, Tse MK, Holmes D, Maleczka RE, Smith MR: Remarkably selective iridium catalysts for the elaboration of aromatic C-H bonds. Science (2002) 295(5553):305-308. •• Discloses (Ind)Ir(COD) as a catalyst for the direct borylation of unactivated arenes and provides an account of its development.
76. Ishiyama T, Takagi J, Ishida K, Miyaura N: Mild iridium-catalyzed borylation of arenes. High turnover numbers, room temperature reactions, and isolation of a potential intermediate. J Am Chem Soc (2002) 124(3):390-391.
77. Ishiyama T, Takagi J, Hartwig JF, Miyaura N: A stoichiometric aromatic C-H borylation catalyzed by iridium(I)/2,2′-bipyridine complexes at room temperature. Angew Chem Int Ed (2002) 41(16):3056-3058.
78. Ishiyama T, Takagi J, Nobuta Y, Miyaura N: Iridium-catalyzed C-H borylation of arenes and heteroarenes: 1-Chloro-3-iodo-5-(4,4,5,5-tetramethyl-1, 3,2-dioxaborolan-2-yl)benzene and 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- yl)indole. Org Synth (2005) 82:126-131.
79. Boller TM, Murphy JM, Hapke M, Ishiyama T, Miyaura N, Hartwig JF: Mechanism of the mild functionalization of arenes by diboron reagents catalyzed by iridium complexes. Intermediacy and chemistry of bipyridine-ligated iridium trisboryl complexes. J Am Chem Soc (2005) 127(41):14263-14278. •• Provides mechanistic insight into Ir-catalyzed borylations and the experimental section describes how to generate the active catalytic species from the [Ir(OMe)(COD)]2 pre-catalyst.
80. Chotana GA, Rak MA, Smith MR III: Sterically directed functionalization of aromatic C-H bonds: Selective borylation ortho to cyano groups in arenes and heterocycles. J Am Chem Soc (2005) 127(30):10539-10544.
81. Boebel TA, Hartwig JF: Silyl-directed, iridium-catalyzed ortho-borylation of arenes. A one-pot ortho-borylation of phenols, arylamines, and alkylarenes. J Am Chem Soc (2008) 130(24):7534-7535.
82. Kikuchi T, Nobuta Y, Umeda J, Yamamoto Y, Ishiyama T, Miyaura N: Practical synthesis of pinacolborane for one-pot synthesis of unsymmetrical biaryls via aromatic C-H borylation-cross-coupling sequence. Tetrahedron (2008) 64(22):4967-4971.
83. Maleczka RE Jr, Shi F, Holmes D, Smith MR III: C-H activation/borylation/oxidation: A one-pot unified route to meta-substituted phenols bearing ortho-/para-directing groups. J Am Chem Soc (2003) 125(26):7792-7793.
84. Shi F, Smith MR III, Maleczka RE Jr: Aromatic borylation/amidation/ oxidation: A rapid route to 5-substituted 3-amidophenols. Org Lett (2006) 8(7):1411-1414.
85. Holmes D, Chotana GA, Maleczka RE Jr, Smith MR III: One-pot borylation/amination reactions: Syntheses of arylamine boronate esters from halogenated arenes. Org Lett (2006) 8(7):1407-1410.
86. Murphy JM, Tzschucke CC, Hartwig JF: One-pot synthesis of arylboronic acids and aryl trifluoroborates by Ir-catalyzed borylation of arenes. Org Lett (2007) 9(5):757-760.
87. Takagi J, Sato K, Hartwig JF, Ishiyama T, Miyaura N: Iridium-catalyzed C-H coupling reaction of heteroaromatic compounds with bis(pinacolato)diboron: Regioselective synthesis of heteroarylboronates. Tetrahedron Lett (2002) 43(32):5649-5651.
88. Tagata T, Nishida M: Aromatic C-H borylation catalyzed by iridium/2,6-diisopropyl-N-(2-pyridylmethylene) aniline complex. Adv Synth Catal (2004) 346(13-15):1655-1660.
89. Mertins K, Zapf A, Beller M: Catalytic borylation of o-xylene and heteroarenes via C-H activation. J Mol Catal A Chem (2004) 207(1):21-25.
90. Mkhalid IA, Coventry DN, Albesa-Jove D, Batsanov AS, Howard JA, Perutz RN, Marder TB: Ir-catalyzed borylation of C-H bonds in N-containing heterocycles: Regioselectivity in the synthesis of heteroaryl boronate esters. Angew Chem Int Ed (2006) 45(3):489-491.
91. Kalyani D, Sanford MS: Regioselectivity in palladium-catalyzed C-H activation/oxygenation reactions. Org Lett (2005) 7(19):4149-4152.
92. Beck EM, Hatley R, Gaunt MJ: Synthesis of rhazinicine by a metal-catalyzed C-H bond functionalization strategy. Angew Chem Int Ed (2008) 47(16):3004-3007. • Describes a one-pot borylation/Suzuki sequence of N-Boc-pyrrole that is notable for its use of [Ir(Cl)(COD)]2, microwave irradiation and for being part of a total synthesis.
93. Paul S, Chotana GA, Holmes D, Reichle RC, Maleczka RE Jr, Smith MR III: Ir-catalyzed functionalization of 2-substituted indoles at the 7-position: Nitrogen-directed aromatic borylation. J Am Chem Soc (2006) 128(49):15552-15553.
94. Lo WF, Kaiser HM, Spannenberg A, Beller M, Tse MK: A highly selective Ir-catalyzed borylation of 2-substituted indoles: A new access to 2,7- and 2,4,7-substituted indoles. Tetrahedron Lett (2007) 48(3):371-375.
95. Chotana GA, Kallepalli VA, Maleczka RE Jr, Smith MR III: Iridium-catalyzed borylation of thiophenes: Versatile, synthetic elaboration founded on selective C-H functionalization. Tetrahedron (2008) 64(26):6103-6114. • Illustrates the application of Ir-catalyzed borylations to the field of heterocyclic chemistry.
96. Hata H, Shinokubo H, Osuka A: Highly regioselective Ir-catalyzed β-borylation of porphyrins via C-H bond activation and construction of β-β-linked diporphyrin. J Am Chem Soc (2005) 127(23):8264-8265.
97. Saiki T, Nishio Y, Ishiyama T, Miyaura N: Improvements of efficiency and regioselectivity in the iridium(I)-catalyzed aromatic C-H silylation of arenes with fluorodisilanes. Organometallics (2006) 25(26):6068-6073.
98. Ishiyama T, Sato K, Nishio Y, Miyaura N: Direct synthesis of aryl halosilanes through iridium(I)-catalyzed aromatic C-H silylation by disilanes. Angew Chem Int Ed (2003) 42(43):5346-5348.
99. Ishiyama T, Sato K, Nishio Y, Saiki T, Miyaura N: Regioselective aromatic C-H silylation of five-membered heteroarenes with fluorodisilanes catalyzed by iridium(I) complexes. Chem Commun (2005) (40):5065-5067.
100. Ezbiansky K, Djurovich PI, LaForest M, Sinning DJ, Zayes R, Berry DH: Catalytic C-H bond functionalization: Synthesis of arylsilanes by dehydrogenative transfer coupling of arenes and triethylsilane. Organometallics (1998) 17(8):1455-1457.
101. Kakiuchi F, Igi K, Matsumoto M, Chatani N, Murai S: Ruthenium- catalyzed dehydrogenative silylation of aryloxazolines with hydrosilanes via C-H bond cleavage. Chem Lett (2001) 30(5):422-423.
102. Kakiuchi F, Igi K, Matsumoto M, Hayamizu T, Chatani N, Murai S: A new chelation-assistance mode for a ruthenium-catalyzed silylation at the C-H bond in aromatic ring with hydrosilanes. Chem Lett (2002) 31(3):396-397.
103. Kakiuchi F, Matsumoto M, Tsuchiya K, Igi K, Hayamizu T, Chatani N, Murai S: The ruthenium-catalyzed silylation of aromatic C-H bonds with triethylsilane. J Organomet Chem (2003) 686(1-2):134-144.
104. Uchimau Y, Mouneer A, El Sayed M, Tanaka M: Selective arylation of a Si-H bond in O-bis(dimethylsilyl)benzene via C-H bond activation of arenes. Organometallics (1993) 12(6):2065-2069.
105. Williams NA, Uchimaru Y, Tanaka M: Platinum-catalyzed regioselective ortho-silylation of benzylideneamines via intramolecular C-H activation. J Chem Soc, Chem Commun (1995) 55(11):1129-1130.
106. Tsukada N, Hartwig JF: Intermolecular and intramolecular, platinum-catalyzed, acceptorless dehydrogenative coupling of hydrosilanes with aryl and aliphatic methyl C-H bonds. J Am Chem Soc (2005) 127(14):5022-5023.
107. Murata M, Fukuyama N, Wada J-Y, Watanabe S, Masuda Y: Platinum-catalyzed aromatic C-H silylation of arenes with 1,1,1,3,5,5,5-heptamethyltrisiloxane. Chem Lett (2007) 36(7):910-911. • Describes a one-pot iridium-catalyzed C-H activation/silylation/cross-coupling (also see reference [98]).
108. Mori A, Sugie A: Palladium-catalyzed CH arylation and dehydrogenative homocoupling of heteroaromatic compounds and application to the design of advanced organic materials. Bull Chem Soc Jpn (2008) 81(5):548-561.
109. Özdemir I, Demir S, Çetinkaya B, Gourlaouen C, Maseras F, Bruneau C, Dixneuf PH: Direct arylation of arene C-H bonds by cooperative action of NHcarbene-ruthenium(II) catalyst and carbonate via proton abstraction mechanism. J Am Chem Soc (2008) 130(4):1156-1157.
110. Bedford RB, Betham M, Caffyn AJ, Charmant JP, Lewis-Alleyne LC, Long PD, Polo-Cerón D, Prashar S: Simple rhodium-chlorophosphine pre-catalysts for the ortho-arylation of phenols. Chem Commun (2008) (8):990-992.
111. Flegeau EF, Popkin ME, Greaney MF: Direct arylation of oxazoles at C2. A concise approach to consecutively linked oxazoles. Org Lett (2008) 10(13):2717-2720.
112. Do H-Q, Daugulis O: Copper-catalyzed arylation of heterocycle C-H bonds. J Am Chem Soc (2007) 129(41):12404-12405.
113. Campeau L-C, Bertrand-Laperle M, Leclerc J-P, Villemure E, Gorelsky S, Fagnou K: C2, C5, and C4 azole N-oxide direct arylation including room-temperature reactions. J Am Chem Soc (2008) 130(11):3276-3277.
114. Ohnmacht SA, Mamone P, Culshaw AJ, Greaney MF: Direct arylations on water: Synthesis of 2,5-disubstituted oxazoles balsoxin and texaline. Chem Commun (2008) (10):1241-1243.
115. Lewis JC, Berman AM, Bergman RG, Ellman JA: Rh(I)-catalyzed arylation of heterocycles via C-H bond activation: Expanded scope through mechanistic insight. J Am Chem Soc (2008) 130(8):2493-2500. • The chemistry described can be performed without the use of a dry box.
116. Stuart DR, Fagnou K: The catalytic cross-coupling of unactivated arenes. Science (2007) 316(5828):1172-1175. •• Reports a halogen-free method for arylating indoles and superbly illustrates and describes the challenges associated with two-fold functionalization/ direct arylation protocols.
117. Dwight TA, Rue NR, Charyk D, Josselyn R, DeBoef B: C-C bond formation via double C-H functionalization: Aerobic oxidative coupling as a method for synthesizing heterocoupled biaryls. Org Lett (2007) 9(16):3137-3139. • Readers interested in the chemistry of reference [116] will want to be aware of this equally green direct arylation method by which complementary regioselectivities can be observed.
118. Li B-J, Tian S-L, Fang Z, Shi Z-J: Multiple C-H activations to construct biologically active molecules in a process completely free of organohalogen and organometallic components. Angew Chem Int Ed (2008) 47(6):1115-1118.
119. Brasche G, García-Fortanet J, Buchwald SL: Twofold C-H functionalization: Palladium-catalyzed ortho arylation of anilides. Org Lett (2008) 10(11):2207-2210. • Describes a method that expands the versatility of two-fold C-H functionalizations by alleviating past structural and stochiometric constraints.
120. Hull KL, Sanford MS: Catalytic and highly regioselective cross-coupling of aromatic C-H substrates. J Am Chem Soc (2007) 129(39):11904-11905.
121. Li X, Hewgley JB, Mulrooney CA, Yang J, Kozlowski MC: Enantioselective oxidative biaryl coupling reactions catalyzed by 1,5-diazadecalin metal complexes: Efficient formation of chiral functionalized BINOL derivatives. J Org Chem (2003) 68(14):5500-5511.
122. Oi S, Sato H, Sugawara S, Inoue Y: Nitrogen-directed ortho-selective homocoupling of aromatic compounds catalyzed by ruthenium complexes. Org Lett (2008) 10(9):1823-1826.