Transition metal catalyzed synthesis of aryl sulfides

Molecules

Volumn 16, Issue 1, 2011, Pages 590-608

  Eichman, Chad C ^a   Stambuli, James P ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

Arylation of thiols; Biaryl sulfides; C S bond formation

Indexed keywords

SULFIDE; TRANSITION ELEMENT;

CATALYSIS; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REVIEW;

CATALYSIS; MAGNETIC RESONANCE SPECTROSCOPY; SULFIDES; TRANSITION ELEMENTS;

EID: 79251500709     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules16010590     Document Type: Review

References (108)

1. Sun, Z. Y.; Botros, E.; Su, A. D.; Kim, Y.; Wang, E. J.; Baturay, N. Z.; Kwon, C. H. Sulfoxidecontaining aromatic nitrogen mustards as hypoxia-directed bioreductive cytotoxins. J. Med. Chem. 2000, 43, 4160-4168.
2. Wang, Y. G.; Chackalamannil, S.; Hu, Z. Y.; Clader, J. W.; Greenlee, W.; Billard, W.; Binch, H.; Crosby, G.; Ruperto, V.; Duffy, R. A.; McQuade, R.; Lachowicz, J. E. Design and synthesis of piperidinyl piperidine analogues as potent and selective M-2 muscarinic receptor antagonists. Biorg. Med. Chem. Lett. 2000, 10, 2247-2250.
3. Nielsen, S. F.; Nielsen, E. O.; Olsen, G. M.; Liljefors, T.; Peters, D. Novel potent ligands for the central nicotinic acetylcholine receptor: Synthesis, receptor binding, and 3D-QSAR analysis. J. Med. Chem. 2000, 43, 2217-2226.
4. Liu, G.; Huth, J. R.; Olejniczak, E. T.; Mendoza, R.; DeVries, P.; Leitza, S.; Reilly, E. B.; Okasinski, G. F.; Fesik, S. W.; von Geldern, T. W. Novel p-arylthio cinnamides as antagonists of leukocyte function-associated antigen-1/intracellular adhesion molecule-1 interaction. 2. Mechanism of inhibition and structure-based improvement of pharmaceutical properties. J. Med. Chem. 2001, 44, 1202-1210.
5. Clader, J. W.; Billard, W.; Binch, H.; Chen, L. Y.; Crosby, G.; Duffy, R. A.; Ford, J.; Kozlowski, J. A.; Lachowicz, J. E.; Li, S. J.; Liu, C.; McCombie, S. W.; Vice, S.; Zhou, G. W.; Greenlee, W. J. Muscarinic M2 antagonists: anthranilamide derivatives with exceptional selectivity and in vivo activity. Biorg. Med. Chem. 2004, 12, 319-326.
6. Otzen, T.; Wempe, E. G.; Kunz, B.; Bartels, R.; Lehwark-Yvetot, G.; Hansel, W.; Schaper, K. J.; Seydel, J. K. Folate-synthesizing enzyme system as target for development of inhibitors and inhibitor combinations against Candida albicans-synthesis and biological activity of new 2,4-diaminopyrimidines and 4 '-substituted 4-aminodiphenyl sulfones. J. Med. Chem. 2004, 47, 240-253.
7. Alcaraz, M. L.; Atkinson, S.; Cornwall, P.; Foster, A. C.; Gill, D. M.; Humphries, L. A.; Keegan, P. S.; Kemp, R.; Merifield, E.; Nixon, R. A.; Noble, A. J.; O'Beirne, D.; Patel, Z. M.; Perkins, J.; Rowan, P.; Sadler, P.; Singleton, J. T.; Tornos, J.; Watts, A. J.; Woodland, I. A. Efficient syntheses of AZD4407 via thioether formation by nucleophilic attack of organometallic species on sulphur. Org. Process Res. Dev. 2005, 9, 555-569.
8. Llauger, L.; He, H. Z.; Kim, J.; Aguirre, J.; Rosen, N.; Peters, U.; Davies, P.; Chiosis, G. Evaluation of 8-arylsulfanyl, 8-arylsulfoxyl, and 8-arylsulfonyl adenine derivatives as inhibitors of the heat shock protein 90. J. Med. Chem. 2005, 48, 2892-2905.
9. Gangjee, A.; Zeng, Y. B.; Talreja, T.; McGuire, J. J.; Kisliuk, R. L.; Queener, S. F. Design and synthesis of classical and nonclassical 6-arylthio-2, 4-diamino-5-ethylpyrrolo[2, 3-d]pyrimidines as antifolates. J. Med. Chem. 2007, 50, 3046-3053.
10. Labelle, M.; Belley, M.; Gareau, Y.; Gauthier, J. Y.; Guay, D.; Gordon, R.; Grossman, S. G.; Jones, T. R.; Leblanc, Y.; McAuliffe, M.; McFarlane, C.; Masson, P.; Metters, K. M.; Ouimet, N.; Patrick, D. H.; Piechuta, H.; Rochette, C.; Sawyer, N.; Xiang, Y. B.; Pickett, C. B.; Fordhutchinson, A. W.; Zamboni, R. J.; Young, R. N. Discovery of Mk-0476, a Potent and Orally-Active Leukotriene D-4 Receptor Antagonist Devoid of Peroxisomal Enzyme-Induction. Biorg. Med. Chem. Lett. 1995, 5, 283-288.
11. Pasquini, S.; Mugnaini, C.; Tintori, C.; Botta, M.; Trejos, A.; Arvela, R. K.; Larhed, M.; Witvrouw, M.; Michiels, M.; Christ, F.; Debyser, Z.; Corelli, F. Investigations on the 4-quinolone-3-carboxylic acid motif. 1. Synthesis-activity relationship of a class of human immunodeficiency virus type 1 integrase inhibitors. J. Med. Chem. 2008, 51, 5125-5129.
12. Bichler, P.; Love, J. A. Organometallic Approaches to Carbon-Sulfur Bond Formation. C-X Bond Formation 2010, 31, 39-64.
13. Kosugi, M.; Shimizu, T.; Migita, T. Reactions of Aryl Halides with Thiolate Anions in Presence of Catalytic Amounts of Tetrakis (Triphenylphosphine) Palladium Preparation of Aryl Sulfides. Chem. Lett. 1978, 13-14.
14. Migita, T.; Shimizu, T.; Asami, Y.; Shiobara, J.; Kato, Y.; Kosugi, M. The Palladium Catalyzed Nucleophilic-Substitution of Aryl Halides by Thiolate Anions. Bull. Chem. Soc. Jpn. 1980, 53, 1385-1389.
15. Murahashi, S. I.; Yamamura, M.; Yanagisawa, K.; Mita, N.; Kondo, K. Stereoselective Synthesis of Alkenes and Alkenyl Sulfides from Alkenyl Halides Using Palladium and Ruthenium Catalysts. J. Org. Chem. 1979, 44, 2408-2417.
16. Kosugi, M.; Ogata, T.; Terada, M.; Sano, H.; Migita, T. Palladium-Catalyzed Reaction of Stannyl Sulfide with Aryl Bromide - Preparation of Aryl Sulfide. Bull. Chem. Soc. Jpn. 1985, 58, 3657-3658.
17. Carpita, A.; Rossi, R.; Scamuzzi, B. Palladium - Catalyzed-Reactions of Trialkylstannyl Phenyl Sulfides with Alkenyl Bromides - a New Diastereoselective Synthesis of (E)-1-Alkenyl Phenyl Sulfides. Tetrahedron Lett. 1989, 30, 2699-2702.
18. Baranano, D.; Hartwig, J. F. Carbon-Heteroatom Bond-Forming Reductive Elimination - Mechanism, Importance of Trapping Reagents, and Unusual Electronic Effects during Formation of Aryl Sulfides. J. Am. Chem. Soc. 1995, 117, 2937-2938.
19. Ciattini, P. G.; Morera, E.; Ortar, G. A New, Palladium-Catalyzed Synthesis of Aromatic Mercapturic Acid-Derivatives. Tetrahedron Lett. 1995, 36, 4133-4136.
20. Louie, J.; Hartwig, J. F. Transmetalation Involving Organotin Aryl, Thiolate, and Amide Compounds - an Unusual Type of Dissociative Ligand Substitution-Reaction. J. Am. Chem. Soc. 1995, 117, 11598-11599.
21. Ishiyama, T.; Mori, M.; Suzuki, A.; Miyaura, N. The palladium-catalyzed cross-coupling reaction of 9-organothio-9-borabicyclo[3.3.1]nonanes with organic electrophiles: Synthesis of unsymmetrical sulfides. J. Organomet. Chem. 1996, 525, 225-231.
22. Hartwig, J. F. Carbon, àíHeteroatom Bond-Forming Reductive Eliminations of Amines, Ethers, and Sulfides. Acc. Chem. Res. 1998, 31, 852-860.
23. Mann, G.; Baranano, D.; Hartwig, J. F.; Rheingold, A. L.; Guzei, I. A. Carbon-sulfur bond-forming reductive elimination involving sp-, sp (2)-, and sp (3)-hybridized carbon. Mechanism, steric effects, and electronic effects on sulfide formation. J. Am. Chem. Soc. 1998, 120, 9205-9219.
24. Zheng, N.; McWilliams, J. C.; Fleitz, F. J.; Armstrong, J. D.; Volante, R. P. Palladium-Catalyzed Synthesis of Aryl Sulfides from Aryl Triflates. J. Org. Chem. 1998, 63, 9606-9607.
25. Li, G. Y. The First Phosphine Oxide Ligand Precursors for Transition Metal Catalyzed Cross-Coupling Reactions: C-C, C-N, and C-S Bond Formation on Unactivated Aryl Chlorides. Angew. Chem. Int. Ed. 2001, 40, 1513-1516.
26. Li, G. Y.; Zheng, G.; Noonan, A. F. Highly active, air-stable versatile palladium catalysts for the C-C, C-N, and C-S bond formations via cross-coupling reactions of aryl chlorides. J. Org. Chem. 2001, 66, 8677-8681.
27. Savarin, C.; Srogl, J.; Liebeskind, L. S. Substituted alkyne synthesis under nonbasic conditions: Copper carboxylate-mediated, palladium-catalyzed thioalkyne-boronic acid cross-coupling. Org. Lett. 2001, 3, 91-93.
28. Schopfer, U.; Schlapbach, A. A general palladium-catalysed synthesis of aromatic and heteroaromatic thioethers. Tetrahedron 2001, 57, 3069-3073.
29. Cacchi, S.; Fabrizi, G.; Goggiamani, A.; Parisi, L. M. Unsymmetrical Diaryl Sulfones through Palladium-Catalyzed Coupling of Aryl Iodides and Arenesulfinates. Org. Lett. 2002, 4, 4719-4721.
30. Li, G. Y. Highly Active, Air-Stable Palladium Catalysts for the C-C and C-S Bond-Forming Reactions of Vinyl and Aryl Chlorides: Use of Commercially Available [(t-Bu) 2P (OH)]2PdCl2, [(t-Bu) 2P (OH) PdCl2]2, and [[(t-Bu) 2PO-H-OP (t-Bu) 2]PdCl]2 as Catalysts. J. Org. Chem. 2002, 67, 3643-3650.
31. Bandgar, B. P.; Bettigeri, S. V.; Phopase, J. Unsymmetrical diaryl Sulfones through palladiumcatalyzed coupling of aryl boronic acids and arylsulfonyl chlorides. Org. Lett. 2004, 6, 2105-2108.
32. Itoh, T.; Mase, T. A general palladium-catalyzed coupling of aryl bromides/triflates and thiols. Org. Lett. 2004, 6, 4587-4590.
33. Lengar, A.; Kappe, C. O. Tunable carbon-carbon and carbon-sulfur cross-coupling of boronic acids with 3, 4-dihydropyrimidine-2-thiones. Org. Lett. 2004, 6, 771-774.
34. Murata, M.; Buchwald, S. L. A general and efficient method for the palladium-catalyzed crosscoupling of thiols and secondary phosphines. Tetrahedron 2004, 60, 7397-7403.
35. Kreis, M.; Brase, S. A general and efficient method for the synthesis of silyl-protected arenethiols from aryl halides or triflates. Adv. Synth. Catal. 2005, 347, 313-319.
36. Mispelaere-Canivet, C.; Spindler, J. F.; Perrio, S.; Beslin, P. Pd-2 (dba) (3)/Xantphos-catalyzed cross-coupling of thiols and aryl bromides/triflates. Tetrahedron 2005, 61, 5253-5259.
37. Moreau, X.; Campagne, J. M.; Meyer, G.; Jutand, A. Palladium-catalyzed C-S bond formation: Rate and mechanism of the coupling of aryl or vinyl halides with a thiol derived from a cysteine. Eur. J. Org. Chem. 2005, 3749-3760.
38. Cai, L.; Cuevas, J.; Peng, Y. Y.; Pike, V. W. Rapid palladium-catalyzed cross-coupling in the synthesis of aryl thioethers under microwave conditions. Tetrahedron Lett. 2006, 47, 4449-4452.
39. Fukuzawa, S.; Tanihara, D.; Kikuchi, S. Palladium-catalyzed coupling reaction of diaryl dichalcogenide with aryl bromide leading to the synthesis of unsymmetrical aryl chalcogenide. Synlett 2006, 2145-2147.
40. Maitro, G.; Vogel, S.; Prestat, G.; Madec, D.; Poli, G. Aryl sulfoxides via palladium-catalyzed arylation of sulfenate anions. Org. Lett. 2006, 8, 5951-5954.
41. Ranu, B. C.; Chattopadhyay, K.; Banerjee, S. Indium (l) iodide promoted cleavage of diphenyl diselenide and disulfide and subsequent palladium (0)-catalyzed condensation with vinylic bromides. A simple one-pot synthesis of vinylic selenides and sulfides. J. Org. Chem. 2006, 71, 423-425.
42. Willis, M. C.; Taylor, D.; Gillmore, A. T. Palladium-catalysed intramolecular enolate O-arylation and thio-enolate S-arylation: synthesis of benzo[b]furans and benzo[b]thiophenes. Tetrahedron 2006, 62, 11513-11520.
43. Hartwig, J. F. Electronic Effects on Reductive Elimination To Form Carbon-Carbon and Carbon-Heteroatom Bonds from Palladium (II) Complexes. Inorg. Chem. 2007, 46, 1936-1947.
44. Maitro, G.; Vogel, S.; Sadaoui, M.; Prestat, G.; Madec, D.; Poli, G. Enantioselective Synthesis of Aryl Sulfoxides via Palladium-Catalyzed Arylation of Sulfenate Anions. Org. Lett. 2007, 9, 5493-5496.
45. Dahl, T.; Tornoe, C. W.; Bang-Andersen, B.; Nielsen, P.; Jorgensen, M. Palladium-catalyzed three-component approach to promazine with formation of one carbon-sulfur and two carbonnitrogen bonds. Angew. Chem. Int. Ed. 2008, 47, 1726-1728.
46. Hartwig, J. F. Carbon-heteroatom bond formation catalysed by organometallic complexes. Nature 2008, 455, 314-322.
47. Lee, J.-Y.; Lee, P. H. Palladium-Catalyzed Carbon, àíSulfur Cross-Coupling Reactions with Indium Tri (organothiolate) and Its Application to Sequential One-Pot Processes. J. Org. Chem. 2008, 73, 7413-7416.
48. Norris, T.; Leeman, K. Development of a new variant of the migita reaction for carbon-sulfur bond formation used in the manufacture of tetrahydro-4-[3-[4-(2-methyl-1H-imidazol-1-yl) phenyl]thio]phenyl-2H-pyran-4- carboxamide. Org. Process Res. Dev. 2008, 12, 869-876.
49. Alvaro, E.; Hartwig, J. F. Resting State and Elementary Steps of the Coupling of Aryl Halides with Thiols Catalyzed by Alkylbisphosphine Complexes of Palladium. J. Am. Chem. Soc. 2009, 131, 7858-7868.
50. Bryan, C. S.; Braunger, J. A.; Lautens, M. Efficient Synthesis of Benzothiophenes by an Unusual Palladium-Catalyzed Vinylic C-S Coupling. Angew. Chem. Int. Ed. 2009, 48, 7064-7068.
51. Duan, Z. Y.; Ranjit, S.; Zhang, P. F.; Liu, X. G. Synthesis of Aryl Sulfides by Decarboxylative C-S Cross-Couplings. Chem. Eur. J. 2009, 15, 3666-3669.
52. Eichman, C. C.; Stambuli, J. P. Zinc-Mediated Palladium-Catalyzed Formation of Carbon-Sulfur Bonds. J. Org. Chem. 2009, 74, 4005-4008.
53. Jiang, Z.; She, J.; Lin, X. F. Palladium on Charcoal as a Recyclable Catalyst for C-S Cross-Coupling of Thiols with Aryl Halides under Ligand-Free Conditions. Adv. Synth. Catal. 2009, 351, 2558-2562.
54. Fernandez-Rodriguez, M. A.; Shen, Q. L.; Hartwig, J. F. Highly efficient and functional-grouptolerant catalysts for the palladium-catalyzed coupling of aryl chlorides with thiols. Chem. Eur. J. 2006, 12, 7782-7796.
55. Fernandez-Rodriguez, M. A.; Shen, Q. L.; Hartwig, J. F. A general and long-lived catalyst for the palladium-catalyzed coupling of aryl halides with thiols. J. Am. Chem. Soc. 2006, 128, 2180-2181.
56. Tokuyama, H.; Yokoshima, S.; Yamashita, T.; Fukuyama, T. A novel ketone synthesis by a palladium-catalyzed reaction of thiol esters and organozinc reagents. Tetrahedron Lett. 1998, 39, 3189-3192.
57. Cristau, H. J.; Chabaud, B.; Chene, A.; Christol, H. Synthesis of Diaryl Sulfides by Nickel (Ii) - Catalyzed Arylation of Arenethiolates. Synthesis-Stuttgart 1981, 892-894.
58. Percec, V.; Bae, J. Y.; Hill, D. H. Aryl Mesylates in Metal-Catalyzed Homo-Coupling and Cross-Coupling Reactions.4. Scope and Limitations of Aryl Mesylates in Nickel-Catalyzed Cross-Coupling Reactions. J. Org. Chem. 1995, 60, 6895-6903.
59. Takagi, K. Nucleophilic Displacement Catalyzed by Transition-Metal.7. Nickel (0)-Catalyzed Synthesis of Diaryl Sulfides from Aryl Halides and Aromatic Thiols. Chem. Lett. 1987, 2221-2224.
60. Millois, C.; Diaz, P. Solution-phase synthesis of diaryl selenides using polymer-supported borohydride. Org. Lett. 2000, 2, 1705-1708.
61. Baldovino-Pantaleon, O.; Hernandez-Ortega, S.; Morales-Morales, D. Alkyl-and arylthiolation of aryl halides catalyzed by fluorinated bis-imino-nickel NNN pincer complexes [NiCl2{C5H3N-2,6-(CHNArf) (2)}]. Adv. Synth. Catal. 2006, 348, 236-242.
62. Gomez-Benitez, V.; Baldovino-Pantaleon, O.; Herrera-Alvarez, C.; Toscano, R. A.; Morales-Morales, D. High yield thiolation of iodobenzene catalyzed by the phosphinite nickel PCP pincer complex: [NiCl{C6H3-2,6-(OPPh2) (2)}]. Tetrahedron Lett. 2006, 47, 5059-5062.
63. Yatsumonji, Y.; Okada, O.; Tsubouchi, A.; Takeda, T. Stereo-recognizing transformation of (E) - alkenyl halides into sulfides catalyzed by nickel (0) triethyl phosphite complex. Tetrahedron 2006, 62, 9981-9987.
64. Yatsumonji, Y.; Ishida, Y.; Tsubouchi, A.; Takeda, T. Nickel (0) triethyl phosphite complexcatalyzed allylic substitution with retention of regio-and stereochemistry. Org. Lett. 2007, 9, 4603-4606.
65. Jammi, S.; Barua, P.; Rout, L.; Saha, P.; Punnlyamurthy, T. Efficient ligand-free nickel-catalyzed C-S cross-coupling of thiols with aryl iodides. Tetrahedron Lett. 2008, 49, 1484-1487.
66. Zhang, Y. G.; Ngeow, K. C.; Ying, J. Y. The first n-heterocyclic carbene-based nickel catalyst for C-S coupling. Org. Lett. 2007, 9, 3495-3498.
67. Palomo, C.; Oiarbide, M.; Lopez, R.; Gomez-Bengoa, E. Phosphazene bases for the preparation of biaryl thioethers from aryl iodides and arenethiols. Tetrahedron Lett. 2000, 41, 1283-1286.
68. Kwong, F. Y.; Buchwald, S. L. A general, efficient, and inexpensive catalyst system for the coupling of aryl iodides and thiols. Org. Lett. 2002, 4, 3517-3520.
69. Wan, Z. H.; Jones, C. D.; Koenig, T. M.; Pu, Y. J.; Mitchell, D. Vinyl aryl ethers from coppercatalyzed coupling of vinyl halides and phenols. Tetrahedron Lett. 2003, 44, 8257-8259.
70. Bates, C. G.; Saejueng, P.; Doherty, M. Q.; Venkataraman, D. Copper-Catalyzed Synthesis of Vinyl Sulfides. Org. Lett. 2004, 6, 5005-5008.
71. Cristau, H. J.; Cellier, P. P.; Spindler, J. F.; Taillefer, M. Highly efficient and mild copper-catalyzed N-and C-arylations with aryl bromides and iodides. Chem. Eur. J. 2004, 10, 5607-5622.
72. Zhu, W.; Ma, D. Synthesis of Aryl Sulfones via l-Proline-Promoted CuI-Catalyzed Coupling Reaction of Aryl Halides with Sulfinic Acid Salts. J. Org. Chem. 2005, 70, 2696-2700.
73. Chen, Y.-J.; Chen, H.-H. 1, 1, 1-Tris (hydroxymethyl) ethane as a New, Efficient, and Versatile Tripod Ligand for Copper-Catalyzed Cross-Coupling Reactions of Aryl Iodides with Amides, Thiols, and Phenols. Org. Lett. 2006, 8, 5609-5612.
74. Enguehard-Gueiffier, C.; Thery, I.; Gueiffier, A.; Buchwald, S. L. A general and efficient method for the copper-catalyzed cross-coupling of amides and thiophenols with 6-halogenoimidazo[1,2-alpha]pyridines. Tetrahedron 2006, 62, 6042-6049.
75. Evindar, G.; Batey, R. A. Parallel synthesis of a library of benzoxazoles and benzothiazoles using ligand-accelerated copper-catalyzed cyclizations of ortho-halobenzanilides. J. Org. Chem. 2006, 71, 1802-1808.
76. Krafft, E. A.; Pinard, E.; Thomas, A. W. An improved synthesis of Lu AA20465. Tetrahedron Lett. 2006, 47, 5355-5357.
77. Kumar, S.; Engman, L. Microwave-assisted copper-catalyzed preparation of diaryl chalcogenides. J. Org. Chem. 2006, 71, 5400-5403.
78. Sawada, N.; Itoh, T.; Yasuda, N. Efficient copper-catalyzed coupling of aryl iodides and thiobenzoic acid. Tetrahedron Lett. 2006, 47, 6595-6597.
79. Taniguchi, N. Aryl-or alkylation of diaryl disulfides using organoboronic acids and a copper catalyst. Synlett 2006, 1351-1354.
80. Zheng, Y. F.; Du, X. F.; Bao, W. L. L-proline promoted cross-coupling of vinyl bromide with thiols catalyzed by CuBr in ionic liquid. Tetrahedron Lett. 2006, 47, 1217-1220.
81. Zhu, D.; Xu, L.; Wu, F.; Wan, B. S. A mild and efficient copper-catalyzed coupling of aryl iodides and thiols using an oxime-phosphine oxide ligand. Tetrahedron Lett. 2006, 47, 5781-5784.
82. Rout, L.; Sen, T. K.; Punniyamurthy, T. Efficient CuO-nanoparticle- catalyzed C-S cross-coupling of thiols with iodobenzene. Angew. Chem. Int. Ed. 2007, 46, 5583-5586.
83. Taniguchi, N. Convenient synthesis of unsymmetrical organochalcogenides using organoboronic acids with dichalcogenides via cleavage of the S-S, Se-Se, or Te-Te bond by a copper catalyst. J. Org. Chem. 2007, 72, 1241-1245.
84. Verma, A. K.; Singh, J.; Chaudhary, R. A general and efficient CuI/BtH catalyzed coupling of aryl halides with thiols. Tetrahedron Lett. 2007, 48, 7199-7202.
85. Wang, Z. M.; Mo, H. J.; Bao, W. L. Mild, efficient and highly stereoselective synthesis of (Z)-vinyl chalcogenides from vinyl bromides catalyzed by copper (I) in ionic liquids based on amino acids. Synlett 2007, 91-94.
86. Zhang, H.; Cao, W. G.; Ma, D. W. L-proline-promoted CuI-Catalyzed C-S bond formation between aryl iodides and thiols. Synth. Commun. 2007, 37, 25-35.
87. Buranaprasertsuk, P.; Chang, J. W. W.; Chavasiri, W.; Chan, P. W. H. Copper-catalyzed Ullmann coupling under ligand-and additive-free conditions. Part 2: S-arylation of thiols with aryl iodides. Tetrahedron Lett. 2008, 49, 2023-2025.
88. Evano, G.; Blanchard, N.; Toumi, M. Copper-mediated coupling reactions and their applications in natural products and designed biomolecules synthesis. Chem. Rev. 2008, 108, 3054-3131.
89. Guo, S. R.; Yuan, Y. Q. CuI/L-proline-catalyzed synthesis of vinyl sulfides in 95% alcohol. Synth. Commun. 2008, 38, 2722-2730.
90. Jiang, B.; Tian, H.; Huang, Z. G.; Xu, M. Successive copper (I)-catalyzed cross-couplings in one pot: A novel and efficient starting point for synthesis of carbapenems. Org. Lett. 2008, 10, 2737-2740.
91. Kabir, M. H.; Van Linn, M. L.; Monte, A.; Cook, J. M. Stereo-and regiospecific Cu-catalyzed, cross-coupling reaction of vinyl iodides and thiols: A very mild and general route for the synthesis of vinyl sulfides. Org. Lett. 2008, 10, 3363-3366.
92. Sperotto, E.; van Klink, G. P. M.; de Vries, J. G.; van Koten, G. Ligand-free copper-catalyzed C-S coupling of aryl iodides and thiols. J. Org. Chem. 2008, 73, 5625-5628.
93. Xu, H.-J.; Zhao, X.-Y.; Fu, Y.; Feng, Y.-S. Ligand-Free C-S Bond Formation Catalyzed by Copper (I) Oxide. Synlett 2008, 2008, 3063, 3067.
94. Bagley, M. C.; Dix, M. C.; Fusillo, V. Rapid Ullmann-type synthesis of aryl sulfides using a copper (I) catalyst and ligand under microwave irradiation. Tetrahedron Lett. 2009, 50, 3661-3664.
95. Haldon, E.; Alvarez, E.; Nicasio, M. C.; Perez, P. J. Dinuclear Copper (I) Complexes as Precatalysts in Ullmann and Goldberg Coupling Reactions. Organometallics 2009, 28, 3815-3821.
96. Luo, P. S.; Wang, F.; Li, J. H.; Tang, R. Y.; Zhong, P. Copper-Catalyzed Selective S-Arylation of 1, 2-Bis (o-amino-1H-pyrazolyl) Disulfides with Arylboronic Acids. Synthesis-Stuttgart 2009, 921-928.
97. Luo, P. S.; Yu, M.; Tang, R. Y.; Zhong, P.; Li, J. H. Solvent-free copper-catalyzed oxidative S-arylation of 1,2-diaryldisulfides with aryltrimethoxysilane. Tetrahedron Lett. 2009, 50, 1066-1070.
98. Ma, D. W.; Xie, S. W.; Xue, P.; Zhang, X. J.; Dong, J. H.; Jiang, Y. W. Efficient and Economical Access to Substituted Benzothiazoles: Copper-Catalyzed Coupling of 2-Haloanilides with Metal Sulfides and Subsequent Condensation. Angew. Chem. Int. Ed. 2009, 48, 4222-4225.
99. Murru, S.; Ghosh, H.; Sahoo, S. K.; Patel, B. K. Intra-and Intermolecular C-S Bond Formation Using a Single Catalytic System: First Direct Access to Arylthiobenzothiazoles. Org. Lett. 2009, 11, 4254-4257.
100. Prasad, D. J. C.; Naidu, A. B.; Sekar, G. An efficient intermolecular C (aryl)-S bond forming reaction catalyzed by BINAM-copper (II) complex. Tetrahedron Lett. 2009, 50, 1411-1415.
101. She, J.; Jiang, Z.; Wang, Y. G. Simple, efficient and recyclable catalytic system for performing copper-catalyzed C-S coupling of thiols with aryl iodides in PEG and PEG-H2O. Tetrahedron Lett. 2009, 50, 593-596.
102. Zhao, Q. W.; Li, L.; Fang, Y. W.; Sun, D. Q.; Li, C. Z. "Ligand-Free" CuI-Catalyzed Highly Efficient Intramolecular S-Vinylation of Thiols with Vinyl Chlorides and Bromides. J. Org. Chem. 2009, 74, 459-462.
103. Ranu, B. C.; Saha, A.; Jana, R. Microwave-Assisted Simple and Efficient Ligand Free Copper Nanoparticle Catalyzed Aryl-Sulfur Bond Formation. Adv. Synth. Catal. 2007, 349, 2690-2696.
104. Bhadra, S.; Sreedhar, B.; Ranu, B. C. Recyclable Heterogeneous Supported Copper-Catalyzed Coupling of Thiols with Aryl Halides: Base-Controlled Differential Arylthiolation of Bromoiodobenzenes. Adv. Synth. Catal. 2009, 351, 2369-2378.
105. Savarin, C.; Srogl, J.; Liebeskind, L. S. A mild, nonbasic synthesis of thioethers. The coppercatalyzed coupling of boronic acids with N-thio (alkyl, aryl, heteroaryl) imides. Org. Lett. 2002, 4, 4309-4312.
106. Correa, A.; Carril, M.; Bolm, C. Iron-catalyzed S-arylation of thiols with aryl iodides. Angew. Chem. Int. Ed. 2008, 47, 2880-2883.
107. Buchwald, S. L.; Bolm, C. On the Role of Metal Contaminants in Catalyses with FeCl3. Angew. Chem. Int. Ed. 2009, 48, 5586-5587.
108. Wong, Y. C.; Jayanth, T. T.; Cheng, C. H. Cobalt-catalyzed aryl-sulfur bond formation. Org. Lett. 2006, 8, 5613-5616.