Efficient Copper-Catalyzed S-Arylation
of Thiols with Aryl Bromides and Chlorides

Yaming Li; Xiaoying Li; Huifeng Wang; Tao Chen; Yusheng Xie

doi:10.1055/s-0030-1258234

PAPER

Efficient Copper-Catalyzed S-Arylation of Thiols with Aryl Bromides and Chlorides

Yaming Li*, Xiaoying Li, Huifeng Wang, Tao Chen, Yusheng Xie
State Key Laboratory of Fine Chemicals, School of Chemical Engineering, Dalian University of Technology, Dalian 116012, P. R. of China
Fax: +86(411)39893900; e-Mail: yamingli@chem.dlut.edu.cn;

Abstract

All articles of this category

Abstract

An efficient copper-catalyzed system for C-S cross-coupling of aromatic thiols with aryl bromides and chlorides has been developed using 1,2,3,4-tetrahydroquinoline-8-ol as a ligand. It is noteworthy that this method is proved to be especially effective for aryl bromides with electron-donating groups. By this protocol, a variety of thioethers as well as symmetrical and unsymmetrical bis-thioethers are obtained in excellent yields with an exceptional level of functional group tolerance and high chemoselectivity.

Key words

copper catalyst - aryl bromides - aryl chlorides - cross-coupling - organic sulfides

Full Text

References

<A NAME="RF10410SS-1A">1a</A> Liu LP. Stelmach JE. Natarajan SR. Chen MH. Singh SB. Schwartz CD. Fitzgerald CE. O’Keefe SJ. Zaller DM. Schmatz DM. Doherty JB. Bioorg. Med. Chem. Lett. 2003, 13: 3979

<A NAME="RF10410SS-1B">1b</A> Procter DJ. J. Chem. Soc., Perkin Trans. 1 2000, 835

<A NAME="RF10410SS-1C">1c</A> Procter DJ. J. Chem. Soc., Perkin Trans. 1 2001, 335

<A NAME="RF10410SS-1D">1d</A> Corbet JP. Mignani G. Chem. Rev. 2006, 106: 2651

<A NAME="RF10410SS-2">2</A> De Martino G. Edler MC. La Regina G. Coluccia A. Barbera MC. Barrow D. Nicholson RI. Chiosis G. Brancale A. Hamel E. Artico M. Silvestri R. J. Med. Chem. 2006, 49: 947

<A NAME="RF10410SS-3">3</A> Kaldor SW. Kalish VJ. Davies JF. Shetty BV. Fritz JE. Appelt K. Burgess JA. Campanale KM. Chirgadze NY. Clawson DK. Dressman BA. Hatch SD. Khalil DA. Kosa MB. Lubbehusen PP. Muesing MA. Patick AK. Reich SH. Su KS. Tatlock JH. J. Med. Chem. 1997, 40: 3979

<A NAME="RF10410SS-4A">4a</A> Migita T. Shimizu T. Asami Y. Shiobara J. Kato Y. Kosugi M. Bull. Chem. Soc. Jpn. 1980, 53: 1385

<A NAME="RF10410SS-4B">4b</A> Kosugi M. Ogata T. Terada M. Sano H. Migita T. Bull. Chem. Soc. Jpn. 1985, 58: 3657

<A NAME="RF10410SS-5A">5a</A> Mann G. Baranano D. Hartwig JF. Rheingold AL. Guzei IA. J. Am. Chem. Soc. 1998, 120: 9205

<A NAME="RF10410SS-5B">5b</A> Li GY. Angew. Chem. Int. Ed. 2001, 40: 1513

<A NAME="RF10410SS-5C">5c</A> Itoh T. Mase T. Org. Lett. 2004, 6: 4587

<A NAME="RF10410SS-5D">5d</A> Fernandez-Rodriguez MA. Shen QL. Hartwig JF. J. Am. Chem. Soc. 2006, 128: 2180

<A NAME="RF10410SS-5E">5e</A> Fukuzawa S. Tanihara D. Kikuchi S. Synlett 2006, 2145

<A NAME="RF10410SS-5F">5f</A> Eichman CC. Stambuli JP. J. Org. Chem. 2009, 74: 4005

<A NAME="RF10410SS-5G">5g</A> Fernandez-Rodriguez MA. Hartwig JF. J. Org. Chem. 2009, 74: 1663

<A NAME="RF10410SS-6A">6a</A> Cristau HJ. Chabaud B. Chene A. Christol H. Synthesis 1981, 892

<A NAME="RF10410SS-6B">6b</A> Millois C. Diaz P. Org. Lett. 2000, 2: 1705

<A NAME="RF10410SS-6C">6c</A> Zhang YG. Ngeow KC. Ying JY. Org. Lett. 2007, 9: 3495

<A NAME="RF10410SS-6D">6d</A> Cao YQ. Zhang Z. Guo YX. Wu GQ. Synth. Commun. 2008, 38: 1325

<A NAME="RF10410SS-7">7</A> Wong YC. Jayanth TT. Cheng CH. Org. Lett. 2006, 8: 5613

<A NAME="RF10410SS-8A">8a</A> Kwong FY. Buchwald SL. Org. Lett. 2002, 4: 3517

<A NAME="RF10410SS-8B">8b</A> Wu YJ. He H. Synlett 2003, 1789

<A NAME="RF10410SS-8C">8c</A> Bates CG. Saejueng P. Doherty MQ. Venkataraman D. Org. Lett. 2004, 6: 5005

<A NAME="RF10410SS-8D">8d</A> Chen YJ. Chen HH. Org. Lett. 2006, 8: 5609

<A NAME="RF10410SS-8E">8e</A> Zhang H. Cao WG. Ma DW. Synth. Commun. 2007, 37: 25

<A NAME="RF10410SS-8F">8f</A> Sperotto E. van Klink GPM. de Vries JG. van Koten G. J. Org. Chem. 2008, 73: 5625

<A NAME="RF10410SS-9A">9a</A> Reddy VP. Kumar AV. Swapna K. Rao KR. Org. Lett. 2009, 11: 1697

<A NAME="RF10410SS-9B">9b</A> Reddy VP. Swapna K. Kumar AV. Rao KR. J. Org. Chem. 2009, 74: 3189

<A NAME="RF10410SS-10A">10a</A> Xu HJ. Zhao XY. Deng J. Fu Y. Feng YS. Tetrahedron Lett. 2009, 50: 434

<A NAME="RF10410SS-10B">10b</A> Prasad DJC. Naidu AB. Sekar G. Tetrahedron Lett. 2009, 50: 1411

<A NAME="RF10410SS-10C">10c</A> Ku X. Huang H. Jiang HL. Liu H. J. Comb. Chem. 2009, 11: 338

<A NAME="RF10410SS-10D">10d</A> Bhadra S. Sreedhar B. Ranu BC. Adv. Synth. Catal. 2009, 351: 2369

<A NAME="RF10410SS-10E">10e</A> Rout L. Sen TK. Punniyamurthy T. Angew. Chem. Int. Ed. 2007, 46: 5583

<A NAME="RF10410SS-10F">10f</A> Deng W. Zou Y. Wang YF. Liu L. Guo QX. Synlett 2004, 1254

<A NAME="RF10410SS-10G">10g</A> Jammi S. Sakthivel S. Rout L. Mukherjee T. Mandal S. Mitra R. Saha P. Punniyamurthy T. J. Org. Chem. 2009, 74: 1971

<A NAME="RF10410SS-10H">10h</A> Xu HJ. Zhao XY. Fu Y. Feng YS. Synlett 2008, 3063

<A NAME="RF10410SS-11">11</A> Herrero MT. SanMartin R. Dominguez E. Tetrahedron 2009, 65: 1500

<A NAME="RF10410SS-12">12</A> Feng Y. Wang HF. Sun FF. Li YM. Fu XM. Jin K. Tetrahedron 2009, 65: 9737

<A NAME="RF10410SS-13">13</A> Chakraborti AK. Sharma L. Nayak MK. J. Org. Chem. 2002, 67: 6406

<A NAME="RF10410SS-14">14</A> Akkilagunta VK. Reddy VP. Rao KR. Synlett 2010, 1260

<A NAME="RF10410SS-15A">15a</A> Goyot O. Gingras M. Tetrahedron Lett. 2009, 50: 1977

<A NAME="RF10410SS-15B">15b</A> Nakayama J. Katano N. Shimura Y. Sugihara Y. Ishii A. J. Org. Chem. 1996, 61: 7608

<A NAME="RF10410SS-16">16</A> Wang HF. Li YM. Sun FF. Feng Y. Jin K. Wang XN. J. Org. Chem. 2008, 73: 8639

<A NAME="RF10410SS-17">17</A> Bates CG. Gujadhur RK. Venkataraman D. Org. Lett. 2002, 4: 2803

<A NAME="RF10410SS-18">18</A> Marcincallefebvre A. Gesquiere JC. Lemer C. Dupuis B. J. Med. Chem. 1981, 24: 889

<A NAME="RF10410SS-19A">19a</A> Fernandez-Rodriguez MA. Shen QL. Hartwig JF. Chem. Eur. J. 2006, 12: 7782

<A NAME="RF10410SS-19B">19b</A> Sindelar K. Sedivy Z. Hrubantova M. Valchar M. Metysova J. Protiva M. Collect. Czech. Chem. Commun. 1988, 53: 381

<A NAME="RF10410SS-20">20</A> Lee JY. Lee PH. J. Org. Chem. 2008, 73: 7413

<A NAME="RF10410SS-21">21</A> Clark RD. Jahangir A. Severance D. Salazar R. Chang T. Chang D. Jett MF. Smith S. Bley K. Bioorg. Med. Chem. Lett. 2004, 14: 1053

<A NAME="RF10410SS-22">22</A> Allen JV. Bower JF. Williams JMJ. Tetrahedron: Asymmetry 1994, 5: 1895

<A NAME="RF10410SS-23">23</A> Vicente J. Abad JA. Lopez-Nicolas RM. Tetrahedron 2008, 64: 6281

<A NAME="RF10410SS-24">24</A> Bunnett JF. Creary X. J. Org. Chem. 1974, 39: 3611

<A NAME="RF10410SS-25A">25a</A> Kato T. Kuniyasu H. Kajiura T. Minami Y. Ohtaka A. Kinomoto M. Terao J. Kurosawa H. Kambe N. Chem. Commun. 2006, 868

<A NAME="RF10410SS-25B">25b</A> Bourgeois E. Fouassin A. Bull. Soc. Chim. Fr. 1911, 9: 941

<A NAME="RF10410SS-26A">26a</A> Petrillo G. Novi M. Garbarino G. Dellerba C. Tetrahedron 1986, 42: 4007

<A NAME="RF10410SS-26B">26b</A> Voronkov M. G. Deryagina E. N. Klochkova L. G. Ivanova G. M. Zh. Org. Khim. 1977, 13: 2575

Supplementary Material

Supporting Information