Synthesis 2015; 47(21): 3286-3291
DOI: 10.1055/s-0035-1560476
feature
© Georg Thieme Verlag Stuttgart · New York

Base-Free Palladium-Catalyzed Cross-Coupling of Arylsulfonium Salts with Sodium Tetraarylborates

Dhananjayan Vasu
a  Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto 606-8502, Japan   Email: yori@kuchem.kyoto-u.ac.jp
,
Hideki Yorimitsu*
a  Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto 606-8502, Japan   Email: yori@kuchem.kyoto-u.ac.jp
b  ACT-C, JST, Sakyo-ku, Kyoto 606-8502, Japan
,
Atsuhiro Osuka
a  Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto 606-8502, Japan   Email: yori@kuchem.kyoto-u.ac.jp
› Author Affiliations
Further Information

Publication History

Received: 12 July 2015

Accepted after revision: 24 August 2015

Publication Date:
08 September 2015 (online)


Abstract

Palladium-catalyzed cross-coupling reactions of arylsulfonium salts with sodium tetraarylborates were found to proceed smoothly without recourse to an additional base, providing a new, reliable route to biaryls from organosulfur compounds.

Supporting Information

 
  • References

    • 1a Miyaura N, Suzuki A. Chem. Rev. 1995; 95: 2457
    • 1b Suzuki A. J. Organomet. Chem. 1999; 576: 147
    • 1c Miyaura N. J. Organomet. Chem. 2002; 653: 54
    • 1d Suzuki A. Angew. Chem. Int. Ed. 2011; 50: 6723
    • 1e Chemler SR, Trauner D, Danishefsky SJ. Angew. Chem. Int. Ed. 2001; 40: 4544
    • 1f Nicolaou KC, Bulger PG, Sarlah D. Angew. Chem. Int. Ed. 2005; 44: 4442
    • 1g Suzuki A, Yamamoto Y. Chem. Lett. 2011; 40: 894
    • 2a Braga AA. C, Morgon NH, Ujaque G, Maseras F. J. Am. Chem. Soc. 2005; 127: 9298
    • 2b Lennox AJ. J, Lloyd-Jones GC. Angew. Chem. Int. Ed. 2013; 52: 7362
  • 3 Vasu D, Yorimitsu H, Osuka A. Angew. Chem. Int. Ed. 2015; 54: 7162
    • 4a Kurosawa H, Ogoshi S, Kawasaki Y, Murai S, Miyoshi M, Ikeda I. J. Am. Chem. Soc. 1990; 112: 2813
    • 4b Legros J.-Y, Fiaud J.-C. Tetrahedron Lett. 1990; 31: 7453
    • 4c Catellani M, Chiusoli GP, Vilma F. Gazz. Chim. Ital. 1990; 120: 779
    • 4d Ciattini PG, Morera E, Ortar G. Tetrahedron Lett. 1992; 33: 4815
    • 4e Yan J, Zhou Z, Zhu M. Tetrahedron Lett. 2005; 46: 8173
    • 4f Yan J, Zhou Z, Zhu M. Synth. Commun. 2006; 36: 1495
    • 4g Yan J, Zhu M, Zhou Z. Eur. J. Org. Chem. 2006; 2060
    • 4h Basu B, Das S, Kundu S, Mandal B. Synlett 2008; 255
    • 4i Yamada YM. A, Watanabe T, Beppu T, Fukuyama N, Torii K, Uozumi Y. Chem. Eur. J. 2010; 16: 11311

      For examples of base-free reactions with other organoboron reagents, see:
    • 5a Kabalka GW, Zhou L.-L, Naravane A. Tetrahedron Lett. 2006; 47: 6887
    • 5b Ohashi M, Saijo H, Shibata M, Ogoshi S. Eur. J. Org. Chem. 2013; 443
    • 5c Bjerglund KM, Skrydstrup T, Molander GA. Org. Lett. 2014; 16: 1888
    • 5d Mo F, Qiu D, Jiang Y, Zhang Y, Wang J. Tetrahedron Lett. 2011; 52: 518
    • 5e Emmanuvel L, Sudalai A. ARKIVOC 2007; (xiv): 126
    • 5f Yasuike S, Qin W, Sugawara Y, Kurita J. Tetrahedron Lett. 2007; 48: 721
    • 5g Ohmura T, Oshima K, Suginome M. Organometallics 2013; 32: 2870

      For reviews on the cross-coupling of organosulfur compounds, see:
    • 6a Dubbaka SR, Vogel P. Angew. Chem. Int. Ed. 2005; 44: 7674
    • 6b Prokopcová H, Kappe CO. Angew. Chem. Int. Ed. 2008; 47: 3674
    • 6c Wang L, He W, Yu Z. Chem. Soc. Rev. 2013; 42: 599
    • 6d Modha SG, Mehta VP, Van der Eycken EV. Chem. Soc. Rev. 2013; 42: 5042
    • 6e Pan F, Shi Z.-J. ACS Catal. 2014; 4: 280
    • 6f Garnier-Amblard EC, Liebeskind LS. Boronic Acids . 2nd ed.; Hall DG. Wiley-VCH; Weinheim: 2011: Chap. 7
    • 6g Zapf A. Angew. Chem. Int. Ed. 2003; 42: 5394

      For pioneering work on the cross-coupling of organic sulfides, see:
    • 7a Wenkert E, Ferreira TW, Michelotti EL. J. Chem. Soc., Chem. Commun. 1979; 637
    • 7b Okamura H, Miura M, Takei H. Tetrahedron Lett. 1979; 43

      For our work on the cross-coupling of aryl sulfides, see:
    • 8a Ookubo Y, Wakamiya A, Yorimitsu H, Osuka A. Chem. Eur. J. 2012; 18: 12690
    • 8b Murakami K, Yorimitsu H, Osuka A. Angew. Chem. Int. Ed. 2014; 53: 7510
    • 8c Sugahara T, Murakami K, Yorimitsu H, Osuka A. Angew. Chem. Int. Ed. 2014; 53: 9329
    • 8d Otsuka S, Fujino D, Murakami K, Yorimitsu H, Osuka A. Chem. Eur. J. 2014; 20: 13146
    • 8e Murakami K, Yorimitsu H, Osuka A. Bull. Chem. Soc. Jpn. 2014; 87: 1349
    • 8f Baralle A, Otsuka S, Guérin V, Murakami K, Yorimitsu H, Osuka A. Synlett 2015; 26: 327
    • 9a Srogl J, Allred GD, Liebeskind LS. J. Am. Chem. Soc. 1997; 119: 12376
    • 9b Zhang S, Marshall D, Liebeskind LS. J. Org. Chem. 1999; 64: 2796
    • 9c Lin H, Dong X, Li Y, Shen Q, Lu L. Eur. J. Org. Chem. 2012; 4675
    • 10a Abou A, Foubelo F, Yus M. ARKIVOC 2007; (v): 191
    • 10b Torii S, Matsuyama Y, Kawasaki K, Uneyama K. Bull. Chem. Soc. Jpn. 1973; 46: 2912
    • 11a Ōki M, Yamada Y, Murata S. Bull. Chem. Soc. Jpn. 1988; 61: 707
    • 11b Acheson RM, Harrison DR. J. Chem. Soc. C 1970; 1764
    • 11c Ohara Y, Akiba K.-Y, Inamoto N. Bull. Chem. Soc. Jpn. 1983; 56: 1508
    • 11d Laali KK, Chun J.-H, Okazaki T, Kumar S, Borosky GL, Swartz C. J. Org. Chem. 2007; 72: 8383
    • 12a Matsumoto M, Yoshioka H, Nakatsu K, Yoshida T, Otsuka S. J. Am. Chem. Soc. 1974; 96: 3322
    • 12b Littke AF, Dai C, Fu GC. J. Am. Chem. Soc. 2000; 122: 4020
    • 12c Dai C, Fu GC. J. Am. Chem. Soc. 2001; 123: 2719
  • 13 Barder TE, Buchwald SL. Org. Lett. 2004; 6: 2649
    • 14a Nishide K, Ohsugi S, Fudesaka M, Kodama S, Node M. Tetrahedron Lett. 2002; 43: 5177
    • 14b Ohsugi S, Nishide K, Oono K, Okuyama K, Fudesaka M, Kodama S, Node M. Tetrahedron 2003; 59: 8393
    • 14c Nishide K, Ohsugi S, Miyamoto T, Kumar K, Node M. Monatsh. Chem. 2004; 135: 189
    • 14d Nishide K, Node M. J. Synth. Org. Chem., Jpn. 2004; 62: 895
  • 15 Zhou W.-J, Wang K.-H, Wang J.-X, Gao Z.-R. Tetrahedron 2010; 66: 7633
    • 16a Pattanayak P, Parua SP, Patra D, Lai C.-K, Brandão P, Felix V, Chattopadhyay S. Inorg. Chim. Acta 2015; 429: 122
    • 16b Fodor A, Magyar Á, Barczikai D, Pirault-Roy L, Hell Z. Catal. Lett. 2015; 145: 834
    • 16c Nadri S, Rafiee E, Jamali S, Joshaghani M. Synlett 2015; 26: 619
    • 16d Chen L, Gao Z, Li Y. Catal. Today 2015; 245: 122
    • 16e Gartia Y, Ramidi P, Cheerla S, Felton CM, Jones DE, Das BC, Ghosh A. J. Mol. Catal. A: Chem. 2014; 392: 253
    • 16f Wu Y, Choy P.-Y, Kwong F.-K. Org. Biomol. Chem. 2014; 12: 6820
    • 16g Ghosh K, Iqubal MA, Molla RA, Mishra A, Kamaluddin, Islam SM. Catal. Sci. Technol. 2015; 5: 1606
    • 16h Hornillos V, Giannerini M, Vila C, Fañanás-Mastral M, Feringa BL. Org. Lett. 2013; 15: 5114
    • 16i Ma X, Liu Y, Liu P, Xie J, Dai B, Liu Z. Appl. Organomet. Chem. 2013; 27: 707