Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2015; 47(21): 3286-3291
DOI: 10.1055/s-0035-1560476
DOI: 10.1055/s-0035-1560476
feature
Base-Free Palladium-Catalyzed Cross-Coupling of Arylsulfonium Salts with Sodium Tetraarylborates
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.
Key words
C–S cleavage - C–C bond formation - cross-coupling - sulfonium salts - sodium tetraarylborates - palladiumSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1560476.
- 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
- 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
- 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
- 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
- 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
For examples of base-free reactions with other organoboron reagents, see:
For reviews on the cross-coupling of organosulfur compounds, see:
For pioneering work on the cross-coupling of organic sulfides, see:
For our work on the cross-coupling of aryl sulfides, see: