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Synthesis 2015; 47(08): 1101-1108
DOI: 10.1055/s-0034-1380129
DOI: 10.1055/s-0034-1380129
paper
Metal-Free Direct N-Benzylation of Sulfonamides with Benzyl Alcohols by Employing Boron Trifluoride–Diethyl Ether Complex
Further Information
Publication History
Received: 10 November 2014
Accepted after revision: 30 December 2014
Publication Date:
10 February 2015 (online)
Abstract
N-Benzylation of sulfonamides with both primary and secondary benzyl alcohols by employing boron trifluoride–diethyl ether complex under mild reaction conditions has been developed, which is an environmentally benign and facile protocol for assembling a series of primary and secondary benzyl sulfonamides in yields up to 83%. In this coupling reaction, the beneficial role of water has been clarified in detail through control experiments.
Key words
N-benzylation - sulfonamides - benzyl alcohols - boron trifluoride–diethyl ether complex - waterSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-34-1380129.
- Supporting Information
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References
- 1a Cole DC, Lennox WJ, Lombardi S, Ellingboe JW, Bernotas RC, Tawa GJ, Mazandarani H, Smith DL, Zhang G, Coupet J, Schechter LE. J. Med. Chem. 2005; 48: 353
- 1b Natarajan A, Guo Y, Harbinski F, Fan YH, Chen H, Luus L, Diercks J, Aktas H, Chorev M, Halperin JA. J. Med. Chem. 2004; 47: 4979
- 1c Banerjee M, Poddar A, Mitra G, Surolia A, Owa T, Bhattacharyya B. J. Med. Chem. 2005; 48: 547
- 2a Sridhar R, Srinivas B, Pavan Kumar V, Narender M, Rama Rao K. Adv. Synth. Catal. 2007; 349: 1873
- 2b Rattanaburi P, Khumraksa B, Pattarawarapan M. Tetrahedron Lett. 2012; 53: 2689
- 3a Yin JJ, Buchwald SL. J. Am. Chem. Soc. 2002; 124: 6043
- 3b Deng W, Liu L, Zhang C, Liu M, Guo QX. Tetrahedron Lett. 2005; 46: 7295
- 3c Burton G, Cao P, Li G, Rivero R. Org. Lett. 2003; 5: 4373
- 3d Steinhuebel D, Palucki M, Askin D, Dolling U. Tetrahedron Lett. 2004; 45: 3305
- 4a Xiao B, Gong TJ, Xu J, Liu ZJ, Liu L. J. Am. Chem. Soc. 2011; 133: 1466
- 4b Thu HY, Yu WY, Che CM. J. Am. Chem. Soc. 2006; 128: 9048
- 4c John A, Nicholas KM. J. Org. Chem. 2011; 76: 4158
- 4d Karshtedt D, Bell AT, Tilley TD. J. Am. Chem. Soc. 2005; 127: 12640
- 4e Zhang JL, Yang CG, He C. J. Am. Chem. Soc. 2006; 128: 1798
- 4f Caddick S, Wilden JD, Judd DB. J. Am. Chem. Soc. 2004; 126: 1024
- 4g Caddick S, Wilden JD, Bush HD, Wadman SN, Judd DB. Org. Lett. 2002; 4: 2549
- 5a Cui XJ, Zhang Y, Shi F, Deng YQ. Chem. Eur. J. 2011; 17: 1021
- 5b Liu CZ, Liao SH, Li Q, Feng SL, Sun Q, Yu XC, Xu Q. J. Org. Chem. 2011; 76: 5759
- 5c Feng SL, Liu CZ, Li Q, Yu XC, Xu Q. Chin. Chem. Lett. 2011; 22: 1021
- 6a Shi F, Tse MK, Zhou SL, Pohl MM, Radnik J, Hübner S, Jähnisch K, Brückner A, Beller M. J. Am. Chem. Soc. 2009; 131: 1775
- 6b Zhu MW, Fujita KI, Yamaguchi R. Org. Lett. 2010; 12: 1336
- 6c Li Q, Fan SJ, Sun Q, Tian HW, Yu XC, Xu Q. Org. Biomol. Chem. 2012; 10: 2966
- 6d Cui XJ, Shi F, Zhang Y, Deng YQ. Tetrahedron Lett. 2010; 51: 2048
- 7a Qin HB, Yamagiwa N, Matsunaga S, Shibasaki M. Angew. Chem. Int. Ed. 2007; 46: 409
- 7b Reddy CR, Madhavi PP, Reddy AS. Tetrahedron Lett. 2007; 48: 7169
- 7c Jana U, Maiti S, Biswas S. Tetrahedron Lett. 2008; 49: 858
- 7d Terrasson V, Marque S, Georgy M, Campagne JM, Prim D. Adv. Synth. Catal. 2006; 348: 2063
- 7e Sreedhar B, Reddy PS, Reddy MA, Neelima B, Arundhathi R. Tetrahedron Lett. 2007; 48: 8174
- 7f Sanz R, Martínez A, Álvarez-Gutiérrez JM, Rodríguez F. Eur. J. Org. Chem. 2006; 1383
- 7g Sanz R, Martínez A, Miguel D, Álvarez-Gutiérrez JM, Rodríguez F. Adv. Synth. Catal. 2006; 348: 1841
- 8a Chase PA, Jurca T, Stephan DW. Chem. Commun. 2008; 1701
- 8b Shaabani A, Soleimani E, Rezayan AH. Tetrahedron Lett. 2007; 48: 2185
- 9a Schäfer G, Bode JW. Angew. Chem. Int. Ed. 2011; 50: 10913
- 9b Xu XF, Xiong Y, Ling XG, Xie XM, Yuan J, Zhang ST, Song ZR. Chin. Chem. Lett. 2014; 25: 406
- 9c Fang ZX, Liu JQ, Liu Q, Bi XH. Angew. Chem. Int. Ed. 2014; 53: 7209
- 9d Onyango EO, Fu LF, Gribble GW. Org. Lett. 2014; 16: 322
- 9e Fang XQ, Liu K, Li CZ. J. Am. Chem. Soc. 2010; 132: 2274
- 9f Xiao DJ, Wang LJ, Feng XM. Synlett 2005; 1531
- 9g Shao LX, Zhang YP, Qi MH, Shi M. Org. Lett. 2007; 9: 117
- 9h Shi L, Tu YQ, Wang M, Zhang FM, Fan CA, Zhao YM, Xia WJ. J. Am. Chem. Soc. 2005; 127: 10836
- 10 Laubengayer AW, Finlay GR. J. Am. Chem. Soc. 1943; 65: 884
- 11a Prakash GK. S, Paknia F, Mathew T, Mlostoń G, Joschek JP, Olah GA. Org. Lett. 2011; 13: 4128
- 11b Prakash GK. S, Mathew T, Hoole D, Esteves PM, Wang Q, Rasul G, Olah GA. J. Am. Chem. Soc. 2004; 126: 15770
- 11c Prakash GK. S, Panja C, Shakhmin A, Shah E, Mathew T, Olah GA. J. Org. Chem. 2009; 74: 8659
- 11d Yu H, Li CZ. J. Org. Chem. 2004; 69: 142
- 11e Liu L, Wang X, Li CZ. Org. Lett. 2003; 5: 361
- 12a Li Y, Xiong Y, Li XM, Ling XG, Huang RF, Zhang XH, Yang JC. Green Chem. 2014; 16: 2976
- 12b Zhang ST, Zhang XH, Ling XG, He C, Huang RF, Pan J, Li JQ, Xiong Y. RSC Adv. 2014; 4: 30768
- 12c Huang RF, Zhang XH, Pan J, Li JQ, Shen H, Ling XG, Xiong Y. Tetrahedron 2015; in press; DOI: 10.1016/j.tet.2015.01.037