Synthesis of N-alkylsulfonamides by borane–dimethyl sulfide reduction of N-acylsulfonamides
作者： Samantha N. James , Mark J. Coster
DOI: 10.1016/J.TETLET.2015.03.008
关键词:
摘要: Abstract A convenient synthesis of N-alkylsulfonamides in good to excellent yields by reduction N-acylsulfonamides using BH3·SMe2 is described. This methodology presents an attractive alternative for sulfonamide formation.
core.ac.uk
sci-hub.se 参考文章(19)
Jerry March, Advanced Organic Chemistry: Reactions, Mechanisms, and Structure ,(1977)
Peter G. M. Wuts, Theodora W. Greene, Protective groups in organic synthesis ,(1981)
Cihangir Tanyeli, Serhat Odabaş, Mine Erdem, Esen Çakır, Eda Keskin, Asymmetric synthesis of novel 1,4-aminoalcohol ligands with norbornene and norbornane backbone: use in the asymmetric diethylzinc addition to benzaldehyde Tetrahedron-asymmetry. ,vol. 18, pp. 2349- 2357 ,(2007) , 10.1016/J.TETASY.2007.09.019
Matthew H. Yates, Neil J. Kallman, Christopher P. Ley, Jeffrey N. Wei, Development of an Acyl Sulfonamide Anti-Proliferative Agent, LY573636·Na† Organic Process Research & Development. ,vol. 13, pp. 255- 262 ,(2009) , 10.1021/OP800210X
Oscar Lozano, George Blessley, Teresa Martinez del Campo, Amber L. Thompson, Guy T. Giuffredi, Michela Bettati, Matthew Walker, Richard Borman, Véronique Gouverneur, Organocatalyzed Enantioselective Fluorocyclizations Angewandte Chemie. ,vol. 50, pp. 8105- 8109 ,(2011) , 10.1002/ANIE.201103151
Kiumars Bahrami, Mohammad M. Khodaei, Jamshid Abbasi, Synthesis of sulfonamides and sulfonic esters via reaction of amines and phenols with thiols using H2O2–POCl3 system Tetrahedron. ,vol. 68, pp. 5095- 5101 ,(2012) , 10.1016/J.TET.2012.04.040
J. L. Belletire, D. F. Fry, A Useful Approach to Primary Amines Synthetic Communications. ,vol. 18, pp. 29- 35 ,(1988) , 10.1080/00397918808057816
S. K. GUPTA, New Reactions and Reagents; VI.1. A Simple Synthesis of N,N-Dialkylsulfonamides via the Reaction of Dialkylsulfamyl Chlorides with Aromatic Hydrocarbons Synthesis. ,vol. 1977, pp. 39- 41 ,(1977) , 10.1055/S-1977-24267
Hua Yang, Subham Mahapatra, Paul Ha-Yeon Cheong, Rich G. Carter, Highly Stereoselective and Scalable anti-Aldol Reactions using N-(p-dodecylphenylsulfonyl)-2-Pyrrolidinecarboxamide: Scope and Origins of Stereoselectivities Journal of Organic Chemistry. ,vol. 75, pp. 7279- 7290 ,(2010) , 10.1021/JO1015008
Stephen Caddick, Jonathan D. Wilden, Hannah D. Bush, Sjoerd N. Wadman, Duncan B. Judd, A new route to sulfonamides via intermolecular radical addition to pentafluorophenyl vinylsulfonate and subsequent aminolysis. Organic Letters. ,vol. 4, pp. 2549- 2551 ,(2002) , 10.1021/OL026181M