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Selective Ortho and Benzylic Functionalization of Secondary and Tertiary p-Tolylsulfonamides. Ipso-Bromo Desilylation and Suzuki Cross Coupling Reactions

Stephen L. MacNeil, O. B. Familoni, Victor Snieckus*

*Departement of Chemistry, Queen's University, Kingston, ON, Canada, K7L3N6, Email: snieckuschem.queensu.ca

S. L. MacNeil, O. B. Familoni, V. Snieckus, J. Org. Chem, 2001, 66, 3662-3670.

DOI: 10.1021/jo001402s (free Supporting Information)



 
E+
 
Yield (%, isol.)
 
MeI 92
PhCHO 93
I2 92

see article for more reactions

Abstract

Kinetic vs thermodynamic deprotonation studies on secondary and tertiary sulfonamides using n-BuLi have been carried out. Application of the developed conditions allows the synthesis of diverse sulfonamide products. Subsequent Suzuki cross-coupling reactions of iodo derivatives furnish various biaryl sulfonamides.

Boronic Acid
 
eq.
 
t (h)
 
Yield (%, isol.)
 
PhB(OH)2 2.2 24 95
3 26 92

see article for more reactions



Key Words

DoM, Directed Ortho Metalation, Suzuki Coupling, Iodination, Benzylic Alcohols


ID: J42-Y2001-020