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: snieckus
chem.queensu.ca
S. L. MacNeil, O. B. Familoni, V. Snieckus, J. Org. Chem, 2001, 66, 3662-3670.
DOI: 10.1021/jo001402s (free Supporting Information)
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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 |
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Key Words
DoM, Directed Ortho Metalation, Suzuki Coupling, Iodination, Benzylic Alcohols
ID: J42-Y2001-020
