| Abstract
| - Kinetic vs thermodynamic deprotonation studies on secondary and tertiary sulfonamides 1 and 2using n-BuLi have been carried out. While both 1 and 2 show kinetic ortho-metalation,thermodynamic conditions lead to ortho and benzylic deprotonation, respectively (Figures and). Metalation of 1 using the n-BuLi/KOtBu superbase led to regioselective benzylic metalation(Figure ); LDA deprotonation was also briefly explored. Application of the developed conditionsallows the synthesis of diverse sulfonamide products 5a−e, 6a−e, 7a,b, and 8a−e. Ipso-bromodesilylation reactions afford sulfonamides 9a,b while Suzuki cross-coupling reactions furnish biarylsulfonamides 11a−c.
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