Cremlyn, Richard; Swinbourne, Frederick J.; Graham, Stephen, Phosphorus, Sulfur and Silicon and the Related Elements, 1990, vol. 53, # 1-4, p. 121 - 134
Selective <i>Ortho</i> and Benzylic Functionalization of Secondary and Tertiary <i>p</i>-Tolylsulfonamides. <i>Ipso</i>-Bromo Desilylation and Suzuki Cross-Coupling Reactions
作者:Stephen L. MacNeil、O. B. Familoni、Victor Snieckus
DOI:10.1021/jo001402s
日期:2001.6.1
Kinetic vs thermodynamic deprotonation studies on secondary and tertiary sulfonamides 1 and 2 using 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 1 and 2). Metalation of 1 using the n-BuLi/KOtBu superbase led to regioselective benzylic metalation (Figure 4); LDA deprotonation was