Metal-Free Direct Alkylation of Ketene Dithioacetals by Oxidative C(sp 2 )-H/C(sp 3 )-H Cross-Coupling.
CHEMISTRY-A EUROPEAN JOURNAL(2017)
摘要
The functionalization of internal olefins has been a challenging task in organic synthesis. This protocol provides an efficient and transition-metal-free direct oxidative C(sp(2))-H/C(sp(3))-H cross-coupling method to access tetrasubstituted olefins. The push-pull effect from the polarized olefin substrates accelerates the internal olefin C-H alkylation. Importantly, the mechanistic experimental results demonstrate that the alkanes C-H bond cleavage is the rate-determining step, and a radical pathway has been proposed for the alkylation reaction. Notably, the present protocol has excellent functional group tolerance and could be easily scaled up with good efficiency.
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关键词
alkylation,C-H activation,internal olefins,metal-free,cross-coupling
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