Chemistry - A European Journal
Chemistry - A European Journal
5 years ago

Metal-Free Direct Alkylation of Ketene Dithioacetals by Oxidative C(sp2)−H/C(sp3)−H Cross-Coupling

Metal-Free Direct Alkylation of Ketene Dithioacetals by Oxidative C(sp2)−H/C(sp3)−H Cross-Coupling
Aiwen Lei, Fan Zhang, Wenyan Shi, Jiangwei Wen
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(sp2)−H/C(sp3)−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. A bond-cleavage without metals: This protocol provides an efficient and conventional method to obtain tetrasubstituted olefins. Importantly, the results of mechanistic experiments demonstrate that the alkane C−H bond cleavage is involved in the rate-determining step, and a radical pathway is proposed for the alkylation reaction. Notably, the present protocol has excellent functional group tolerance and could be easily scaled up with good efficiency.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/chem.201701664

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