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Manganese(I)-Catalyzed Direct C–H Allylation of Arenes with Allenes

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journal contribution
posted on 26.09.2017, 00:00 authored by Shi-Yong Chen, Qingjiang Li, Honggen Wang
Polysubstituted allyl groups, for example, the prenyl group, are valuable synthetic handles and widely encountered in bioactive compounds. Reported herein is a manganese­(I)-catalyzed direct C–H coupling with allenes for the efficient assembly of allylated arenes. The protocol offers an extremely high level of atom-economy and is particularly suited for the introduction of 1,1-disubstitiuted allyl groups, as exemplified by the quantitative syntheses of a variety of prenylated indoles. The practicality of this method was evidenced by a gram-scale synthesis with a lower catalyst loading of manganese­(I) (2.5 mol %, 95% yield). Experimental mechanistic studies were conducted, and a possible reaction mechanism was proposed.