Remote Nucleophilic Allylation by Allylrhodium Chain Walking

Chemistry : a European Journal
Alistair GrovesHon Wai Lam

Abstract

Metal migration through a carbon chain is a versatile method for achieving remote functionalization. However, almost all known examples involve the overall net migration of alkylmetal species. Here, we report that allylrhodium species obtained from hydrorhodation of 1,3-dienes undergo chain walking toward esters, amides, or (hetero)arenes over distances of up to eight methylene units. The final, more highly conjugated allylrhodium species undergo nucleophilic allylation with aldehydes and with an imine to give Z-homoallylic alcohols and amines, respectively.

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Citations

Jun 20, 2019·Angewandte Chemie·Christopher CoozeRylan J Lundgren
May 26, 2021·Journal of the American Chemical Society·Sinem GuvenFranziska Schoenebeck
Jul 14, 2021·Journal of the American Chemical Society·Christopher J C CoozeRylan J Lundgren

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