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Pd-Catalyzed Dual-γ-1,1-C(sp<sup>3</sup>)−H Activation of Free Aliphatic Acids with Allyl−O Moieties
Journal
ACS Catalysis
Date Issued
2022-09-16
Author(s)
Das, Jayabrata
Pal, Tanay
Ali, Wajid
Sahoo, Sumeet Ranjan
Maiti, Debabrata
Abstract
Allyl alcohols represent a unique class of coupling partners in C−H functionalization reactions. In this work, we report a simple strategy that involves dual-1,1-C(sp3)−H activation of free aliphatic acids, leading to the direct synthesis of γ-lactones that contain α,β-unsaturated groups at the γ-position. Various allyl alcohols including primary, secondary, tertiary, etc., have been used as suitable coupling partners to generate a diverse range of γ-lactones. A number of aliphatic acids including the long-chain ones have been used as substrates in the protocol. A mechanistic investigation has been carried out and suggests C−H activation to be the rate-determining step and a subsequent allylic C−H activation in the reaction. The synthesized lactones having α,β-unsaturated fragments attached are expected to be useful in the synthesis of complex molecules via further synthetic manipulation.
Volume
12
Subjects