Litcius/Paper detail

Iron-Photocatalyzed Decarboxylative Alkylation of Carboxylic Acids with Morita–Baylis–Hillman Acetates

Yanli Yin, Fang Chen, Dong Chen, Peizhong Xie, Dongping Wang, Teck‐Peng Loh

2024Organic Letters21 citationsDOI

Abstract

We present an iron-photocatalyzed decarboxylative alkylation strategy involving carboxylic acids and Morita–Baylis–Hillman (MBH) acetates to synthesize E -type tri- and tetrasubstituted alkenes with moderate to excellent stereoselectivity ( E / Z ratio up to >19:1). This method is applicable to a broad range of structurally diverse primary, secondary, and tertiary alkyl carboxylic acids, as well as complex pharmaceutical and natural carboxylic acids, achieving efficient alkylation of various MBH acetates under mild conditions (>60 examples, with yields up to 96%). This approach offers a powerful strategy for streamlined alkylation.

Topics & Concepts

ChemistryAlkylationPrimary (astronomy)Organic chemistryAlkylCarboxylic acidStereoselectivityCatalysisPhysicsAstronomyRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques