Iron catalyzed methylation and ethylation of vinyl arenes.

Abstract

Short alkyl chain Heck (type) reactions, especially methyl Heck reactions, are a difficult aspect of the alkyl Heck reaction. To provide a solution to this problem, iron-catalyzed methyl, ethyl and propyl Heck reactions were developed using readily available alkyl peroxides as alkyl sources. The reaction conditions were mild, clean, and easy to handle. No additive was needed, and no hazardous waste was generated. The products were obtained in up to 99% yield of one isomer for most situations. This reaction works for many types of olefin and tolerates a variety of functional groups. Several late-stage functionalizations of natural products and drug molecules were conducted to demonstrate the synthetic applications of this reaction.