Decarboxylative alkenylation

Jacob T. Edwards, Rohan R. Merchant, Kyle S. McClymont, Kyle W. Knouse, Tian Qin, Lara R. Malins, Benjamin Vokits, Scott A. Shaw, Deng Hui Bao, Fu Liang Wei, Ting Zhou, Martin D. Eastgate, Phil S. Baran

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122 Scopus citations

Abstract

Olefin chemistry, through pericyclic reactions, polymerizations, oxidations, or reductions, has an essential role in the manipulation of organic matter. Despite its importance, olefin synthesis still relies largely on chemistry introduced more than three decades ago, with metathesis being the most recent addition. Here we describe a simple method of accessing olefins with any substitution pattern or geometry from one of the most ubiquitous and variegated building blocks of chemistry: alkyl carboxylic acids. The activating principles used in amide-bond synthesis can therefore be used, with nickel- or iron-based catalysis, to extract carbon dioxide from a carboxylic acid and economically replace it with an organozinc-derived olefin on a molar scale. We prepare more than 60 olefins across a range of substrate classes, and the ability to simplify retrosynthetic analysis is exemplified with the preparation of 16 different natural products across 10 different families.

Original languageEnglish (US)
Pages (from-to)213-218
Number of pages6
JournalNature
Volume545
Issue number7653
DOIs
Publication statusPublished - May 11 2017
Externally publishedYes

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Cite this

Edwards, J. T., Merchant, R. R., McClymont, K. S., Knouse, K. W., Qin, T., Malins, L. R., ... Baran, P. S. (2017). Decarboxylative alkenylation. Nature, 545(7653), 213-218. https://doi.org/10.1038/nature22307