Distal γ-C(sp )-H Olefination of Ketone Derivatives and Free Carboxylic Acids.

Angew Chem Int Ed Engl

Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA, 92037, USA.

Published: July 2020

Reported herein is the distal γ-C(sp )-H olefination of ketone derivatives and free carboxylic acids. Fine tuning of a previously reported imino-acid directing group and using the ligand combination of a mono-N-protected amino acid (MPAA) and an electron-deficient 2-pyridone were critical for the γ-C(sp )-H olefination of ketone substrates. In addition, MPAAs enabled the γ-C(sp )-H olefination of free carboxylic acids to form diverse six-membered lactones. Besides alkyl carboxylic acids, benzylic C(sp )-H bonds also could be functionalized to form 3,4-dihydroisocoumarin structures in a single step from 2-methyl benzoic acid derivatives. The utility of these protocols was demonstrated in large scale reactions and diversification of the γ-C(sp )-H olefinated products.

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Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7494175PMC
http://dx.doi.org/10.1002/anie.202003271DOI Listing

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