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J Org Chem. 2016 Mar 04;81(5):2113-21. doi: 10.1021/acs.joc.6b00137. Epub 2016 Feb 18.

Hypervalent Iodine as a Terminal Oxidant in Wacker-Type Oxidation of Terminal Olefins to Methyl Ketones.

The Journal of organic chemistry

Dipali A Chaudhari, Rodney A Fernandes

Affiliations

  1. Department of Chemistry, Indian Institute of Technology Bombay , Powai, Mumbai 400076, Maharashtra, India.

PMID: 26845633 DOI: 10.1021/acs.joc.6b00137

Abstract

A mimic of the Wacker process for C═O bond formation in terminal olefins can be initiated by a combination of the Pd(II) and hypervalent iodine reagent, Dess-Martin periodinane to generate methyl ketones. This operationally simple and scalable method offers Markovnikov selectivity, has good functional group compatibility, and is mild and high yielding.

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