Iron-catalyzed cascade carbochloromethylation of activated alkenes: highly efficient access to chloro-containing oxindoles

Ming-Zhu Lu; Teck-Peng Loh

doi:10.1021/ol502411c

Iron-catalyzed cascade carbochloromethylation of activated alkenes: highly efficient access to chloro-containing oxindoles

Org Lett. 2014 Sep 19;16(18):4698-701. doi: 10.1021/ol502411c. Epub 2014 Sep 9.

Authors

Ming-Zhu Lu¹, Teck-Peng Loh

Affiliation

¹ Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China , Hefei, 230026, China.

PMID: 25203302
DOI: 10.1021/ol502411c

Abstract

An iron-catalyzed carbodi- and trichloromethylation of activated alkenes with readily available dichloro- and tetrachloromethane has been developed. A diaryliodonium salt is used as an efficient oxidant in this transformation. This reaction tolerates a variety of functional groups and allows for a highly efficient synthesis of various chloro-containing oxindoles.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkenes / chemistry*
Carbon Tetrachloride / chemistry
Catalysis
Ferrous Compounds / chemistry*
Hydrocarbons, Chlorinated / chemical synthesis*
Hydrocarbons, Chlorinated / chemistry
Indoles / chemical synthesis*
Indoles / chemistry
Methylene Chloride / chemistry
Molecular Structure
Oxidants / chemistry
Oxindoles

Substances

Alkenes
Ferrous Compounds
Hydrocarbons, Chlorinated
Indoles
Oxidants
Oxindoles
2-oxindole
Methylene Chloride
Carbon Tetrachloride
ferrous chloride