Au(III)/TPPMS-catalyzed benzylation of indoles with benzylic alcohols in water

Hidemasa Hikawa; Hideharu Suzuki; Isao Azumaya

doi:10.1021/jo402151g

Au(III)/TPPMS-catalyzed benzylation of indoles with benzylic alcohols in water

J Org Chem. 2013 Dec 6;78(23):12128-35. doi: 10.1021/jo402151g. Epub 2013 Nov 22.

Authors

Hidemasa Hikawa¹, Hideharu Suzuki, Isao Azumaya

Affiliation

¹ Faculty of Pharmaceutical Sciences, Toho University , 2-2-1, Miyama, Funabashi, Chiba 274-8510, Japan.

PMID: 24256426
DOI: 10.1021/jo402151g

Abstract

A novel and efficient method for the Au(III)/TPPMS-catalyzed direct substitution reaction of benzhydryl and benzylic alcohols with indoles in water is developed. Au(III)/TPPMS is an effective catalyst for the benzylation of the strong π nucleophile 1-methylindole, while common Brønsted or Lewis acids are ineffective.

Publication types

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

MeSH terms

Benzyl Alcohols / chemistry*
Catalysis
Gold / chemistry*
Indoles / chemistry*
Molecular Structure
Organophosphorus Compounds / chemistry*
Sulfonic Acids / chemistry*
Water / chemistry*

Substances

Benzyl Alcohols
Indoles
Organophosphorus Compounds
Sulfonic Acids
Water
Gold