Synthesis of 3-trifluoromethylbenzo[b]furans from phenols via direct ortho functionalization by extended Pummerer reaction

Takayuki Kobatake; Daishi Fujino; Suguru Yoshida; Hideki Yorimitsu; Koichiro Oshima

doi:10.1021/ja1030134

Synthesis of 3-trifluoromethylbenzo[b]furans from phenols via direct ortho functionalization by extended Pummerer reaction

J Am Chem Soc. 2010 Sep 1;132(34):11838-40. doi: 10.1021/ja1030134.

Authors

Takayuki Kobatake¹, Daishi Fujino, Suguru Yoshida, Hideki Yorimitsu, Koichiro Oshima

Affiliation

¹ Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto-daigaku Katsura, Nishikyo-ku, Kyoto 615-8510, Japan.

PMID: 20687603
DOI: 10.1021/ja1030134

Abstract

A concise and diversity-oriented route to trifluoromethylbenzo[b]furans has been devised. A variety of phenols are directly converted to the corresponding 2-methylthio-3-trifluoromethylbenzo[b]furans by new triflic-anhydride-mediated extended Pummerer annulation reactions with trifluoromethylketene dithioacetal monoxide. The methylthio group of the products undergoes further transformations, which increase the diversity of available trifluoromethylbenzo[b]furans.

Publication types

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

MeSH terms

Benzofurans / chemical synthesis*
Benzofurans / chemistry
Cyclization
Molecular Structure
Phenols / chemistry*
Stereoisomerism

Substances

Benzofurans
Phenols