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Paper | Special issue | Vol 95, No. 1, 2017, pp.474-486
Published online, 20th January, 2017
DOI: 10.3987/COM-16-S(S)38
A Direct Synthesis of 2,2-Disubstituted 3-Silylchromenes by [4+2] Cycloaddition of in situ Generated o-Quinonemethides with Electron-Rich Alkynes

Kenta Tanaka, Yujiro Hoshino, and Kiyoshi Honda*

*Graduate School of Environment and Infomation Science, Yokohama National University, Tokiwadai, Hodogaya-ku, Yokohama 240-8501, Japan

Abstract

A direct synthesis of 2,2-disubstituted 3-silylchromenes by [4+2] cycloaddition of in situ generated o-quinonemethides with electron-rich alkynes has been developed. The procedure is applicable for easily available starting materials like various substituted alkynylsilanes and salicylaldehydes. The present reaction provides versatile access to functionalized 2H-chromenes that would be a useful tool for the synthesis of biologically and photochemically active molecules.