Synthesis of 2-Alkynyltetrahydrofuran Derivatives from Tetrahydrofuran and Alkynyl Bromides

Abstract

An efficient and general method for the synthesis of 2-alkynyltetrahydrofuran was developed. The regioselective functionalization of the C(sp³)–H bond adjacent to an oxygen atom with various alkynyl bromides has been achieved under transition-metal-free reaction conditions. Sodium fluoride was found, for the first time, to promote the efficient functionalization process remarkably. Moreover, 1,2-dibromostyrenes were also found to be effective in this method forming 2-alkenyltetrahydrofurans.

Key words

2-alkynyltetrahydrofuran - tetrahydrofuran - alkynyl bromides - sodium fluoride - free radical

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