Addition of benzyl ethers to alkynes: A metal-free synthesis of 1: H -isochromenes

Tzu Hsuan Kuan, Trimurtulu Kotipalli, Cheng Chun Chen, Duen Ren Hou

Research output: Contribution to journalArticlepeer-review

Abstract

Bromotrimethylsilane (TMSBr)-promoted intramolecular cyclization of (o-arylethynyl)benzyl ethers to form 1H-isochromenes at room temperature is reported. Further studies indicated that vinyl carbocations are the reaction intermediates which are stabilized by the conjugated aryl groups. Thus, O-addition of benzyl ethers/tetrahydropyrans to alkynes was achieved under metal-free, acidic conditions. These reaction conditions were compatible with an alkynyl Prins reaction; therefore, 1H-isochromenes were produced directly from alkynyl benzaldehydes and alkynyl alcohols using a one-pot procedure. This journal is

Original languageEnglish
Pages (from-to)10390-10402
Number of pages13
JournalOrganic and Biomolecular Chemistry
Volume19
Issue number47
DOIs
StatePublished - 21 Dec 2021

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