Borylative cyclisation of diynes using BCl3 and borocations

Andrew J. Warner, Kieron M. Enright, John M. Cole, Kang Yuan, John S. Mcgough, Michael J. Ingleson

Research output: Contribution to journalArticlepeer-review

Abstract

The borylative cyclisation of 1,2-dialkynyl benzenes with BCl3 leads to dibenzopentalenes (via intramolecular SEAr) or benzofulvenes (via chloride addition) depending on substituents, with stabilised vinyl cation intermediates (e.g. with a p-MeO-C6H4-group) favouring the latter. The use of borocations leads to more selective dibenzopentalene formation, while other diyne frameworks undergo intramolecular SEAr selectively even with p-MeO groups.
Original languageEnglish
JournalOrganic & Biomolecular chemistry
Early online date20 May 2019
DOIs
Publication statusE-pub ahead of print - 20 May 2019

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