Annulative coupling of vinylboronic esters: aryne-triggered 1,2-metallate rearrangement

Haruki Mizoguchi, Hidetoshi Kamada, Kazuki Morimoto, Ryuji Yoshida, Akira Sakakura

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)

Abstract

A stereoselective annulative coupling of a vinylboronic ester ate-complex with arynes producing cyclic borinic esters has been developed. An annulation reaction that proceeded through the formation of two C-C bonds and a C-B bond was realized by exploiting a 1,2-metallate rearrangement of boronate triggered by the addition of a vinyl group to the strained triple bond of an aryne. The generated aryl anion would then cyclize to a boron atom to complete the annulation cascade. The annulated borinic ester could be converted to boronic acids and their derivatives by oxidation, halogenation, and cross-coupling. Particularly, halogenation and Suzuki-Miyaura coupling proceeded in a site-selective fashion and produced highly substituted alkylboronic acid derivatives.

Original languageEnglish
JournalChemical Science
DOIs
Publication statusAccepted/In press - 2022

ASJC Scopus subject areas

  • General Chemistry

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