Characterization of the zwitterionic intermediate in 1,1‐carboboration of alkynes

Alessandro Bismuto, Gary S. Nichol, Fernanda Duarte, Michael J. Cowley, Stephen Thomas

Research output: Contribution to journalArticlepeer-review

Abstract

The reaction of a Lewis acidic borane with an alkyne is a key step in a diverse range of main group transformations. Alkyne 1,1‐carboboration, the Wrackmeyer reaction, is an archetypal transformation of this kind. 1,1‐Carboboration has been proposed to proceed through a zwitterionic intermediate. We report the isolation and spectroscopic, structural and computational characterization of the zwitterionic intermediates generated by reaction of B(C6F5)3 with alkynes. The stepwise reactivity of the zwitterion provides new mechanistic insight for 1,1‐carboboration and wider B(C6F5)3 catalysis. Making use of intramolecular stabilization by a ferrocene substituent, we have characterized the zwitterionic intermediate in the solid state and diverted reactivity towards alkyne cyclotrimerization.
Original languageEnglish
Pages (from-to)12731-12735
Number of pages5
JournalAngewandte Chemie International Edition
Volume59
Issue number31
Early online date29 May 2020
DOIs
Publication statusPublished - 27 Jul 2020

Fingerprint Dive into the research topics of 'Characterization of the zwitterionic intermediate in 1,1‐carboboration of alkynes'. Together they form a unique fingerprint.

Cite this