Chelate restrained boron cations for intermolecular electrophilic arene borylation

Alessandro Del Grosso, Robin G. Pritchard, Chris A. Muryn, Michael J. Ingleson

Research output: Contribution to journalArticlepeer-review

Abstract

Highly electrophilic boron species that borylate arenes are generated by halide abstraction from CatBX (Cat = catecholato, C6H 4O22-, X = Cl or Br) by [Et3Si] [CbBr6] (CbBr6 = [closo-1-H-CB11H 5Br6]-). A transient [CatB][CbBr6] related species reacts as a synthetic equivalent of [CatB]+ in intermolecular electrophilic borylation, with reactions proceeding rapidly at 25 °C. The [CatB]+ moiety was shown to be strongly Lewis acidic on the basis of 1H and 31P{1H} NMR spectroscopy of the crotonaldehyde and triethylphosphine oxide adducts, respectively. Catalytic quantities of [Et3Si][CbBr6] and CatBX were effective for the high-yielding borylation of arenes by CatBH in a highly atom efficient cycle with H2 the only byproduct. Successful catalysis was dependent on the robust [CbBr6]- anion and the use of electrophile-resistant borane sources

Original languageEnglish
Pages (from-to)241-249
Number of pages9
JournalOrganometallics
Volume29
Issue number1
DOIs
Publication statusPublished - 11 Jan 2010

Fingerprint

Dive into the research topics of 'Chelate restrained boron cations for intermolecular electrophilic arene borylation'. Together they form a unique fingerprint.

Cite this