Generation of Arynes via Ate Complexes of Arylboronic Esters with an ortho-Leaving Group

An efficient method of generating aryne has been achieved by treating ortho-(trifluoromethanesulfonyloxy)arylboronic acid pinacol ester with tert- or sec-butyllithium. Monitoring the reaction by 11B NMR has indicated that a boron-ate complex formed in situ is the eventual precursor that converts int...

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Bibliographic Details
Published in:Organic letters 2013-06, Vol.15 (11), p.2806-2809
Main Authors: Sumida, Yuto, Kato, Tomoe, Hosoya, Takamitsu
Format: Article
Language:English
Subjects:
Boronic Acids - chemistry
Butanones - chemistry
Catalysis
Esters
Lithium Compounds - chemistry
Magnetic Resonance Spectroscopy
Molecular Structure
Stereoisomerism
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Summary:An efficient method of generating aryne has been achieved by treating ortho-(trifluoromethanesulfonyloxy)arylboronic acid pinacol ester with tert- or sec-butyllithium. Monitoring the reaction by 11B NMR has indicated that a boron-ate complex formed in situ is the eventual precursor that converts into aryne near room temperature. The prior formation of the ate complex at a low temperature has enabled us to use various arynophiles, including those bearing base-sensitive groups. The ready availability of the aryne precursors and mutual orthogonality in aryne generation with widely used ortho-silylaryl triflate have enhanced the utility of the method.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol401140d