Synthesis, characterisation and reactions of phosphine-substituted alkynylboronates and alkynyltrifluoroborate salts

Jérôme F Vivat; Sylvestre P J T Bachollet; Harry Adams; Joseph P A Harrity

doi:10.3390/molecules191221324

Synthesis, characterisation and reactions of phosphine-substituted alkynylboronates and alkynyltrifluoroborate salts

Molecules. 2014 Dec 18;19(12):21324-34. doi: 10.3390/molecules191221324.

Authors

Jérôme F Vivat¹, Sylvestre P J T Bachollet², Harry Adams³, Joseph P A Harrity⁴

Affiliations

¹ Department of Chemistry, University of Sheffield, Sheffield S3 7HF, UK. vivat.jerome@gmail.com.
² Department of Chemistry, University of Sheffield, Sheffield S3 7HF, UK. s.bachollet@sheffield.ac.uk.
³ Department of Chemistry, University of Sheffield, Sheffield S3 7HF, UK. h.adams@shef.ac.uk.
⁴ Department of Chemistry, University of Sheffield, Sheffield S3 7HF, UK. j.harrity@sheffield.ac.uk.

Abstract

The synthesis and structural characterisation of phosphine-substituted alkynylboronates is reported. A P(III)-centred alkynylboronate (2) was prepared that showed little evidence for the conjugation of the P-lone pair to the boron via the alkyne π-system, as judged by X-ray crystallography studies of 2 and a related P(V) compound, 3. In addition, corresponding alkynyltrifluoroborate salts were prepared that showed improved stability by comparison to their boronic ester counterparts. These salts undergo Pd-catalysed cross-coupling reactions with aryl halides.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Boronic Acids / chemical synthesis*
Crystallography, X-Ray
Phosphines / chemical synthesis*
Salts

Substances

Boronic Acids
Phosphines
Salts