Phosphaborenes: Accessible Reagents for the Synthesis of C-C/P-B Isosteres

Amy N Price; Gary S Nichol; Michael J Cowley

doi:10.1002/anie.201705050

Phosphaborenes: Accessible Reagents for the Synthesis of C-C/P-B Isosteres

Angew Chem Int Ed Engl. 2017 Aug 7;56(33):9953-9957. doi: 10.1002/anie.201705050. Epub 2017 Jul 19.

Authors

Amy N Price¹, Gary S Nichol¹, Michael J Cowley¹

Affiliation

¹ EaStCHEM, School of Chemistry, University of Edinburgh, Edinburgh, EH9 3FJ, UK.

PMID: 28643472
DOI: 10.1002/anie.201705050

Abstract

Formal exchange of C=C units with isoelectronic B=N or B=P units can provide access to molecules with unique electronic or chemical properties. Herein, we report the simple solution-phase generation of highly reactive phosphaborenes, RP=BR, and demonstrate their use for the introduction of P=B units into organic systems. Ring opening of a P-B-containing cyclobutene isostere provided access to unique 1,4-boraphosphabutadiene systems with conjugated main-group multiple bonds.

Keywords: boron; carbenes; conjugation; multiple bonds; phosphorus.

Publication types

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