Carbon monoxide bond cleavage mediated by an intramolecular frustrated Lewis pair: access to new B/N heterocycles via selective incorporation of single carbon atoms

Chamila P Manankandayalage; Daniel K Unruh; Clemens Krempner

doi:10.1039/d1cc05673e

Carbon monoxide bond cleavage mediated by an intramolecular frustrated Lewis pair: access to new B/N heterocycles via selective incorporation of single carbon atoms

Chem Commun (Camb). 2021 Nov 23;57(93):12528-12531. doi: 10.1039/d1cc05673e.

Authors

Chamila P Manankandayalage¹, Daniel K Unruh¹, Clemens Krempner¹

Affiliation

¹ Department of Chemistry and Biochemistry, Texas Tech University, Memorial Dr & Boston, Lubbock, TX, 79409, USA. clemens.krempner@ttu.edu.

PMID: 34766617
DOI: 10.1039/d1cc05673e

Abstract

Utilizing an intramolecular frustrated Lewis pair (FLP) decorated with a strongly donating guanidino moiety enabled the formation of a thermally remarkably stable FLP-CO adduct, which at 120 °C underwent CO migration to form an acyl borane. Both compounds underwent rapid CO cleavage in the presence of strong electrophiles leading to the selective formation of a range of new 1,2- and 1,3-benzazaboroles in good yields under mild conditions.