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

Abstract

The interaction of carbon monoxide with an intramolecular FLP and a strong electrophile leads to rapid cleavage of the CO triple bond and enables the formation of new B/N heterocycles via selective incorporation of single carbon atoms.

Frustrated Lewis pair chemistry of CO

“…More recently, a 2021 report from Krempner and coworkers 20 described the remarkable reaction of the B/N FLP C 6 H 4 (9-BBN)(NC(NMe 2 ) 2 ) 8 with CO. While at room temperature this species captures CO to give 9 , at 120 °C the B and CO fragment swap places affording C 6 H 4 C(O)(9-BBN)(NC(NMe 2 ) 2 ) 10 (Scheme 2).…”

Understanding the CO capture reaction through electronic structure analysis of four-membered-ring group-13/N- and B/group-15-based Lewis acid–base pairs

“…Subsequently, relevant experimental results of CO being captured by different types of FLP-assisted molecules were reported successively. [37][38][39][40][41][42] However, theoretical study on the capture reaction of CO by FLP-related molecules is comparatively rare. 43 Thus, the bonding nature and related information concerning CO sequestration by FLPs remain rather poorly understood.…”

Intramolecular frustrated Lewis pair mediated approach to the CO bond activation and cleavage of carbon dioxide

“…At the outset, we investigated the ability of FLP 1 9 to sequester CO 2 . In fact, upon exposure of CO 2 (2 bar) to a hexane solution of 1 , a crystalline material precipitated, which was identified by multi-nuclear NMR and IR spectroscopy as FLP-CO 2 adduct 2 (93%) (Fig.…”