Since their discovery in 2005, five-membered cyclic (alkyl)(amino)carbenes (CAAC-5) have found numerous applications ranging from the stabilization of highly reactive species to homogeneous catalysis and materials. Better s-donors and p-acceptors than the well-known N-heterocyclic carbenes (NHCs), these stable singlet carbenes have earned their growing popularity to the strong bonds they form with transition metals – this specificity which was shown to be critical for obtaining durable catalysts, and efficient OLEDs materials. To expand their scope further, we recently envisaged the preparation of CAACs bearing an ancillary functional group at nitrogen. Capitalizing on readily available pre-alkylated aldehydes, herein we wish to disclose the synthesis of CAACPhos, a new class of cyclic (alkyl)(amino)carbenes bearing an ancillary phosphine moiety. We will discuss their propensity to afford stable ylides as well as their electronic and structural properties as bidentate ligands for transition metal catalysis.

Convenient synthesis of a new bidentate cyclic(alkyl)(amino)carbene (CAACPhos)

ACS Spring 2022

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.