Towards the Preparation of Stable Cyclic Amino(ylide)Carbenes.

ABSTRACT: Cyclic amino(ylide)carbenes (CAYCs) are the ylide-substituted analogues of N-heterocyclic Carbenes (NHCs). Due to the stronger π donation of the ylide compared to an amino moiety they are stronger donors and thus are desirable ligands for catalysis. However, no stable CAYC has been reported until today. Here, we describe experimental and computational studies on the synthesis and stability of CAYCs based on pyrroles with trialkyl onium groups. Attempts to isolate two CAYCs with trialkyl phosphonium and sulfonium ylides resulted in the deprotonation of the alkyl groups instead of the formation of the desired CAYCs. In case of the PCy₃-substituted system, the corresponding ylide was isolated, while deprotonation of the SMe₂-functionalized compound led to the form

SUBMITTER: Steinert H 

PROVIDER: S-EPMC7070660 | biostudies-literature | 2020 Feb

REPOSITORIES: biostudies-literature