Crystalline BP-Doped Phenanthryne via Photolysis of The Elusive Boraphosphaketene

Yang, W.; Krantz, K. E.; Dickie, D. A.; Molino, A.; Wilson, D. J. D.; Gilliard Jr., R. J. Crystalline BP-Doped Phenanthryne via Photolysis of The Elusive Boraphosphaketene. Angewandte Chemie International Edition 2020, 59, 3850-3854.

NOTES

Yang, WenlongKrantz, Kelsie EDickie, Diane AMolino, AndrewWilson, David J DGilliard, Robert J JrengUniversity of VirginiaGermanyAngew Chem Int Ed Engl. 2020 Jan 7. doi: 10.1002/anie.201916362.

Abstract

The synthesis and reactivity study of the first isolable boraphosphaketene, cyclic(alkyl)(amino) carbene (CAAC)-borafluorene-P=C=O (2), is described. Photolysis of compound 2 results in the formation of CAAC-stabilized BP-doped phenanthryne (3) through tandem decarbonylation, monoatomic phosphide insertion, and ring-expansion. Notably, while BN-doped phenanthryne was previously discussed as a reactive intermediate which could not be isolated, the heavier BP-doped analogue exhibits remarkable solution and solid-state stability. The reactivity of 2 with stable carbenes was also explored. Addition of CAAC to 2 led to migration of the original CAAC ligand from boron to phosphorus and coordination of the added CAAC to carbon, affording compound 4. Reaction of 1,3-diisopropyl-4,5-dimethylimidazol-2-ylidene (NHC) with 2 resulted in N-C bond activation to give the unusual spiro-heterocyclic compound (5).

Last updated on 01/17/2021