Insertion of reactive rhodium carbenes into boron-hydrogen bonds of stable N-heterocyclic carbene boranes.

TitleInsertion of reactive rhodium carbenes into boron-hydrogen bonds of stable N-heterocyclic carbene boranes.
Publication TypeJournal Article
Year of Publication2013
AuthorsLi X, Curran DP
JournalJournal of the American Chemical Society
Volume135
Issue32
Pagination12076-81
Date Published2013 Aug 14
Abstract

Readily available rhodium(II) salts catalyze reactions between NHC-boranes (NHC-BH3) and diazocarbonyl compounds (N2CRCOR'). Stable α-NHC-boryl carbonyl compounds (NHC-BH2-CHRCOR') are isolated in good yields. The reaction is a reliable way to make boron-carbon bonds with good tolerance for variation in both the NHC-borane and diazocarbonyl components. It presumably occurs by insertion of a transient rhodium carbene into a boron-hydrogen bond of the NHC-borane. Competitive experiments show that a typical NHC-borane is highly reactive toward rhodium carbenes.

DOI10.1371/journal.pone.0069942
Alternate JournalJ. Am. Chem. Soc.