1367875-29-3Relevant academic research and scientific papers
Polarity reversal catalysis in radical reductions of halides by N-heterocyclic carbene boranes
Pan, Xiangcheng,Lacote, Emmanuel,Lalevee, Jacques,Curran, Dennis P.
, p. 5669 - 5674 (2012/06/04)
Otherwise sluggish or completely ineffective radical reductions of alkyl and aryl halides by N-heterocyclic carbene boranes (NHC-boranes) are catalyzed by thiols. Reductions and reductive cyclizations with readily available 1,3-dimethylimidazol-2-ylidene borane and a water-soluble triazole relative are catalyzed by thiophenol and tert-dodecanethiol [C9H 19C(CH3)2SH]. Rate constants for reaction of the phenylthiyl (PhS?) radical with two NHC-boranes have been measured to be ～108 M-1 s-1 by laser flash photolysis experiments. An analysis of the available evidence suggests the operation of polarity reversal catalysis.
