1043905-82-3Relevant articles and documents
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.
Complexes of borane and N-heterocyclic carbenes: A new class of radical hydrogen atom donor
Ueng, Shau-Hua,Brahmi, Malika Makhlouf,Derat, Etienne,Fensterbank, Louis,Lacote, Emmanuel,Malacria, Max,Curran, Dennis P.
supporting information; experimental part, p. 10082 - 10083 (2009/02/04)
Calculations suggest that complexes of borane with N-heterocyclic carbenes (NHC) have B-H bond dissocation energies more then 20 kcal/mol less than free borane, diborane, borane-THF, and related complexes. Values are in the range of popular radical hydrogen atom donors like tin hydrides (70-80 kcal/mol). The resulting prediction that NHC borane complexes could be used as radical hydrogen atom donors was verified by radical deoxygenations of xanthates by using either AIBN or triethylborane as initiator. Copyright
