Complexes of Borane and N-Heterocyclic Carbenes: A New Class of Radical Hydrogen Atom Donor
Journal of the American Chemical Society2008Vol. 130(31), pp. 10082–10083
Citations Over TimeTop 10% of 2008 papers
Shau‐Hua Ueng, Malika Makhlouf Brahmi, Étienne Derat, Louis Fensterbank, Emmanuel Lacôte, Max Malacrìa, Dennis P. Curran
Abstract
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.
Related Papers
- → Twenty-five years of bis-pentafluorophenyl borane: a versatile reagent for catalyst and materials synthesis(2019)88 cited
- → Highly efficient synthesis of chiral β-hydroxy sulfides with high enantiomeric purity via CBS-oxazaborolidine-catalyzed borane reduction(2002)56 cited
- → Reaction of 1,3,5-diazaphosphorinanes with borane(1989)1 cited
- → Synthesis of Functional Methylphosphane-Borane Derivatives. II. Syntheses of Chlorodimethylphosphane-Borane, Dimethyl(amino)phosphane-borane and Sodium (Boranato-Dimethylphosphinite): Precursors for the Chemistry of the H3B(CH3)2P-Group(1985)4 cited
- → ChemInform Abstract: SYNTHESIS OF 3 TYPES OF BORON DERIVATIVE: TRIS(N‐BORANE)AMINOBORIC ESTERS, BIS(N‐BORANE)AMINOBORIC ESTERS, AND N‐BORANEAMINO FROM THE REACTION OF α‐AMINO ALCOHOLS WITH BORANE/THF AND BORANE/DIMETHYL SULFIDE. EVIDENCE FOR AN INTERNAL N → B COORDINATION(1982)