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Disulfides and Boryl Sulfides Serve as both Initiators and Precatalysts in Radical Reductions of Halides by an N‐Heterocyclic Carbene⋅Borane
Author(s) -
Pan Xiangcheng,
Lalevée Jacques,
Lacôte Emmanuel,
Curran Dennis P.
Publication year - 2013
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201300752
Subject(s) - chemistry , carbene , borane , thiophenol , catalysis , halide , medicinal chemistry , alkyl , aryl , sulfide , polymer chemistry , organic chemistry , photochemistry
Diphenyl disulfide (PhSSPh), a typical boryl monosulfide (di i Pr‐Imd‐BH 2 SPh) and a typical boryl bis‐sulfide [diMe‐Imd‐BH(SPh) 2 ] all serve as both initiators and precatalysts in the reduction of alkyl and aryl halides by readily available 1,3‐dimethylimidazol‐2‐ylidene⋅borane (diMe‐Imd‐BH 3 ). The reactions are suggested to occur by a polarity reverse catalysis mechanism where in situ generated thiophenol is the active catalyst.