Polarity reversal catalysis in radical reductions of halides by N-heterocyclic carbene boranes
…, E Lacôte, J Lalevée, DP Curran
Index: Pan, Xiangcheng; Lacote, Emmanuel; Lalevee, Jacques; Curran, Dennis P. Journal of the American Chemical Society, 2012 , vol. 134, # 12 p. 5669 - 5674
Full Text: HTML
Citation Number: 65
Abstract
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 [C9H19C (CH3) 2SH]. Rate constants for reaction of the phenylthiyl (PhS•) radical with two NHC- ...
Related Articles:
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. Journal of the American Chemical Society, 2008 , vol. 130, # 31 p. 10082 - 10083]
[Nakano, Masakazu; Matsuo, Jun-Ichi; Mukaiyama, Teruaki Chemistry Letters, 2000 , # 12 p. 1352 - 1353]
A discriminating protecting group strategy for alcohols and amines
[Liotta, Louis J.; Ganem, Bruce Israel Journal of Chemistry, 1991 , vol. 31, # 3 p. 215 - 222]
Benzylation of alcohols by using bis [acetylacetonato] copper as catalyst
[Sirkecioglu, Okan; Karliga, Bekir; Talinli, Naciye Tetrahedron Letters, 2003 , vol. 44, # 46 p. 8483 - 8485]
[Bhatt; Shin, Dong-Soo; Falck; Mioskowski, Charles Tetrahedron Letters, 1992 , vol. 33, # 34 p. 4885 - 4888]