Room-Temperature Alternative to the Arbuzov Reaction: The Reductive Deoxygenation of Acyl Phosphonates
SMA Kedrowski, DA Dougherty
Index: Kedrowski, Sean M. A.; Dougherty, Dennis A. Organic Letters, 2010 , vol. 12, # 18 p. 3990 - 3993
Full Text: HTML
Citation Number: 16
Abstract
The reductive deoxygenation of acyl phosphonates using a Wolff− Kishner-like sequence is described. This transformation allows direct access to alkyl phosphonates from acyl phosphonates at room temperature. The method can be combined with acyl phosphonate synthesis into a one pot, four-step procedure for the conversion of carboxylic acids into alkyl phosphonates. The methodology works well for a variety of aliphatic acids and shows a ...
Related Articles:
Synthesis of dialkyl and diaryl benzylphosphonates through a ZnI 2-mediated reaction
[Richardson, Rebekah M.; Barney, Rocky J.; Wiemer, David F. Tetrahedron Letters, 2012 , vol. 53, # 49 p. 6682 - 6684]
Copper??Catalyzed Synthesis of Alkylphosphonates from H??Phosphonates and N??Tosylhydrazones
[Miao, Wenjun; Gao, Yuzhen; Li, Xueqin; Gao, Yuxing; Tang, Guo; Zhao, Yufen Advanced Synthesis and Catalysis, 2012 , vol. 354, # 14-15 p. 2659 - 2664]
Photo-Arbuzov rearrangements of benzyl phosphites
[Omelanzcuk, Jan; Sopchik, Alan E.; Lee, Sueg-Geun; Akutagawa, Kunihiko; Cairns, Matthew S.; Bentrude, Wesley G. Journal of the American Chemical Society, 1988 , vol. 110, # 20 p. 6908 - 6909]
[Laven, Gaston; Stawinski, Jacek Synlett, 2009 , # 2 p. 225 - 228]
[Laven, Gaston; Stawinski, Jacek Synlett, 2009 , # 2 p. 225 - 228]