Nicotinoyl azide (NCA)-mediated Mitsunobu reaction: an expedient one-pot transformation of alcohols into azides
G Papeo, H Posteri, P Vianello, M Varasi
Index: Papeo, Gianluca; Posteri, Helena; Vianello, Paola; Varasi, Mario Synthesis, 2004 , # 17 p. 2886 - 2892
Full Text: HTML
Citation Number: 21
Abstract
Our interest in using a cheap and easily accessible source of azide ion in Mitsunobu-type reactions, prompted us to test aroyl azides as reagents. We hoped that the Morrison-Brunn-Huisgen (MBH) betaine [19] (1, Scheme [1] ) would trigger the release of the nucleophile via formation of the oxyphosphonium ion intermediate (2, Scheme [1] ) which would undergo the classical S N 2 reaction with azide ion. Generation of the oxyphosphonium ions should, in ...
Related Articles:
[Sangshetti, Jaiprakash N.; Nagawade, Rahul R.; Shinde, Devanand B. Bioorganic and Medicinal Chemistry Letters, 2009 , vol. 19, # 13 p. 3564 - 3567]
[Moore, Kevin W.; Bonner, Katrine; Jones, Elizabeth A.; Emms, Frances; Leeson, Paul D.; Marwood, Rosemary; Patel, Shil; Patel, Smita; Rowley, Michael; Thomas, Steven; Carling, Robert W. Bioorganic and Medicinal Chemistry Letters, 1999 , vol. 9, # 9 p. 1285 - 1290]
[Bioorganic and Medicinal Chemistry Letters, , vol. 11, # 18 p. 2475 - 2479]
[Bioorganic and Medicinal Chemistry Letters, , vol. 11, # 18 p. 2475 - 2479]