Spiroborate catalyzed reductions with N, N-diethylaniline borane
BM Coleridge, TP Angert, LR Marks, PN Hamilton…
Index: Coleridge, Brian M.; Angert, Thomas P.; Marks, Lucas R.; Hamilton, Patrick N.; Sutton, Christopher P.; Matos, Karl; Burkhardt, Elizabeth R. Tetrahedron Letters, 2010 , vol. 51, # 46 p. 5973 - 5976
Full Text: HTML
Citation Number: 5
Abstract
Reduction of esters, amides, and ketones by N, N-diethylaniline borane is accelerated by catalysts derived from spiroborate complexes. Esters are reduced at ambient temperature in less than 4h with this amine borane and 5mol% spiroborate 6. Functional group selectivity shows ketone and tertiary amide reduction is faster than ester or nitrile reduction.
Related Articles:
Aminomethylation of organic halides promoted by zinc in protic medium
[Estevam, Idalia H. S.; Da Silva, Margarete F.; Bieber, Lothar W. Tetrahedron Letters, 2005 , vol. 46, # 44 p. 7601 - 7604]
Iridium-catalyzed reduction of secondary amides to secondary amines and imines by diethylsilane
[Park, Sehoon; Brookhart, Maurice Journal of the American Chemical Society, 2012 , vol. 134, # 1 p. 640 - 653]
The behavior of aliphatic aldehydes in the Leuckart-Wallach reaction
[de Benneville; Macartney Journal of the American Chemical Society, 1950 , vol. 72, p. 3073]
[Wu, Shune-Long; Tao, Yu-Tai; Saunders, William H. Journal of the American Chemical Society, 1984 , vol. 106, p. 7583 - 7588]
Ruthenium-catalyzed ionic hydrogenation of aziridinium cations
[Taniguchi, Yuki; Horie, Shiro; Takaki, Ken; Fujiwara, Yuzo Journal of Organometallic Chemistry, 1995 , vol. 504, # 1-2 p. 137 - 142]