Efficient and selective Al-catalyzed alcohol oxidation via Oppenauer chemistry

被引:73
作者
Graves, Christopher R.
Zeng, Bi-Shun
Nguyen, SonBinh T.
机构
[1] Northwestern Univ, Dept Chem, Evanston, IL 60208 USA
[2] Northwestern Univ, Inst Environm Catalysis, Evanston, IL 60208 USA
关键词
D O I
10.1021/ja063842s
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A highly active and selective Al-based catalytic Oppenauer (O) oxidation is reported. Quantitative and selective oxidations of a variety of benzylic, propargylic, allylic, and aliphatic primary and secondary alcohols were achieved using nitrobenzaldehyde derivatives as the oxidant and simple aluminum compounds as precatalysts. Copyright © 2006 American Chemical Society.
引用
收藏
页码:12596 / 12597
页数:2
相关论文
共 23 条
[1]   Relative oxidation-reduction reactivities of ketones and aldehydes and applications in synthesis [J].
Adkins, H ;
Cox, FW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1938, 60 :1151-1159
[2]   THE OXIDATION POTENTIALS OF ALDEHYDES AND KETONES [J].
ADKINS, H ;
ELOFSON, RM ;
ROSSOW, AG ;
ROBINSON, CC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1949, 71 (11) :3622-3629
[3]   Transition metal hydrides as active intermediates in hydrogen transfer reactions [J].
Bäckvall, JE .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2002, 652 (1-2) :105-111
[4]   Catalytic Meerwein-Pondorf-Verley reduction by simple aluminum complexes [J].
Campbell, EJ ;
Zhou, HY ;
Nguyen, ST .
ORGANIC LETTERS, 2001, 3 (15) :2391-2393
[5]   The mechanism of aluminum-catalyzed Meerwein-Schmidt-Ponndorf-Verley reduction of carbonyls to alcohols [J].
Cohen, R ;
Graves, CR ;
Nguyen, SBT ;
Martin, JML ;
Ratner, MA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (45) :14796-14803
[6]  
COREY EJ, 1975, TETRAHEDRON LETT, P2647
[7]  
COREY EJ, 1979, TETRAHEDRON LETT, P399
[8]   MEERWEIN-PONNDORF-VERLEY REDUCTIONS AND OPPENAUER OXIDATIONS - AN INTEGRATED APPROACH [J].
DEGRAAUW, CF ;
PETERS, JA ;
VANBEKKUM, H ;
HUSKENS, J .
SYNTHESIS-STUTTGART, 1994, (10) :1007-1017
[9]   A USEFUL 12-I-5 TRIACETOXYPERIODINANE (THE DESS-MARTIN PERIODINANE) FOR THE SELECTIVE OXIDATION OF PRIMARY OR SECONDARY ALCOHOLS AND A VARIETY OF RELATED 12-I-5 SPECIES [J].
DESS, DB ;
MARTIN, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (19) :7277-7287
[10]  
DJERASSI C, 1951, ORG REACTIONS, V6, P207