A chemoselective aerobic oxidation of benzylic azides catalyzed by molybdenum xanthate in an aqueous medium

被引:36
作者
Maddani, Mahagundappa [1 ]
Prabhu, Kandikere Ramaiah [1 ]
机构
[1] Indian Inst Sci, Dept Organ Chem, Bangalore 560012, Karnataka, India
关键词
benzyl azides; molybdenum; redox reactions; aerobic oxidations; chemoselectivity; green chemistry;
D O I
10.1016/j.tetlet.2008.05.047
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A mild molybdenum-catalyzed, aerobic, chemoselective oxidation of benzylic azides to the corresponding aldehydes in an aqueous medium that tolerates a variety of functional groups including alcohols, esters, ketones, halides and olefins is described. (c) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4526 / 4530
页数:5
相关论文
共 43 条
[1]   DIOXOMOLYBDENUM(VI) HALIDES AS OXOTRANSFER CATALYSTS [J].
ARNAIZ, FJ ;
AGUADO, R ;
DEILARDUYA, JMM .
POLYHEDRON, 1994, 13 (23) :3257-3259
[2]   Molybdenum-oxo chemistry in various aspects of oxygen atom transfer processes [J].
Arzoumanian, H .
COORDINATION CHEMISTRY REVIEWS, 1998, 178 :191-202
[3]   Enantioselective oxidation of olefins catalyzed by a chiral bishydroxamic acid complex of molybdenum [J].
Barlan, Allan U. ;
Basak, Arindrajit ;
Yamamoto, Hisashi .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (35) :5849-5852
[4]  
BARRAL R, 1972, TETRAHEDRON LETT, V13, P1963
[5]   METAL CATALYSIS IN OXIDATION BY PEROXIDES .28. ANIONIC MOLYBDENUM-PICOLINATE N-OXIDO-PEROXO COMPLEX - AN EFFECTIVE OXIDANT OF PRIMARY AND SECONDARY ALCOHOLS IN NONPOLAR-SOLVENTS [J].
BORTOLINI, O ;
CAMPESTRINI, S ;
DIFURIA, F ;
MODENA, G ;
VALLE, G .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (24) :5467-5469
[6]   Oxidation of thiols with molecular oxygen catalyzed by cobalt(II) phthalocyanines in ionic liquid [J].
Chauhan, SMS ;
Kumar, A ;
Srinivas, KA .
CHEMICAL COMMUNICATIONS, 2003, (18) :2348-2349
[7]   SYNTHESIS OF MO(IV) AND MO(V) COMPLEXES USING OXO ABSTRACTION BY PHOSPHINES - MECHANISTIC IMPLICATIONS [J].
CHEN, GJJ ;
MCDONALD, JW ;
NEWTON, WE .
INORGANIC CHEMISTRY, 1976, 15 (11) :2612-2615
[8]   A recyclable catalyst that precipitates at the end of the reaction [J].
Dioumaev, VK ;
Bullock, RM .
NATURE, 2003, 424 (6948) :530-532
[9]   Development and semicommercial implementation of an environmentally benign, hydrogen peroxide mediated oxidation of aliphatic alcohols [J].
Dudas, J ;
Parkinson, CJ ;
Cukan, V ;
Chokwe, TB .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2005, 9 (06) :976-981
[10]   Synthetic analogues and reaction systems relevant to the molybdenum and tungsten oxotransferases [J].
Enemark, JH ;
Cooney, JJA .
CHEMICAL REVIEWS, 2004, 104 (02) :1175-1200