Aerobic oxidation catalysis with stable radicals

被引:316
作者
Cao, Qun [1 ]
Dornan, Laura M. [1 ]
Rogan, Luke [1 ]
Hughes, N. Louise [1 ]
Muldoon, Mark J. [1 ]
机构
[1] Queens Univ Belfast, Sch Chem & Chem Engn, Belfast BT9 5AG, Antrim, North Ireland
关键词
TRANSITION-METAL-FREE; HIGHLY-ACTIVE ORGANOCATALYST; C-H OXIDATION; ALCOHOL OXIDATION; SELECTIVE OXIDATION; MOLECULAR-OXYGEN; N-OXYL; BENZYLIC ALCOHOLS; PRIMARY AMINES; SUPPORTED TEMPO;
D O I
10.1039/c3cc47081d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Selective oxidation reactions are challenging when carried out on an industrial scale. Many traditional methods are undesirable from an environmental or safety point of view. There is a need to develop sustainable catalytic approaches that use molecular oxygen as the terminal oxidant. This review will discuss the use of stable radicals (primarily nitroxyl radicals) in aerobic oxidation catalysis. We will discuss the important advances that have occurred in recent years, highlighting the catalytic performance, mechanistic insights and the expanding synthetic utility of these catalytic systems.
引用
收藏
页码:4524 / 4543
页数:20
相关论文
共 206 条
[1]   Intensification of TEMPO-mediated aerobic alcohol oxidations under three-phase flow conditions [J].
Aellig, Christof ;
Scholz, David ;
Conrad, Sabrina ;
Hermans, Ive .
GREEN CHEMISTRY, 2013, 15 (07) :1975-1980
[2]   Enantioselective Oxidative Coupling of 2-Naphthol Derivatives by Copper-(R)-1,1′-Binaphthyl-2,2′-diamine-TEMPO Catalyst [J].
Alamsetti, Santosh Kumar ;
Poonguzhali, Elamvazhuthi ;
Ganapathy, Dhandapani ;
Sekar, Govindasamy .
ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (14-15) :2803-2808
[3]   Aerobic Copper-Catalyzed Organic Reactions [J].
Allen, Scott E. ;
Walvoord, Ryan R. ;
Padilla-Salinas, Rosaura ;
Kozlowski, Marisa C. .
CHEMICAL REVIEWS, 2013, 113 (08) :6234-6458
[4]  
ANELLI PL, 1987, J ORG CHEM, V52, P2559
[5]   TEMPO-catalyzed aerobic oxidation of alcohols to aldehydes and ketones in ionic liquid [bmim][PF6] [J].
Ansari, IA ;
Gree, R .
ORGANIC LETTERS, 2002, 4 (09) :1507-1509
[6]   New mediators for the enzyme laccase: mechanistic features and selectivity in the oxidation of non-phenolic substrates [J].
Astolfi, P ;
Brandi, P ;
Galli, C ;
Gentili, P ;
Gerini, MF ;
Greci, L ;
Lanzalunga, O .
NEW JOURNAL OF CHEMISTRY, 2005, 29 (10) :1308-1317
[7]  
Backvall J. E., 2010, MODERN OXIDATION MET
[8]   KINETICS OF NITROXIDE RADICAL TRAPPING .1. SOLVENT EFFECTS [J].
BECKWITH, ALJ ;
BOWRY, VW ;
INGOLD, KU .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (13) :4983-4992
[9]   Cu(bipy)2+/TEMPO-Catalyzed Oxidation of Alcohols: Radical or Nonradical Mechanism? [J].
Belanzoni, Paola ;
Michel, Carine ;
Baerends, Evert Jan .
INORGANIC CHEMISTRY, 2011, 50 (23) :11896-11904
[10]   Selective aerobic oxidation of alcohols with a combination of a polyoxometalate and nitroxyl radical as catalysts [J].
Ben-Daniel, R ;
Alsters, P ;
Neumann, R .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (25) :8650-8653