2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)/tert-Butyl Nitrite/Oxygen: A Versatile Catalytic Oxidation System

被引:104
作者
Shen, Zhenlu [1 ]
Dai, Jialiang [1 ]
Xiong, Jie [1 ]
He, Xijun [1 ]
Mo, Weimin [1 ]
Hu, Baoxiang [1 ]
Sun, Nan [1 ]
Hu, Xinquan [1 ,2 ]
机构
[1] Zhejiang Univ Technol, Coll Chem Engn & Mat Sci, Hangzhou 310014, Zhejiang, Peoples R China
[2] Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China
基金
中国国家自然科学基金;
关键词
alcohols; deprotection; 2; 3-dichloro-5; 6-dicyano-1; 4-benzoquinone (DDQ); oxidation; oxygen; TRANSITION-METAL-FREE; C BOND FORMATION; AEROBIC OXIDATION; HIGHLY EFFICIENT; PROTECTING GROUP; BENZYL ETHERS; SELECTIVE OXIDATION; MOLECULAR-OXYGEN; DDQ; ALCOHOLS;
D O I
10.1002/adsc.201100429
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A new catalytic oxidation system using catalytic amounts of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) and tert-butyl nitrite with molecular oxygen serving as the environmentally benign, terminal oxidant has been developed. This aerobic catalytic system was established for the selective oxidation of non-sterically hindered benzylic alcohols and electron-rich benzyl methyl ethers, and successfully extended to an application in the oxidative deprotection of PMB ethers to the alcohols in high selectivity.
引用
收藏
页码:3031 / 3038
页数:8
相关论文
共 77 条
[1]   Iridium- and rhodium-catalyzed [2+2+2] cycloadditions of diynes with maleimide:: A new synthetic route to highly substituted phthalimides [J].
Alvarez, Leonardo X. ;
Bessieres, Bernard ;
Einhorn, Jacques .
SYNLETT, 2008, (09) :1376-1380
[2]   Combined redox couples for catalytic oxidation of methane by dioxygen at low temperatures [J].
an, Zengji An ;
Pan, Xiulian ;
Liu, Xiumei ;
Han, Xiuwen ;
Bao, Xinhe .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (50) :16028-16029
[3]  
[Anonymous], 2006, ANGEW CHEM
[4]  
[Anonymous], 2004, MODERN OXIDATION MET
[5]   Oxidative nucleophilic Substitution(SNOX) of the benzylic position as a tunable synthesis of tetrahydroisoquinoline natural alkaloid analogues [J].
Aubry, Sylvain ;
Pellet-Rostaing, Stephane ;
Lemaire, Marc .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (31) :5212-5225
[6]   QUINONE DEHYDROGENATION - OXIDATION OF BENZYLIC ALCOHOLS WITH 2,3-DICHLORO-5,6-DICYANOBENZOQUINONE [J].
BECKER, HD ;
BJORK, A ;
ADLER, E .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (09) :1596-1600
[7]   Efficient synthesis of functionalized furans and benzofurans based on a '[3+2] cyclization/oxidation' strategy [J].
Bellur, E ;
Freifeld, I ;
Langer, P .
TETRAHEDRON LETTERS, 2005, 46 (13) :2185-2187
[8]   2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) [J].
Bharate, SB .
SYNLETT, 2006, (03) :496-497
[9]   PREPARATION OF ALKYLARYLCARBINOLS BY MONO-OXIDATION AT THE BENZYLIC POSITION USING 2,3-DICHLORO-5,6-DICYANOBENZOQUINONE (DDQ) [J].
BOUQUET, M ;
GUY, A ;
LEMAIRE, M ;
GUETTE, JP .
SYNTHETIC COMMUNICATIONS, 1985, 15 (13) :1153-1157
[10]   Large-scale oxidations in the pharmaceutical industry [J].
Caron, Stephane ;
Dugger, Robert W. ;
Ruggeri, Sally Gut ;
Ragan, John A. ;
Ripin, David H. Brown .
CHEMICAL REVIEWS, 2006, 106 (07) :2943-2989