C?X (X=Br, I) Bond-Tolerant Aerobic Oxidative Cross- Coupling: A Strategy to Selectively Construct ß-Aryl Ketones and Aldehydes

被引:47
作者
Chen, Mao [1 ]
Wang, Jie [1 ]
Chai, Ziyi [1 ]
You, Cai [1 ]
Lei, Aiwen [1 ,2 ]
机构
[1] Wuhan Univ, Coll Chem & Mol Sci, Wuhan 430072, Hubei, 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
copper; cross-coupling; oxygen; palladium; selectivity; CATALYZED ASYMMETRIC 1,4-ADDITION; SUBSTITUTED ALLYLIC ALCOHOLS; MOLECULAR-OXYGEN; CONJUGATE ADDITION; ARYLBORONIC ACIDS; HECK REACTION; UNSATURATED ALCOHOLS; OXIDASE CATALYSIS; ELECTRON-TRANSFER; ORGANIC HALIDES;
D O I
10.1002/adsc.201100782
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Using moelcular oxygen as the terminal oxidant, various aryl halide-containing beta-aryl ketones and aldehydes can be synthesized directly from readily available allyic alcohols and boronic acids via palladium-catalyzed oxidative cross-coupling reactions. The dual roles of copper, including electron-carrier and Lewis acid functions, are supposed to be critical for the high reactivity and selectivity of this aerobic oxidative coupling transformation.
引用
收藏
页码:341 / 346
页数:6
相关论文
共 75 条
[1]   Dioxygen-promoted regioselective oxidative Heck arylations of electron-rich olefins with arylboronic acids [J].
Andappan, MMS ;
Nilsson, P ;
von Schenck, H ;
Larhed, M .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (16) :5212-5218
[2]  
[Anonymous], 2008, ANGEW CHEM
[3]  
[Anonymous], 2008, ANGEW CHEM
[4]  
[Anonymous], 2010, ANGEW CHEM
[5]  
[Anonymous], 2008, ANGEW CHEM, DOI DOI 10.1002/ANGE.200704495
[6]  
[Anonymous], 1999, HDB NATURAL FLAVONOI
[7]   The heck reaction as a sharpening stone of palladium catalysis [J].
Beletskaya, IP ;
Cheprakov, AV .
CHEMICAL REVIEWS, 2000, 100 (08) :3009-3066
[8]   NITROGEN ACIDS .1. CARBOXAMIDES AND SULFONAMIDES [J].
BORDWELL, FG ;
ALGRIM, D .
JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (14) :2507-2508
[9]   Concise synthesis of dihydrochalcones via palladium-catalyzed coupling of aryl halides and 1-aryl-2-propen-1-ols [J].
Briot, A ;
Baehr, C ;
Brouillard, R ;
Wagner, A ;
Mioskowski, C .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (04) :1374-1377
[10]  
Cahiez G., 2009, ANGEW CHEM, V121, P6859