Unparalleled rates for the activation of aryl chlorides and bromides: Coupling with amines and boronic acids in minutes at room temperature

被引:344
作者
Stambuli, JP [1 ]
Kuwano, R [1 ]
Hartwig, JF [1 ]
机构
[1] Yale Univ, Dept Chem, New Haven, CT 06520 USA
关键词
D O I
10.1002/anie.200290036
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Exceptionally fast oxidative addition of an aryl chloride (or a deactivated aryl bromide) to the active Pd0 center, which is ligated by sterically demanding phosphanes, occurs during coupling reactions catalyzed by air-stable Pd1 dimers as shown in the scheme. As a result, the reactions of aryl chlorides and bromides with amines and boronic acids at room temperature are complete within a few minutes. 1-Ad = 1-adamantyl.
引用
收藏
页码:4746 / 4748
页数:3
相关论文
共 24 条
[1]   Mechanistic studies of the palladium-catalyzed amination of aryl halides and the oxidative addition of aryl bromides to Pd(BINAP)2 and Pd(DPPF)2:: An unusual case of zero-order kinetic behavior and product inhibition [J].
Alcazar-Roman, LM ;
Hartwig, JF ;
Rheingold, AL ;
Liable-Sands, LM ;
Guzei, IA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (19) :4618-4630
[2]   Mechanism of aryl chloride amination: Base-induced oxidative addition [J].
Alcazar-Roman, LM ;
Hartwig, JF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (51) :12905-12906
[3]   Anionic Pd(0) and Pd(II) intermediates in palladium-catalyzed Heck and cross-coupling reactions [J].
Amatore, C ;
Jutand, A .
ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (05) :314-321
[4]  
[Anonymous], ANGEW CHEM
[5]  
Crabtree R.H., 2001, The Organometallic Chemistry of the Transition Metals, V3rd
[6]  
Drew D., 1972, INORG SYNTH, V13, P47, DOI DOI 10.1002/9780470132449.CH11
[7]   Reactivity studies of [Pd2(μ-X)2(PBu3t)2] (X = Br, I) with CNR (R=2,6-dimethylphenyl), H2 and alkynes [J].
Durà-Vilà, V ;
Mingos, DMP ;
Vilar, R ;
White, AJP ;
Williams, DJ .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2000, 600 (1-2) :198-205
[8]   Amination reactions of aryl halides with nitrogen-containing reagents mediated by palladium/imidazolium salt systems [J].
Grasa, GA ;
Viciu, MS ;
Huang, JK ;
Nolan, SP .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (23) :7729-7737
[9]  
Gstcttmayr C. W. K., 2002, ANGEW CHEM, V114, P1421
[10]  
Gstöttmayr CWK, 2002, ANGEW CHEM INT EDIT, V41, P1363, DOI 10.1002/1521-3773(20020415)41:8<1363::AID-ANIE1363>3.0.CO