A versatile catalyst for Heck reactions of aryl chlorides and aryl bromides under mild conditions

被引:670
作者
Littke, AF [1 ]
Fu, GC [1 ]
机构
[1] MIT, Dept Chem, Cambridge, MA 02139 USA
关键词
D O I
10.1021/ja010988c
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
In the presence of Cy2NMe, PdlP(t-Bu)(3) serves as an exceptionally mild and versatile catalyst for Heck reactions of aryl chlorides and bromides. A sterically and electronically diverse array of aryl bromides, as well as activated aryl chlorides, couple with a range of mono- and disubstituted olefins at room temperature, furnishing the arylated product with high E/Z stereoselection. The corresponding reactions of a broad spectrum of electron-neutral and electron-rich aryl chlorides proceed at elevated temperature, also with high selectivity. In terms of scope and mildness, Pd/P(t-Bu)(3)/Cy2NMe represents an advance over previously reported catalysts for these Heck coupling processes.
引用
收藏
页码:6989 / 7000
页数:12
相关论文
共 121 条
[21]   Access to well-defined heterogeneous catalytic systems via ring-opening metathesis polymerization (ROMP): Applications in palladium(II)-mediated coupling reactions [J].
Buchmeiser, MR ;
Wurst, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (48) :11101-11107
[22]   Use of a heck reaction for the synthesis of a new α-azido phosphotyrosyl mimetic suitably protected for peptide synthesis [J].
Burke, TR ;
Liu, DG ;
Gao, Y .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (19) :6288-6291
[23]   ALPHA-REGIOSELECTIVITY IN PALLADIUM-CATALYZED ARYLATION OF ACYCLIC ENOL ETHERS [J].
CABRI, W ;
CANDIANI, I ;
BEDESCHI, A ;
PENCO, S ;
SANTI, R .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (05) :1481-1486
[24]   RECENT DEVELOPMENTS AND NEW PERSPECTIVES IN THE HECK REACTION [J].
CABRI, W ;
CANDIANI, I .
ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (01) :2-7
[25]   1,10-PHENANTHROLINE DERIVATIVES - A NEW LIGAND CLASS IN THE HECK REACTION - MECHANISTIC ASPECTS [J].
CABRI, W ;
CANDIANI, I ;
BEDESCHI, A ;
SANTI, R .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (26) :7421-7426
[26]   Heck reaction in ionic liquids catalyzed by a Pd-benzothiazole carbene complex [J].
Calò, V ;
Nacci, A ;
Lopez, L ;
Mannarini, N .
TETRAHEDRON LETTERS, 2000, 41 (46) :8973-8976
[27]   PALLADIUM-CATALYZED VINYL SUBSTITUTION-REACTIONS .2. SYNTHESIS OF ARYL SUBSTITUTED ALLYLIC ALCOHOLS, ALDEHYDES, AND KETONES FROM ARYL HALIDES AND UNSATURATED ALCOHOLS [J].
CHALK, AJ ;
MAGENNIS, SA .
JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (07) :1206-1209
[28]  
Crisp GT, 1998, CHEM SOC REV, V27, P427
[29]   The first general method for palladium-catalyzed Negishi cross-coupling of aryl and vinyl chlorides:: Use of commercially available Pd(P(t-BU)3)2 as a catalyst [J].
Dai, CY ;
Fu, GC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (12) :2719-2724
[30]   Total synthesis of baccatin III and taxol [J].
Danishefsky, SJ ;
Masters, JJ ;
Young, WB ;
Link, JT ;
Snyder, LB ;
Magee, TV ;
Jung, DK ;
Isaacs, RCA ;
Bornmann, WG ;
Alaimo, CA ;
Coburn, CA ;
DiGrandi, MJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (12) :2843-2859