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

被引:663
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
    Buchmeiser, MR
    Wurst, K
    [J]. 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
    Burke, TR
    Liu, DG
    Gao, Y
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (19) : 6288 - 6291
  • [23] ALPHA-REGIOSELECTIVITY IN PALLADIUM-CATALYZED ARYLATION OF ACYCLIC ENOL ETHERS
    CABRI, W
    CANDIANI, I
    BEDESCHI, A
    PENCO, S
    SANTI, R
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (05) : 1481 - 1486
  • [24] RECENT DEVELOPMENTS AND NEW PERSPECTIVES IN THE HECK REACTION
    CABRI, W
    CANDIANI, I
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (01) : 2 - 7
  • [25] 1,10-PHENANTHROLINE DERIVATIVES - A NEW LIGAND CLASS IN THE HECK REACTION - MECHANISTIC ASPECTS
    CABRI, W
    CANDIANI, I
    BEDESCHI, A
    SANTI, R
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (26) : 7421 - 7426
  • [26] Heck reaction in ionic liquids catalyzed by a Pd-benzothiazole carbene complex
    Calò, V
    Nacci, A
    Lopez, L
    Mannarini, N
    [J]. 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
    CHALK, AJ
    MAGENNIS, SA
    [J]. 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
    Dai, CY
    Fu, GC
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (12) : 2719 - 2724
  • [30] Total synthesis of baccatin III and taxol
    Danishefsky, SJ
    Masters, JJ
    Young, WB
    Link, JT
    Snyder, LB
    Magee, TV
    Jung, DK
    Isaacs, RCA
    Bornmann, WG
    Alaimo, CA
    Coburn, CA
    DiGrandi, MJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (12) : 2843 - 2859