Palladium-catalyzed Heck alkynylation of benzyl chlorides

被引：41
|
作者：
Larsen, Catharine H. [1 ]
Anderson, Kevin W. [1 ]
Tundel, Rachel E. [1 ]
Buchwald, Stephen L. [1 ]
机构：
[1] MIT, Dept Chem, Cambridge, MA 02139 USA
来源：
SYNLETT | 2006年 / 18期
关键词：
palladium; alkynes; Heck alkynylation; benzyl chlorides; allene;
D O I：
10.1055/s-2006-949625
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient and general protocol for the palladium-catalyzed Heck alkynylation of benzyl chlorides was developed. A catalyst system comprised of PdCl2(CH3CN)(2) and 2-dicyclohexyl-phosphino-2',4',6'-triisopropylbiphenyI (XPhos), with CS2CO3 as the base, efficiently couples a wide range of functionalized terminal alkynes and substituted benzyl chlorides at 65 degrees C. We have also demonstrated that the corresponding aryl allene product can be selected for using an excess amount of base and higher reaction temperatures (80 degrees C) in a one-pot procedure.
引用
收藏
页码：2941 / 2946
页数：6
相关论文
共 50 条
  • [21] Palladium-catalyzed amination of aryl chlorides
    Reddy, N. P.
    Tanaka, M.
    Tetrahedron Letters, 38 (27):
  • [22] Palladium-Catalyzed Desulfitative Cross-Coupling Reaction of Sodium Sulfinates with Benzyl Chlorides
    Zhao, Feng
    Tan, Qi
    Xiao, Fuhong
    Zhang, Shufeng
    Deng, Guo-Jun
    ORGANIC LETTERS, 2013, 15 (07) : 1520 - 1523
  • [23] Palladium-Catalyzed Carbonylative Negishi-type Coupling of Aryl Iodides with Benzyl Chlorides
    Wu, Xiao-Feng
    Schranck, Johannes
    Neumann, Helfried
    Beller, Matthias
    CHEMISTRY-AN ASIAN JOURNAL, 2012, 7 (01) : 40 - 44
  • [24] A General Palladium-Catalyzed Carbonylative Synthesis of Chromenones from Salicylic Aldehydes and Benzyl Chlorides
    Wu, Xiao-Feng
    Wu, Lipeng
    Jackstell, Ralf
    Neumann, Helfried
    Beller, Matthias
    CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (37) : 12245 - 12248
  • [25] Palladium-catalyzed carbonylative coupling of benzyl chlorides with aryl boronic acids in aqueous media
    Wu, Xiao-Feng
    Neumann, Helfried
    Beller, Matthias
    TETRAHEDRON LETTERS, 2010, 51 (47) : 6146 - 6149
  • [26] Palladium-catalyzed Heck-carbonylation of alkene-tethered carbamoyl chlorides with aryl formates
    Chen, Chen
    Liu, Liying
    Liu, Jin-Ping
    Ding, Jie
    Ni, Chang
    Ni, Chunjie
    Zhu, Bolin
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (35) : 7129 - 7135
  • [27] Recyclable palladium-catalyzed cyclocarbonylation between benzyl chlorides and salicylic aldehydes towards coumarins
    Zhou, Yan
    Zhou, Zebiao
    Liu, Siqi
    Cai, Mingzhong
    MOLECULAR CATALYSIS, 2022, 526
  • [28] Palladium-Catalyzed Decarboxylation of Benzyl Fluorobenzoates
    Makida, Yusuke
    Matsumoto, Yasutaka
    Kuwano, Ryoichi
    SYNLETT, 2017, 28 (19) : 2573 - 2576
  • [29] Palladium-Catalyzed Difunctionalization of Norbornenes via Arylation and Alkynylation
    Shi, Yijun
    Ji, Chong-Lei
    Liu, Chengwei
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (01): : 261 - 271
  • [30] Palladium-Catalyzed Direct Alkynylation of N-Vinylacetamides
    Xu, Yun-He
    Zhang, Qiu-Chi
    He, Tao
    Meng, Fei-Fan
    Loh, Teck-Peng
    ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (07) : 1539 - 1543
12345