Palladium-Catalyzed C(sp3) C(sp2) Cross-Coupling of (Trimethylsilyl)methyllithium with (Hetero)Aryl Halides

被引：29
|
作者：
Heijnen, Dorus [1 ]
Hornillos, Valentin [1 ]
Corbet, Brian P. [1 ]
Giannerini, Massimo [1 ]
Feringa, Ben L. [1 ]
机构：
[1] Univ Groningen, Stratingh Inst Chem, NL-9747 AG Groningen, Netherlands
来源：
ORGANIC LETTERS | 2015年 / 17卷 / 09期
基金：
欧洲研究理事会;
关键词：
CARBON BOND FORMATION; GRIGNARD-REAGENTS; ORGANIC HALIDES; ORGANOLITHIUM COMPOUNDS; EFFICIENT SYNTHESIS; SELECTIVE SYNTHESIS; ARYL DERIVATIVES; METAL; ALKENYL; ALKYL;
D O I：
10.1021/acs.orglett.5b00905
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The palladium-catalyzed direct cross-coupling of a range of organic chlorides and bromides with the bifunctional C(sp(3))-(trimethylsilyl)methyllithium reagent is reported. The use of Pd-PEPPSI-IPent as the catalyst allows for the preparation of structurally diverse and synthetically versatile benzyl- and allylsilanes in high yields under mild conditions (room temperature) with short reaction times.
引用
收藏
页码：2262 / 2265
页数：4
相关论文
共 50 条
  • [1] Palladium-Catalyzed C(sp3)-Si Bonds Transformation for Constructing Trifluoropropyl (Hetero)arenes through C(sp3)-C(sp2) Cross-Coupling Reactions
    Liu Junjun
    Lu Taotao
    Ma Ping
    Zhao Qingyang
    Yee, Kwong Fuk
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2024, 44 (04) : 1319 - 1326
  • [2] Palladium-Catalyzed Intramolecular Cross-Coupling of Unactivated C(sp3)-H and C(sp2)-H Bonds
    Wu, Zhuo
    Wu, Zechen
    Sun, Xueliang
    Qi, Weixin
    Zhang, Zhengyang
    Zhang, Yanghui
    [J]. ORGANIC LETTERS, 2021, 23 (18) : 7161 - 7165
  • [3] Synthesis of Arylethylamines via C(sp3)-C(sp3) Palladium-Catalyzed Cross-Coupling
    Lippa, Rhys A.
    Battersby, David J.
    Murphy, John A.
    Barrett, Tim N.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (04): : 3583 - 3604
  • [4] Ni/Photoredox-Catalyzed C(sp2)-C(sp3) Cross-Coupling of Alkyl Pinacolboronates and (Hetero)Aryl Bromides
    Cauley, Anthony N.
    Ramirez, Antonio
    Barhate, Chandan L.
    Donnell, Andrew F.
    Khandelwal, Purnima
    Sezen-Edmonds, Melda
    Sherwood, Trevor C.
    Sloane, Jack L.
    Cavallaro, Cullen L.
    Simmons, Eric M.
    [J]. ORGANIC LETTERS, 2022, 24 (31) : 5663 - 5668
  • [5] Palladium-catalyzed C(sp3)-C(sp2) coupling: synthesis of C(3)-arylphthalides
    Rao, H. Surya Prakash
    Prabhakaran, J.
    [J]. CHEMICAL PAPERS, 2024, : 5985 - 5991
  • [6] Silacyclization through palladium-catalyzed intermolecular silicon-based C(sp2)-C(sp3) cross-coupling
    Qin, Ying
    Li, Lianghui
    Liang, Jin-Yuan
    Li, Kailong
    Zhao, Dongbing
    [J]. CHEMICAL SCIENCE, 2021, 12 (42) : 14224 - 14229
  • [7] Palladium-catalyzed C(sp3)-Si cross-coupling silylation of benzyl halides with hydrosilanes
    Zhou, Xiao-Hua
    Zhu, Jun-Hui
    Song, Guang-Ao
    Jiang, Xin-Li
    Fang, Xiao-Jun
    Xu, Zheng
    Xu, Li-Wen
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (21) : 5443 - 5450
  • [8] Cobalt-NHC Catalyzed C(sp2)-C(sp3) and C(sp2)-C(sp2) Kumada Cross-Coupling of Aryl Tosylates with Alkyl and Aryl Grignard Reagents
    Piontek, Aleksandra
    Ochedzan-Siodlak, Wioletta
    Bisz, Elwira
    Szostak, Michal
    [J]. CHEMCATCHEM, 2021, 13 (01) : 202 - 206
  • [9] Palladium-catalyzed a-arylation of nitroalkanes with aryl triflates through the C(sp2)-C(sp3) bond coupling
    Hu, Sengui
    He, Xiaoyu
    Lei, Zhiguo
    Yu, Lin
    Duan, Wengui
    [J]. JOURNAL OF MOLECULAR STRUCTURE, 2023, 1286
  • [10] Iron-Catalyzed C(sp2)-C(sp3) Cross-Coupling of Aryl Chlorobenzoates with Alkyl Grignard Reagents
    Bisz, Elwira
    Szostak, Michal
    [J]. MOLECULES, 2020, 25 (01):
12345