Rhodium(III)-Catalyzed C-H Alkenylation/Directing Group Migration for the Regio- and Stereoselective Synthesis of Tetrasubstituted Alkenes

被引：40
|
作者：
Wu, Xiaowei [1 ,2 ]
Lu, Yangbin [3 ,4 ]
Qiao, Jin [3 ]
Dai, Wenhao [5 ]
Jia, Xiuwen [1 ]
Ni, Hangcheng [3 ]
Zhang, Xiaoning [3 ]
Liu, Hong [5 ]
Zhao, Fei [1 ,3 ]
机构：
[1] Chengdu Univ, Sichuan Ind Inst Antibiot, Antibiot Res & Reevaluat Key Lab Sichuan Prov, Chengdu 610052, Peoples R China
[2] Baylor Coll Med, Dept Pharmacol & Chem Biol, Houston, TX 77030 USA
[3] Chengdu Univ, Sichuan Ind Inst Antibiot, Jinhua Branch, Jinhua 321007, Zhejiang, Peoples R China
[4] Chinese Acad Sci, Shanghai Inst Mat Med, Key Lab Drug Res, Shanghai 201203, Peoples R China
[5] Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China
来源：
ORGANIC LETTERS | 2020年 / 22卷 / 23期
基金：
中国国家自然科学基金;
关键词：
BOND FORMATION; N-PHENOXYACETAMIDES; EFFICIENT ACCESS; INTERNAL ALKYNES; DIRECT ADDITION; DIRECTING GROUP; INDOLES; OLEFINATION; HYDROARYLATION; ARENES;
D O I：
10.1021/acs.orglett.0c03077
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient Rh(III)-catalyzed C-H alkenylation/directing group migration cascade between indoles and alkynes for the assembly of tetrasubstituted alkenes is reported. The carbamoyl directing group migrates to the carbon of the alkene moiety of the products through rare Rh-catalyzed C-N bond cleavage after the C-H alkenylation step and thus acts as an internal amidation reagent. This protocol shows broad substrate scope, excellent regio/stereoselectivity, and good to excellent yields.
引用
收藏
页码：9163 / 9168
页数：6
相关论文
共 50 条
  • [21] Rhodium(III)-catalyzed regio- and stereoselective benzylic α-fluoroalkenylation with gem-difluorostyrenes
    Kong, Lingheng
    Liu, Bingxian
    Zhou, Xukai
    Wang, Fen
    Li, Xingwei
    CHEMICAL COMMUNICATIONS, 2017, 53 (74) : 10326 - 10329
  • [22] Iridium-Catalyzed Benzylamine C-H Alkenylation Enabled by Pentafluorobenzoyl as the Directing Group
    Yang, Xiao
    Sun, Rui
    Zhang, Chunchun
    Zheng, Xueli
    Yuan, Maolin
    Fu, Haiyan
    Li, Ruixiang
    Chen, Hua
    ORGANIC LETTERS, 2019, 21 (04) : 1002 - 1006
  • [23] Ruthenium(II)-Catalyzed Regio- and Stereoselective C-H Allylation of Indoles with Allyl Alcohols
    Wu, Xiaowei
    Ji, Haitao
    ORGANIC LETTERS, 2018, 20 (08) : 2224 - 2227
  • [24] Rhodium-Catalyzed C4-Selective C-H Alkenylation of 2-Pyridones by Traceless Directing Group Strategy
    Hazra, Sunit
    Hirano, Koji
    Miura, Masahiro
    ORGANIC LETTERS, 2021, 23 (04) : 1388 - 1393
  • [25] Introducing the Chiral Transient Directing Group Strategy to Rhodium(III)-Catalyzed Asymmetric C-H Activation
    Li, Guozhu
    Jiang, Jijun
    Xie, Hui
    Wang, Jun
    CHEMISTRY-A EUROPEAN JOURNAL, 2019, 25 (18) : 4688 - 4694
  • [26] Rhodium(III)-Catalyzed Meta-Selective C-H Alkenylation of Phenol Derivatives
    Mi, Rui-Jie
    Sun, Yong-Zhen
    Wang, Jing-Yun
    Sun, Jing
    Xu, Zhaoqing
    Zhou, Ming-Dong
    ORGANIC LETTERS, 2018, 20 (17) : 5126 - 5129
  • [27] Rhodium(III)-catalyzed C7-position C-H alkenylation and alkynylation of indolines
    Yang, Xiao-Fei
    Hu, Xu-Hong
    Feng, Chao
    Loh, Teck-Peng
    CHEMICAL COMMUNICATIONS, 2015, 51 (13) : 2532 - 2535
  • [28] Highly stereoselective synthesis of tetrasubstituted alkenes via hydroamination of alkynes and C-H acetoxylation
    Liu, Weibing
    Chen, Cui
    Zhang, Qing
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (19) : 6484 - 6486
  • [29] Photoredox-Catalyzed C-H Arylation of Internal Alkenes to Tetrasubstituted Alkenes: Synthesis of Tamoxifen
    Wang, Quannan
    Yang, Xiaoge
    Wu, Ping
    Yu, Zhengkun
    ORGANIC LETTERS, 2017, 19 (22) : 6248 - 6251
  • [30] Nondirected C-H Alkenylation of Arenes with Alkenes under Rhodium Catalysis
    Ghosh, Koushik
    Mihara, Gen
    Nishii, Yuji
    Miura, Masahiro
    CHEMISTRY LETTERS, 2019, 48 (02) : 148 - 151
12345