Palladium-Catalyzed C-H Allylation/Annulation Reaction of Amides and Allylic Alcohols: Regioselective Construction of Vinyl-Substituted 3,4-Dihydroisoquinolones

被引:6
|
作者
Wu, Haijian [1 ,2 ]
Gui, Jing [1 ,2 ]
Sun, Manman [1 ,2 ]
Ma, Yongmin [1 ,2 ]
Yang, Jianguo [1 ,2 ]
Wang, Zhiming [1 ,2 ]
机构
[1] Taizhou Univ, Adv Res Inst, Jiaojiang 318000, Zhejiang, Peoples R China
[2] Taizhou Univ, Sch Pharmaceut Sci, Jiaojiang 318000, Zhejiang, Peoples R China
来源
JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 06期
关键词
ONE-POT; ASYMMETRIC-SYNTHESIS; DIRECTING-GROUP; ALKYLATION; ALLYLATION; FUNCTIONALIZATION; ACTIVATION; ANNULATION; INDOLES; ACCESS;
D O I
10.1021/acs.joc.3c00124
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A palladium-catalyzed highly regioselective C-H allylation/annulation reaction of N-sulfonyl amides with secondary or tertiary allylic alcohols has been developed to construct 3,4-dihydroisoquinolones bearing a synthetically valuable vinyl substituent. This cascade cyclization approach of allylic alcohols involving C-H allylation has not been reported previously. The commercially available allylic alcohol substrates, the only by-product of water, and the used terminal oxidant of O2 provide environmentally benign advantages.
引用
收藏
页码:3871 / 3882
页数:12
相关论文
共 50 条
  • [1] Asymmetric Palladium-Catalyzed C-H Functionalization Cascade for Synthesis of Chiral 3,4-Dihydroisoquinolones
    Sun, Manman
    Wu, Haijian
    Xia, Xiangyu
    Chen, Weida
    Wang, Zhiming
    Yang, Jianguo
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (20): : 12835 - 12847
  • [2] Palladium-Catalyzed Regioselective C-H Functionalization/Annulation Reaction of Amides and Allylbenzenes for the Synthesis of Isoquinolinones and Pyridinones
    Zhong, Rong
    Xu, Yong
    Sun, Manman
    Wang, Yurong
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (07): : 5255 - 5264
  • [3] Palladium-Catalyzed Regioselective Aerobic Allylic C-H Oxygenation: Direct Synthesis of α,β-Unsaturated Aldehydes and Allylic Alcohols
    Li, Chunsheng
    Chen, Huoji
    Li, Jianxiao
    Li, Meng
    Liao, Jianhua
    Wu, Wanqing
    Jiang, Huanfeng
    ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (08) : 1600 - 1604
  • [4] Synthesis of Isoquinolinones via Regioselective Palladium-Catalyzed C-H Activation/Annulation
    Qi, Wenke
    Wu, Yimei
    Han, Yongxu
    Li, Yi
    CATALYSTS, 2017, 7 (11)
  • [5] Palladium-Catalyzed Direct Oxidative C-H Activation/Annulation for Regioselective Construction of N-Acylindoles
    Thombal, Raju S.
    Lee, Yong Rok
    ORGANIC LETTERS, 2020, 22 (09) : 3397 - 3401
  • [6] Palladium-Catalyzed [4+2] Annulation of Aryl and Alkenyl Carboxamides with 1,3-Dienes via C-H Functionalization: Synthesis of 3,4-Dihydroisoquinolones and 5,6-Dihydropyridinones
    Sun, Manman
    Li, Jinshan
    Chen, Weida
    Wu, Haijian
    Yang, Jianguo
    Wang, Zhiming
    SYNTHESIS-STUTTGART, 2020, 52 (08): : 1253 - 1265
  • [7] Palladium-Catalyzed Allylic C-H Oxidative Annulation for Assembly of Functionalized 2-Substituted Quinoline Derivatives
    Li, Chunsheng
    Li, Jianxiao
    An, Yanni
    Peng, Jianwen
    Wu, Wanqing
    Jiang, Huanfeng
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (24): : 12189 - 12196
  • [8] Construction of Vinyl-Substituted N-Heterocycles via Rh(III)- Catalyzed C-H Functionalization/Annulation of Pyrazolidinones
    Zhang, Shurui
    Hu, Shulei
    Wang, Kean
    Yang, Zhao
    Liu, Hong
    Wang, Jiang
    ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (02) : 238 - 243
  • [9] Synthesis of Vinyl-Substituted Dihydroisoquinolone via Ru(II)-Catalyzed C-H Functionalization/Annulation of Imidates
    Lin, Cong
    Gao, Zhenbo
    Teng, Qiuxun
    Xue, Bowen
    Li, Xiaohua
    Gao, Fei
    Shen, Liang
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2020, 40 (09) : 2863 - 2870
  • [10] Palladium-catalyzed regioselective direct C-H arylation of pyrazolo [3,4-d]pyrimidines
    El Hafi, Mohamed
    Naas, Mohammed
    Loubidi, Mohammed
    Jouha, Jabrane
    Ramli, Youssef
    Mague, Joel T.
    Essassi, El Mokhtar
    Guillaumet, Gerald
    COMPTES RENDUS CHIMIE, 2017, 20 (9-10) : 927 - 933