Switchable Decarboxylative Heck-Type Reaction and Oxo-alkylation of Styrenes with N-Hydroxyphthalimide Esters under Photocatalysis

被引：58
|
作者：
Xia, Zi-Hao [1 ,2 ]
Zhang, Chun-Lin [1 ]
Gao, Zhong-Hua [1 ,2 ]
Ye, Song [1 ,2 ]
机构：
[1] Chinese Acad Sci, Beijing Natl Lab Mol Sci, Key Lab Mol Recognit & Funct, CAS Res Educ Ctr Excellence Mol Sci,Inst Chem, Beijing 100190, Peoples R China
[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China
来源：
ORGANIC LETTERS | 2018年 / 20卷 / 12期
基金：
中国国家自然科学基金;
关键词：
REDOX-ACTIVE ESTERS; CARBOXYLIC-ACIDS; ARYL; N-(ACYLOXY)PHTHALIMIDES; ALKENYLATION; BROMIDES; HALIDES; KETONES; FUNCTIONALIZATION; PALLADATION;
D O I：
10.1021/acs.orglett.8b01268
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The switchable visible-light-mediated decarboxylative Heck-type reaction and oxo-alkylation reaction of N-hydroxyphthalimide esters under photocatalysis were developed. Disubstituted or trisubstituted alkenes were obtained in good yield with high E-selectivity in the presence of Bronsted acid as the additive, while ketones resulted in the absence of the acidic additive.
引用
收藏
页码：3496 / 3499
页数：4
相关论文
共 9 条
  • [1] Photocatalytic decarboxylative alkylation of electron-rich heteroarenes with alkyl N-hydroxyphthalimide esters
    Hu, Han -Wei
    Zhang, Cairong
    Yang, Yu-Ming
    Deng, Hai-Qiang
    Tang, Zhen-Yu
    TETRAHEDRON LETTERS, 2022, 103
  • [2] Visible-Light-Induced Regioselective Alkylation of Coumarins via Decarboxylative Coupling with N-Hydroxyphthalimide Esters
    Jin, Can
    Yan, Zhiyang
    Sun, Bin
    Yang, Jin
    ORGANIC LETTERS, 2019, 21 (07) : 2064 - 2068
  • [3] Photoredox-catalyzed stereoselective alkylation of enamides with N-hydroxyphthalimide esters via decarboxylative cross-coupling reactions
    Guo, Jing-Yu
    Zhang, Ze-Yu
    Guan, Ting
    Mao, Lei-Wen
    Ban, Qian
    Zhao, Kai
    Loh, Teck-Peng
    CHEMICAL SCIENCE, 2019, 10 (38) : 8792 - 8798
  • [4] A Visible Light-Driven Minisci-Type Reaction with N-Hydroxyphthalimide Esters
    Kammer, Lisa Marie
    Rahman, Aliyaah
    Opatz, Till
    MOLECULES, 2018, 23 (04):
  • [5] Photo-induced decarboxylative coupling reaction between aliphatic N-hydroxyphthalimide esters and terminal 2-trifluoromethylalkenes
    Chen, Man
    Wang, Chaoyu
    Xie, Lang
    Mao, Ting
    Xiao, Long
    Wang, Ze
    Han, Wen-Yong
    Liu, Ping
    Jia, Jia
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2025, 23 (10) : 2445 - 2449
  • [6] Metal-Free Regioselective Alkylation of Imidazo[1,2-a]pyridines with N-Hydroxyphthalimide Esters under Organic Photoredox Catalysis
    Sun, Bin
    Xu, Tengwei
    Zhang, Liang
    Zhu, Rui
    Yang, Jin
    Xu, Min
    Jin, Can
    SYNLETT, 2020, 31 (04) : 363 - 368
  • [7] Radical C(sp3)-H Heck-type Reaction of N-Alkoxybenzimidoyl Chlorides with Styrenes to Construct Alkenols
    Fang, Di
    Zhang, Yidan
    Chen, Yiyun
    ORGANIC LETTERS, 2022, 24 (10) : 2050 - 2054
  • [8] Visible-Light-Induced C2 Alkylation of Heterocyclic N-Oxides with N-Hydroxyphthalimide Esters under Metal-Free Conditions
    Qin, Pi-Tao
    Sun, Jing
    Wang, Fei
    Wang, Jing-Yun
    Wang, He
    Zhou, Ming-Dong
    ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (21) : 4707 - 4715
  • [9] Visible-Light-Promoted Electron Donor-Acceptor Complex Enabled Decarboxylative Alkylation of Quinoxalin-2(1H)-ones and N-Hydroxyphthalimide Esters with Na2S as a Catalytic Donor
    Song, Hai-Yang
    Zhang, Zhuo-Tao
    Tan, Hong-Yu
    Lu, Yu-Han
    Yang, Tian-Bao
    Chen, Jin-Yang
    Ji, Hong-Tao
    He, Wei-Min
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 12 (02)
1