Dual Photoredox/Nickel-Catalyzed Dehydrative Difluoroalkylation of Benzyl Alcohols for the Synthesis of Allylic gem-Difluorides

被引:2
|
作者
Bai, Yuyang [1 ]
Cao, Liping [1 ]
Li, Siyuan [2 ,3 ]
Zhang, Guang'an [2 ,3 ]
Liu, Yingguo [1 ]
Zhao, Fengqian [2 ,3 ]
Wu, Junliang [2 ,3 ]
机构
[1] Zhengzhou Univ, Henan Inst Adv Technol, Zhengzhou 450001, Peoples R China
[2] Zhengzhou Univ, Green Catalysis Ctr, Zhengzhou 450001, Peoples R China
[3] Zhengzhou Univ, Coll Chem, Zhengzhou 450001, Peoples R China
关键词
ALKENES; ALKYNES; FLUORINE;
D O I
10.1021/acs.orglett.3c02248
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A photoredox/Lewis acid cooperative catalytic system has been developed for the construction of C-vinyl-C-Rf bonds through the dehydrative difluoroalkylation of benzyl alcohols. A variety of allylic gem-difluorides could be obtained in moderate yields with good to excellent E/Z selectivity. In addition, several control experiments have been explored, and a possible mechanism was proposed for this process.
引用
收藏
页码:6511 / 6516
页数:6
相关论文
共 50 条
  • [21] Nickel-Catalyzed Redox-Economical Coupling of Alcohols and Alkynes to Form Allylic Alcohols
    Nakai, Kenichiro
    Yoshida, Yuji
    Kurahashi, Takuya
    Matsubara, Seijiro
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (22) : 7797 - 7800
  • [22] Synthesis of gem-Difluoroalkenes via Nickel-Catalyzed Allylic Defluorinative Reductive Cross-Coupling
    Lan, Yun
    Yang, Feiyan
    Wang, Chuan
    ACS CATALYSIS, 2018, 8 (10): : 9245 - 9251
  • [23] Dual Photoredox/Nickel-Catalyzed Three-Component Carbofunctionalization of Alkenes
    Garcia-Dominguez, Andres
    Mondal, Rahul
    Nevado, Cristina
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (35) : 12286 - 12290
  • [24] Nickel-catalyzed cross-electrophile coupling of aryl chlorides with allylic alcohols
    Yu, Hang
    Wang, Zhong-Xia
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (44) : 9723 - 9731
  • [25] Neutral nickel-catalyzed dehydrosulfonylation of unactivated allylic alcohols under mild conditions
    Yang, Yahui
    Zhu, Haibo
    Gong, Bozhen
    Yang, Hong
    Fan, Qiangwen
    Le, Zhang-Gao
    Xie, Zongbo
    CHEMICAL COMMUNICATIONS, 2024, 60 (18) : 2516 - 2519
  • [26] Nickel-Catalyzed Enantioselective Alkylative Coupling of Alkynes and Aldehydes: Synthesis of Chiral Allylic Alcohols with Tetrasubstituted Olefins
    Yang, Yun
    Zhu, Shou-Fei
    Zhou, Chang-Yue
    Zhou, Qi-Lin
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (43) : 14052 - +
  • [27] Photoredox/Nickel Dual-Catalyzed Allylation of Aldehydes with Allylic Alcohols and Mechanistic Insights in the Presence of CO2
    Zhang, Zeyu
    Han, Zongchang
    Li, Jiayuan
    Hu, Han-Shi
    Li, Jun
    Xi, Chanjuan
    ACS CATALYSIS, 2024, 14 (16): : 12392 - 12402
  • [28] Fluorinative Rearrangement Involving Cleavage and Recombination of Carbon-Fluorine Bond: Synthesis of Functionalized Allylic gem-Difluorides from Propargylic Fluorides
    Ni, Chuanfa
    Hu, Jinbo
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2020, 40 (09) : 2997 - 2998
  • [29] Synthesis of Hexafluoroisopropyl Aryl Ethers via Dual Photoredox/Nickel-Catalyzed C-O Coupling
    He, Xu
    Zhang, Yu-Yang
    Shou, Jia-Yi
    Chu, Lingling
    Qing, Feng-Ling
    ORGANIC LETTERS, 2024, 26 (31) : 6782 - 6786
  • [30] Dual photoredox nickel-catalyzed silylation of aryl/heteroaryl bromides using hydrosilanes
    Liu, Shuai
    Robert, Frederic
    Landais, Yannick
    CHEMICAL COMMUNICATIONS, 2023, 59 (76) : 11369 - 11372