Highly Enantioselective Cross-Electrophile Aryl-Alkenylation of Unactivated Alkenes

被引:178
作者
Tian, Zhi-Xiong [1 ]
Qiao, Jin-Bao [1 ]
Xu, Guang-Li [1 ]
Pang, Xiaobo [1 ]
Qi, Liangliang [1 ]
Ma, Wei-Yuan [1 ]
Zhao, Zhen-Zhen [1 ]
Duan, Jicheng [1 ]
Du, Yun-Fei [1 ]
Su, Peifeng [1 ]
Liu, Xue-Yuan [1 ]
Shu, Xing-Zhong [1 ]
机构
[1] Lanzhou Univ, Coll Chem & Chem Engn, SKLAOC, 222 South Tianshui Rd, Lanzhou 730000, Peoples R China
基金
中国国家自然科学基金;
关键词
PALLADIUM-CATALYZED 1,4-DIFUNCTIONALIZATION; COUPLING REACTIONS; REDUCTIVE DICARBOFUNCTIONALIZATION; NICKEL; HALIDES; DIFUNCTIONALIZATION; CONSTRUCTION; CYCLIZATION; ALKYLATION; ALLYLATION;
D O I
10.1021/jacs.9b03863
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Enantioselective cross-electrophile reactions remain a challenging subject in metal catalysis, and with respect to data, studies have mainly focused on stereoconvergent reactions of racemic alkyl electrophiles. Here, we report an enantioselective cross-electrophile aryl-alkenylation reaction of unactivated alkenes. This method provides access to a number of biologically important chiral molecules such as dihydrobenzofurans, indolines, and indanes. The incorporated alkenyl group is suitable for further reactions that can lead to an increase under mild conditions at room temperature, and an easily accessible chiral pyrox ligand is used to afford products with high enantioselectivity. The synthetic utility of this method is demonstrated by enabling the modification of complex molecules such as peptides, indometacin, and steroids.
引用
收藏
页码:7637 / 7643
页数:7
相关论文
共 50 条
  • [41] Palladium-Catalyzed Cross-Electrophile Couplings of Aryl Thianthrenium Salts with Aryl Bromides via C-S Bond Activation
    Fu, Qian-Qian
    Liang, Yuan
    Sun, Xiao-Xiao
    Chu, Xue-Qiang
    Xu, Hao
    Zhou, Xiaocong
    Rao, Weidong
    Shen, Zhi-Liang
    [J]. ORGANIC LETTERS, 2024, 26 (40) : 8577 - 8582
  • [42] Amine-Borane-Mediated, Nickel/Photoredox-Catalyzed Cross-Electrophile Coupling between Alkyl and Aryl Bromides
    Li, Ke-Rong
    He, Xian-Chen
    Gao, Jie
    Liu, Yan-Ling
    Chen, Hong-Bin
    Xiang, Hao-Yue
    Chen, Kai
    Yang, Hua
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (17) : 12658 - 12667
  • [43] Cross-Electrophile Coupling between Aryl/Vinyl Triflates and Vinyl Tosylates for the Synthesis of gem-Difluoroalkenes via Ni/Pd Cooperative Catalysis
    Xiong, Baojian
    Li, Yue
    Zhang, Jinyu
    Liu, Jiangjun
    Zhang, Xuemei
    Lian, Zhong
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (05) : 1009 - 1015
  • [44] Late-Stage Cross-Electrophile Coupling of Arylthianthrenium Salts with (Hetero)aryl (Pseudo)halides via Palladium Catalysis
    Xie, Yuanhao
    Zhang, Li
    Ritter, Tobias
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2025,
  • [45] Ni-catalyzed cross-electrophile coupling between vinyl/aryl and alkyl sulfonates: synthesis of cycloalkenes and modification of peptides
    Duan, Jicheng
    Du, Yun-Fei
    Pang, Xiaobo
    Shu, Xing-Zhong
    [J]. CHEMICAL SCIENCE, 2019, 10 (37) : 8706 - 8712
  • [46] RETRACTED: Deoxygenative cross-electrophile coupling of benzyl chloroformates with aryl iodides (Retracted article. See JUL, 2023)
    Pan, Yingying
    Gong, Yuxin
    Song, Yanhong
    Tong, Weiqi
    Gong, Hegui
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (17) : 4230 - 4233
  • [47] Palladium-Catalyzed Cross-Electrophile Coupling between Aryl Diazonium Salt and Aryl Iodide/Diaryliodonium Salt in H2O-EtOH
    Manna, Kartic
    Jana, Ranjan
    [J]. ORGANIC LETTERS, 2023, : 341 - 346
  • [48] Development of Photoredox Cross-Electrophile Coupling of Strained Heterocycles with Aryl Bromides Using High-Throughput Experimentation for Library Construction
    Mori, Yukiko
    Hayashi, Mutsuyo
    Sato, Ryuma
    Tai, Kuninori
    Nagase, Tsuyoshi
    [J]. ORGANIC LETTERS, 2023, 25 (30) : 5569 - 5573
  • [49] Mechanical metal activation for Ni-catalyzed, Mn-mediated cross-electrophile coupling between aryl and alkyl bromides
    Wu, Sisi
    Shi, Weijia
    Zou, Gang
    [J]. NEW JOURNAL OF CHEMISTRY, 2021, 45 (25) : 11269 - 11274
  • [50] Nickel-Catalyzed Cross-Electrophile Coupling between Benzyl Alcohols and Aryl Halides Assisted by Titanium Co-reductant
    Suga, Takuya
    Ukaji, Yutaka
    [J]. ORGANIC LETTERS, 2018, 20 (24) : 7846 - 7850