Photoexcited Palladium-Catalyzed Synthesis of Chiral Allenes from Alkynes via Isomerization and Deracemization Sequence

被引:1
作者
Song, Changhua [1 ]
Yu, Shouyun [1 ]
机构
[1] Nanjing Univ, Chem & Biomed Innovat Ctr ChemBIC, Sch Chem & Chem Engn, State Key Lab Analyt Chem Life Sci,Jiangsu Key Lab, Nanjing 210023, Peoples R China
来源
ACS CATALYSIS | 2024年 / 14卷 / 21期
基金
中国国家自然科学基金;
关键词
alkynes; allenes; deracemization; isomerization; palladium; CYCLIZATION REACTIONS;
D O I
10.1021/acscatal.4c04956
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
A photoexcited palladium-catalyzed synthesis of chiral allenes from alkynes via a sequence of isomerization and deracemization is disclosed. This method offers an efficient and cost-effective approach to produce a wide range of chiral allenes with good enantioselectivities and yields (up to 98% yield and 99% ee). The use of readily available and stable alkynes as starting materials simplifies experimental procedures and broadens the scope of the chiral allene synthesis. DBU plays a crucial dual role in this reaction to effectively facilitate the isomerization of alkynes to allenes and enhance the palladium-catalyzed deracemization under visible light excitation, both of which are vital for the success of the process.
引用
收藏
页码:15997 / 16002
页数:6
相关论文
共 50 条
  • [21] Facile Synthesis of Polycyclic Fluorene Derivatives via a Palladium-Catalyzed Coupling, Propargyl-Allenyl Isomerization and Schmittel Cyclization Sequence
    Shen, Ruwei
    Chen, Linzhu
    Huang, Xian
    ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (17) : 2833 - 2838
  • [22] Dirhodium(II)/XantPhos Catalyzed Synthesis of β-(E)-Vinylsilanes via Hydrosilylation and Isomerization from Alkynes
    Yang, Liqun
    Yi, Mingjun
    Wu, Xiaoyu
    Lu, Yan
    Zhang, Zhaoguo
    CHEMISTRY-A EUROPEAN JOURNAL, 2024, 30 (64)
  • [23] Palladium-Catalyzed Odorless One-Pot Synthesis of Vinyl Sulfides from Organohalides, Thiourea, and Alkynes
    Feng, Jie
    Lu, Guoping
    Lv, Meifang
    Cai, Chun
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 3 (01) : 77 - 81
  • [24] Palladium-catalyzed carbonylative synthesis of substituted cyclopentenones from aryl iodides and internal alkynes
    Peng, Jin-Bao
    Wang, Wei-Feng
    Wu, Xiao-Feng
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (24) : 5882 - 5885
  • [25] Palladium-catalyzed regioselective cascade reaction of carbon dioxide, amines and allenes for the synthesis of functionalized carbamates
    Xiong, Wenfang
    Cheng, Ruixiang
    Wu, Bowen
    Wu, Wanqing
    Qi, Chaorong
    Jiang, Huanfeng
    SCIENCE CHINA-CHEMISTRY, 2020, 63 (03) : 331 - 335
  • [26] Palladium-catalyzed regioselective cascade reaction of carbon dioxide, amines and allenes for the synthesis of functionalized carbamates
    Wenfang Xiong
    Ruixiang Cheng
    Bowen Wu
    Wanqing Wu
    Chaorong Qi
    Huanfeng Jiang
    Science China Chemistry, 2020, 63 : 331 - 335
  • [27] Palladium-catalyzed regioselective cascade reaction of carbon dioxide,amines and allenes for the synthesis of functionalized carbamates
    Wenfang Xiong
    Ruixiang Cheng
    Bowen Wu
    Wanqing Wu
    Chaorong Qi
    Huanfeng Jiang
    Science China(Chemistry), 2020, 63 (03) : 331 - 335
  • [28] Synthesis of Multisubstituted Allenes via Palladium-Catalyzed Cross-Coupling Reaction of Propargyl Acetates with an Organo-aluminum Reagent
    Zhang, Zhen
    Mo, Song
    Zhang, Gang
    Shao, Xuebei
    Li, Qinghan
    Zhong, Ying
    SYNLETT, 2017, 28 (05) : 611 - 614
  • [29] Palladium-Catalyzed Asymmetric Amination of Allenyl Phosphates: Enantioselective Synthesis of Allenes with an Additional Unsaturated Unit
    Li, Qiankun
    Fu, Chunling
    Ma, Shengming
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (25) : 6511 - 6514
  • [30] Palladium-Catalyzed Annulation of Acyloximes with Arynes (or Alkynes) Synthesis of Phenanthridines and Isoquinolines
    Gerfaud, Thibaud
    Neuville, Luc
    Zhu, Jieping
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (03) : 572 - 577