Cascade Multicomponent Assemblies Involving 1,3-Enynes via Auto- Tandem Palladium Catalysis

被引:11
|
作者
He, Ze-Liang [1 ,2 ]
Zhang, Yi [1 ,2 ]
Chen, Zhi-Chao [1 ,2 ]
Du, Wei [1 ,2 ]
Chen, Ying-Chun [1 ,2 ,3 ]
机构
[1] Sichuan Univ, Key Lab Drug Targeting & Drug Delivery Syst, Educ Minist & Sichuan Prov, Chengdu 610041, Peoples R China
[2] Sichuan Univ, Sichuan Res Ctr Drug Precis Ind Technol, West China Sch Pharm, Chengdu 610041, Peoples R China
[3] Third Mil Med Univ, Coll Pharm, Chongqing 400038, Peoples R China
关键词
ENANTIOSELECTIVE SYNTHESIS; ALDEHYDES;
D O I
10.1021/acs.orglett.2c02544
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Here we report a three-component auto-tandem reaction of 1,3-enyne-tethered carbonyls, organoboronic reagents, and suitable nucleophiles catalyzed by palladium, proceeding through consecutive intramolecular vinylogous addition, Suzuki coupling, and allylic alkylation. This process exhibited high chemo-and regioselectivity with 1,3,4-trifunctionalization of the 1,3enyne motif, and a wide range of 2H-chromenes, 1,2-dihydroquinolines, benzo[b]oxepines, 1,7-annulated indoles, and other frameworks were efficiently constructed in fair to good yields and E/Z selectivity.
引用
收藏
页码:6326 / 6330
页数:5
相关论文
共 50 条
  • [41] Synthesis of Diverse Allylic Sulfone Derivatives via Sequential Hydroalkoxylation of 1,3-Enynes
    Kumar, Sourav
    Shah, Bhahwal Ali
    CHEMISTRY-A EUROPEAN JOURNAL, 2024, 30 (42)
  • [42] Palladium-Catalyzed Asymmetric Sequential Hydroamination of 1,3-Enynes: Enantioselective Syntheses of Chiral Imidazolidinones
    Li, Qiuyu
    Fang, Xinxin
    Pan, Rui
    Yao, Hequan
    Lin, Aijun
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2022, 144 (25) : 11364 - 11376
  • [43] Decarboxylative 1,4-carbocyanation of 1,3-enynes to access tetra-substituted allenes via copper/photoredox dual catalysis
    Chen, Ya
    Wang, Junjie
    Lu, Yixin
    CHEMICAL SCIENCE, 2021, 12 (34) : 11316 - 11321
  • [44] Diastereoselective 1,2-difunctionalization of 1,3-enynes enabled by merging photoexcited Hantzsch ester with chromium catalysis
    Wu, Jia
    Xu, Xiangyun
    Duan, Chongwen
    Chen, Shan
    Wang, Dan
    Fang, Likui
    Tang, Weiyang
    Li, Fusheng
    ORGANIC CHEMISTRY FRONTIERS, 2024, 11 (02) : 284 - 289
  • [45] Dialkylaluminum Hydride-Promoted Cyclodimerization of Silylated 1,3-Enynes via Skeletal Rearrangement
    Kinoshita, Hidenori
    Ishikawa, Tomoyuki
    Miura, Katsukiyo
    ORGANIC LETTERS, 2011, 13 (23) : 6192 - 6195
  • [46] A Novel Tandem Sequence to Pyrrole Syntheses by 5-endo-dig Cyclization of 1,3-Enynes with Amines
    Bharathiraja, Ganesan
    Sakthivel, Sekarpandi
    Sengoden, Mani
    Punniyamurthy, Tharmalingam
    ORGANIC LETTERS, 2013, 15 (19) : 4996 - 4999
  • [47] Tandem One-Pot Synthesis of Polysubstituted Pyridines Using the Blaise Reaction Intermediate and 1,3-Enynes
    Chun, Yu Sung
    Lee, Jun Hee
    Kim, Ju Hyun
    Ko, Young Ok
    Lee, Sang-gi
    ORGANIC LETTERS, 2011, 13 (24) : 6390 - 6393
  • [48] Palladium-Catalyzed Modular and Enantioselective cis-Difunctionalization of 1,3-Enynes with Imines and Boronic Reagents
    He, Qing
    Zhu, Lei
    Yang, Zhen-Hong
    Zhu, Bo
    Ouyang, Qin
    Du, Wei
    Chen, Ying-Chun
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (43) : 17989 - 17994
  • [49] Palladium-catalyzed four-component domino sulfonylation and carbonylation of 1,3-enynes at room temperature
    Wang, Jing
    Ying, Jun
    ORGANIC CHEMISTRY FRONTIERS, 2024, 11 (20): : 5851 - 5858
  • [50] Synthesis of Spirolactones via a BF3•Et2O-Promoted Cascade Annulation of α-Keto Acids and 1,3-Enynes
    Zhao, Beibei
    Zhang, Zhen
    Li, Pinhua
    Miao, Tao
    Wang, Lei
    ORGANIC LETTERS, 2021, 23 (15) : 5698 - 5702