Accessing Furan-Linked Methylene Oxindoles/Benzofurans via Stereoselective Palladium-Catalyzed Domino Cyclization/Cycloisomerization

被引：2
|
作者：
Yi, Yujie [1 ]
Yuan, Ye [2 ]
Zhu, Songsong [3 ]
Wang, Jinbei [1 ]
Wang, Zhaolin [1 ]
Zhang, Jingli [1 ]
Gao, Guanbin [1 ,2 ]
Sun, Taolei [1 ,2 ]
机构：
[1] Wuhan Univ Technol, Sch Chem Chem Engn & Life Sci, Hubei Key Lab Nanomed Neurodegenerat Dis, Wuhan 430070, Peoples R China
[2] Wuhan Univ Technol, State Key Lab Adv Technol Mat Synth & Proc, Wuhan 430070, Peoples R China
[3] Hubei Prov Inst Food Supervis & Test, Wuhan 430075, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 17期
基金：
中国国家自然科学基金;
关键词：
EFFICIENT SYNTHESIS; 1,2-ALLENYL KETONES; CYCLIZATION; DERIVATIVES; OXINDOLE; ACIDS; ARYL;
D O I：
10.1021/acs.joc.4c00895
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A palladium-catalyzed domino cyclization/cycloisomerization reaction of alkyne-tethered carbamoyl chlorides with (E)-beta-chloroenones is reported. This reaction proceeds via a syn-carbopalladation of the alkyne, followed by a vinyl-PdII-catalyzed cycloisomerization of the (E)-beta-chloroenone cascade, which provides an efficient method to synthesize furan-linked methylene oxindoles. The reaction features stereodefined vinyl-PdII species, high to excellent 5-exo/6-endo selectivity, excellent Z/E selectivity, and the sequential formation of three bonds and bis-heterocycles. The strategy for the synthesis of furan-containing benzofurans has also been demonstrated.
引用
收藏
页码：12085 / 12093
页数：9
相关论文
共 39 条
  • [31] Facile Synthesis of Quinoline-Substituted 3-Hydroxy-2-oxindoles and 3-Amino-2-oxindoles via a Palladium-Catalyzed Cascade Intramolecular Cyclization/Intermolecular Nucleophilic Addition Reaction
    Lin, Huawei
    Hu, Xinyan
    Han, Bing
    Yang, Xianru
    Deng, Yiwei
    Luo, Jiayi
    Ge, Yanqing
    Mao, Biming
    Wang, Chang
    Yuan, Chunhao
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (05): : 3413 - 3418
  • [32] Stereoselective Synthesis of β-Alkylated α-Amino Acids via Palladium-Catalyzed Alkylation of Unactivated Methylene C(sp3)-H Bonds with Primary Alkyl Halides
    Zhang, Shu-Yu
    Li, Qiong
    He, Gang
    Nack, William A.
    Chen, Gong
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (32) : 12135 - 12141
  • [33] Rapid Access to 3-Substituted Pyridines and Carbolines via a Domino, Copper-free, Palladium-Catalyzed Sonogashira Cross-Coupling/6π-Aza Cyclization Sequence
    Uredi, Dilipkumar
    Burra, Amarender Goud
    Watkins, E. Blake
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (24): : 17748 - 17761
  • [34] Construction of Linked Nitrogen Heterocycles by Palladium(0)-Catalyzed Intramolecular Domino Cyclization of 2-Alkynylaziridines Bearing a 2-Aminoethyl Group via Ring Expansion with Isocyanate
    Okano, Akinori
    Oishi, Shinya
    Tanaka, Tetsuaki
    Fujii, Nobutaka
    Ohno, Hiroaki
    JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (10): : 3396 - 3400
  • [35] Access to N-unprotected 2-amide-substituted indoles from Ugi adducts via palladium-catalyzed intramolecular cyclization of o-iodoanilines bearing furan rings
    Peng, Hui
    Jiang, Kai
    Zhen, Guangjin
    Wang, Furong
    Yin, Biaolin
    RSC ADVANCES, 2020, 10 (20) : 11750 - 11754
  • [36] Palladium-Catalyzed Intramolecular Migratory Cycloisomerization of 3-Phenoxy Acrylic Acid Ester via C-O Bond Cleavage and C-O/C-C Bonds Formation for 2,3-Disubstituted Benzofurans Synthesis
    Kuboki, Yuichi
    Ohno, Shohei
    Sako, Makoto
    Murai, Kenichi
    Arisawa, Mitsuhiro
    CHEMICAL & PHARMACEUTICAL BULLETIN, 2023, 71 (02) : 93 - 100
  • [37] Palladium-Catalyzed Synthesis of 2,3-Disubstituted 5-Azaindoles via Heteroannulation Reaction and of 2-Substituted 5-Azaindoles through Domino Sila-Sonogashira/5-Endo Cyclization
    Livecchi, Marion
    Calvet, Geraldine
    Schmidt, Frederic
    JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (11): : 5006 - 5016
  • [38] Synthesis of Poly-Substituted Benzene from Morita-Baylis-Hillman Adducts Via [3+1+2] Annulation Strategy: Palladium-catalyzed Domino Cyclization (5-exo/3-exo), Ring-Expansion by Palladium Rearrangement, and Aromatization
    Kim, Ko Hoon
    Kim, Su Yeon
    Moon, Hye Ran
    Kim, Jae Nyoung
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2016, 37 (02): : 238 - 241
  • [39] A Domino Palladium-Catalyzed Cyclization: One-Pot Synthesis of 4b-Alkyl-10-phenyl-4b,5-dihydroindeno[2,1-a]indenes via Carbopalladation Followed by C-H Activation
    Ramesh, Karu
    Satyanarayana, Gedu
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (08): : 4254 - 4264
1234