Rhodium-Catalyzed Intramolecular Cyclization to Synthesize 2-Aminobenzofurans via Carbene Metathesis Reactions

被引：3
|
作者：
Li, Xue [1 ,2 ]
Sheng, Heyun [1 ,2 ]
Song, Qiuling [1 ,2 ,3 ,4 ]
机构：
[1] Huaqiao Univ, Coll Chem Engn, Inst Next Generat Matter Transformat, Xiamen 361021, Fujian, Peoples R China
[2] Huaqiao Univ, Coll Mat Sci Engn, Xiamen 361021, Fujian, Peoples R China
[3] Fuzhou Univ, Coll Chem, Key Lab Mol Synth & Funct Discovery Fijian Prov Un, Fuzhou 350108, Fujian, Peoples R China
[4] Henan Normal Univ, Sch Chem & Chem Engn, Xinxiang 453007, Henan, Peoples R China
来源：
ORGANIC LETTERS | 2023年 / 25卷 / 12期
基金：
中国国家自然科学基金;
关键词：
ALKYNES; ACCESS; INSERTION; CYCLOADDITION; CASCADES; TRANSANNULATION; CYCLOPROPENES; CONSTRUCTION; DERIVATIVES; BENZOFURAN;
D O I：
10.1021/acs.orglett.3c00539
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Herein, we report a new method of synthesizing of 2-aminobenzofuran 3-enes via the formal C-S insertion reaction of alkyne-tethered diazo compounds. Metal carbene, as a kind of active synthetic intermediate, plays a very important role in organic synthesis. Through the carbene/alkyne metathesis strategy, a new donor carbene is produced in situ as a key intermediate, which has different reactions from the donor receptor carbene.
引用
收藏
页码：2113 / 2117
页数：5
相关论文
共 50 条
  • [1] Rhodium-catalyzed intramolecular cyclization for synthesizing thiodihydropyrans
    Wang, Yunxiao
    Xu, Ze-Feng
    Chen, Jing
    Yu, Mingming
    Guo, Sheng-Rong
    Li, Chuan-Ying
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (33) : 6695 - 6698
  • [2] Recent Advances in Rhodium-Catalyzed Cyclization Reactions
    Iwao Ojima
    Andrew C. Moralee
    Victor C. Vassar
    Topics in Catalysis, 2002, 19 : 89 - 99
  • [3] Recent advances in rhodium-catalyzed cyclization reactions
    Ojima, I
    Moralee, AC
    Vassar, VC
    TOPICS IN CATALYSIS, 2002, 19 (01) : 89 - 99
  • [4] The Rhodium-Catalyzed Carbene Cyclization Cycloaddition Cascade Reaction of Vinylsulfonates
    Shi, Bairu
    Merten, Sandra
    Wong, David K. Y.
    Chu, John C. K.
    Liu, Lok Lok
    Lam, Sze Kui
    Jaeger, Anne
    Wong, Wing-Tak
    Chiu, Pauline
    Metz, Peter
    ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (18) : 3128 - 3132
  • [5] Divergent Rhodium-Catalyzed Cyclization Reactions of Enoldiazoacetamides with Nitrosoarenes
    Cheng, Qing-Qing
    Lankelma, Marianne
    Wherritt, Daniel
    Arman, Hadi
    Doyle, Michael P.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (29) : 9839 - 9842
  • [6] Rhodium-Catalyzed Carbene Transfer Reactions for Sigmatropic Rearrangement Reactions of Selenium Ylides
    Jana, Sripati
    Koenigs, Rene M.
    ORGANIC LETTERS, 2019, 21 (10) : 3653 - 3657
  • [7] Rhodium-Catalyzed Enantioselective Cyclization of 2-Allenylbenzoxazoles
    Becker, Antonia
    Bauer, Felix
    Breit, Bernhard
    ORGANIC LETTERS, 2024, 26 (12) : 2451 - 2455
  • [8] Rhodium-Catalyzed Cyclization Reactions of γ-Alkynyl Aldehydes with Carboxylic Acid Anhydrides
    Tajima, Yuki
    Kobayashi, Masayuki
    Noguchi, Keiichi
    Tanaka, Ken
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (24) : 5266 - 5271
  • [9] Synthesis of Siloles via Rhodium-Catalyzed Cyclization of Alkynes and Diynes with Hexamethyldisilane
    Matsuda, Takanori
    Suda, Yuya
    Fujisaki, Yosuke
    SYNLETT, 2011, (06) : 813 - 816
  • [10] Rhodium-catalyzed carbene transfer to alkynes via 2-furylcarbenes generated from enynones
    Gonzalez, Maria J.
    Lopez, Enol
    Vicente, Ruben
    CHEMICAL COMMUNICATIONS, 2014, 50 (40) : 5379 - 5381
12345