Catalytic site-specific and regioselective (3+2) transannulations between 1,2,3-thiadiazoles and allenoates

被引：8
作者：
Chen, Cunzhi [1 ]
Fang, Shuyan [1 ]
Yu, Mingwu [2 ]
Xu, Jiaxi [1 ]
Yang, Zhanhui [1 ]
机构：
[1] Beijing Univ Chem Technol, Coll Chem, Dept Organ Chem, Beijing 100029, Peoples R China
[2] Ludong Univ, Sch Chem & Mat Sci, Yantai 264025, Shandong, Peoples R China
来源：
ORGANIC CHEMISTRY FRONTIERS | 2023年 / 10卷 / 03期
基金：
中国国家自然科学基金;
关键词：
ALKENES; ALLENES;
D O I：
10.1039/d2qo01662a
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Allenoates, a type of perpendicularly "strained" surrogate of alkynes, readily transannulate, site-specifically and regio-selectively, with 1,2,3-thiadiazoles in the presence of catalytic Rh(i)/bisphosphine, producing tetrasubstituted thiophenes in a redox-neutral manner. 1,2,3-Thiadiazoles act as masked 1,3-dipoles with nucleophilic sulfur and electrophilic carbon termini.
引用
收藏
页码：661 / 667
页数：7
相关论文
共 29 条
  • [11] Synthesis of Substituted Coumarins via Bronsted Acid Mediated Condensation of Allenes with Substituted Phenols or Anisoles
    Kim, Sundae
    Kang, Dongjin
    Lee, Chang-Hee
    Lee, Phil Ho
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (15) : 6530 - 6537
  • [12] Rhodium Thiavinyl Carbenes from 1,2,3-Thiadiazoles Enable Modular Synthesis of Multisubstituted Thiophenes
    Kurandina, Dania
    Gevorgyan, Vladimir
    [J]. ORGANIC LETTERS, 2016, 18 (08) : 1804 - 1807
  • [13] Thioamide synthesis via copper-catalyzed C-H activation of 1,2,3-thiadiazoles enabled by slow release and capture of thioketenes
    Lu, Changhui
    Li, Xiaohong
    Chang, Shunqin
    Zhang, Yuqi
    Xing, Donghui
    Wang, Shuo
    Lin, Yueping
    Jiang, Huanfeng
    Huang, Liangbin
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (09) : 2382 - 2389
  • [14] Mechanistic insights into the Rh(i)-catalyzed transannulation of 1,2,3-thiadiazoles with alkenes, alkynes, and nitriles: Does the intermediacy of α-thiavinyl Rh-carbenoids play an important role?
    Lv, Kang
    Bao, Xiaoguang
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (02): : 310 - 318
  • [15] Some typical advances in the synthetic applications of allenes
    Ma, SM
    [J]. CHEMICAL REVIEWS, 2005, 105 (07) : 2829 - 2871
  • [16] Progress in Synthesis of Conductive Polymer Poly(3,4-Ethylenedioxythiophene)
    Nie, Shisong
    Li, Zaifang
    Yao, Yuyuan
    Jin, Yingzhi
    [J]. FRONTIERS IN CHEMISTRY, 2021, 9
  • [17] Thiophene Syntheses by Ring Forming Multicomponent Reactions
    Schaper, Klaus
    Mueller, Thomas J. J.
    [J]. TOPICS IN CURRENT CHEMISTRY, 2018, 376 (05)
  • [18] Synthesis of Bicyclic Isothiazoles through an Intramolecular Rhodium-Catalyzed Transannulation of Cyanothiadiazoles
    Seo, Boram
    Kim, Hyunseok
    Kim, Ya Gob
    Baek, Yonghyeon
    Urn, Kyusik
    Lee, Phil Ho
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (19) : 10574 - 10582
  • [19] Synthesis of Isothiazole via the Rhodium-Catalyzed Transannulation of 1,2,3-Thiadiazoles with Nitriles
    Seo, Boram
    Kim, Ya Gob
    Lee, Phil Ho
    [J]. ORGANIC LETTERS, 2016, 18 (19) : 5050 - 5053
  • [20] Thiophene derivatives: A potent multitargeted pharmacological scaffold
    Singh, Atamjit
    Singh, Gurvinder
    Bedi, Preet Mohinder Singh
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 2020, 57 (07) : 2658 - 2703
123