2,3-disubstituted benzo[b]thiophenes from diarylalkynes via electrophilic addition-cyclization and palladium-catalyzed cross-coupling

被引：19
|
作者：
Lamanna, Giuseppe [1 ]
Menichetti, Stefano [1 ]
机构：
[1] Univ Florence, Lab Progettaz Sintesi & Studio Eterocicli Biol At, I-50019 Sesto Fiorentino, FI, Italy
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2007年 / 349卷 / 13期
关键词：
benzo[b]thiophenes; cross-coupling; electrophilic addition; electrophilic substitution; phthalimidesulfenyl chloride; solid phase synthesis; DIRECTED THROMBIN INHIBITORS; ONE-POT SYNTHESIS; ARYL; DERIVATIVES; ANTIESTROGENS; PRECATALYST; CHLORIDES; NHC;
D O I：
10.1002/adsc.200700172
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
Diarylalkynes are readily transformed in 3-chlorobenzo[b]thiophenes in a two-step electrophilic addition-cyclization procedure that runs highly efficiently in solution or in the solid phase. The heteroaromatic carbon-chlorine bond participates in palladium-catalyzed Suzuki-Miyaura or Buchwald-Hartwig cross-couplings to give, in a single step, 2,3-disubstituted derivatives of pharmacological relevance.
引用
收藏
页码：2188 / 2194
页数：7
相关论文
共 50 条
  • [41] An efficient route to regioselective functionalization of benzo[b]thiophenes via palladium-catalyzed decarboxylative Heck coupling reactions: insights from experiment and computation
    Yang, Daoshan
    Liu, Yuxia
    Sun, Pengfei
    Zhang, Ning
    Wei, Wei
    Sun, Mingyang
    Chen, Guang
    Bi, Siwei
    Wang, Hua
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (03) : 895 - 904
  • [42] One-Pot and Regiospecific Synthesis of 2,3-Disubstituted Indoles from 2-Bromoanilides via Consecutive Palladium-Catalyzed Sonogashira Coupling, Amidopalladation, and Reductive Elimination
    Lu, Bruce Z.
    Wei, Han-Xun
    Zhang, Yongda
    Zhao, Wenyi
    Dufour, Marine
    Li, Guisheng
    Farina, Vittorio
    Senanayake, Chris H.
    JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (09): : 4558 - 4562
  • [43] Synthesis of 5-pyridyl-2-furaldehydes via palladium-catalyzed cross-coupling with triorganozincates
    Gauthier, DR
    Szumigala, RH
    Dormer, PG
    Armstrong, JD
    Volante, RP
    Reider, PJ
    ORGANIC LETTERS, 2002, 4 (03) : 375 - 378
  • [44] Palladium-catalyzed cross-coupling reaction of alkenyl aluminums with 2-bromobenzo[b]furans
    Wen, Chang
    Jiang, Xin
    Wu, Kun
    Luo, Ruiqiang
    Li, Qinghan
    RSC ADVANCES, 2020, 10 (33) : 19610 - 19614
  • [45] Synthesis of 4-alkynylpyrrolo[2,3-d]pyrimidines by palladium-catalyzed cross-coupling reactions
    Tumkevicius, Sigitas
    Masevicius, Viktoras
    SYNTHESIS-STUTTGART, 2007, 24 (24): : 3815 - 3820
  • [46] A novel route to 2,3-disubstituted indoles via palladium-catalyzed three-component coupling of aryl iodide, o-alkenylphenyl isocyanide and amine
    Onitsuka, K
    Suzuki, S
    Takahashi, S
    TETRAHEDRON LETTERS, 2002, 43 (35) : 6197 - 6199
  • [47] Stacking patterns of thieno[3,2-b]-thiophenes functionalized by sequential palladium-catalyzed Suzuki and Heck cross-coupling reactions
    Hien Nguyen
    Ngan Nguyen Bich
    Dang, Tung T.
    Van Meervelt, Luc
    ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 2014, 70 : 895 - +
  • [48] Facile synthesis of 2-alkyl substituted carbapenems via palladium-catalyzed cross-coupling reaction
    Narukawa, Y
    Nishi, K
    Onoue, H
    TETRAHEDRON LETTERS, 1996, 37 (15) : 2589 - 2592
  • [49] Palladium-Catalyzed Cross-Coupling Reactions of Carboranes with Alkenes via Selective B-H Bond Activation
    Chang, Jia-Rui
    Cao, Hou-Ji
    Ma, Yan-Na
    Chen, Xuenian
    ORGANIC LETTERS, 2025, 27 (08) : 1858 - 1863
  • [50] Palladium-catalyzed Cross-coupling of 2-Benzo[b]thiophene or 2-Benzo[b]furan Aluminum with Heteroaryl or Alkynyl Bromides for the Synthesis of 2-Hetroaryl or Alkynyl Benzo[b]thiophene or Benzo[b]furan Derivatives
    Liang, Meng
    Pu, Jiaxia
    Jia, Xiaoying
    Han, Lirong
    Li, Qinghan
    LETTERS IN ORGANIC CHEMISTRY, 2024, 21 (02) : 116 - 123
12345