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

被引:3
|
作者
Liang, Meng [1 ,2 ]
Pu, Jiaxia [1 ,2 ]
Jia, Xiaoying [1 ,2 ]
Han, Lirong [1 ,2 ]
Li, Qinghan [1 ,2 ,3 ]
机构
[1] Southwest Minzu Univ, Coll Chem & Environm, Chengdu 610041, Peoples R China
[2] Southwest Minzu Univ, Coll Chem & Environm, Key Lab Gen Chem Natl Ethn Affairs Commiss, Chengdu 610041, Peoples R China
[3] Southwest Minzu Univ, Coll Chem & Environm, POB 610041, Chengdu, Peoples R China
关键词
Palladium; 2-benzo[b]thiophene; 2-benzo[b]furan; alkynyl bromide; heteroaryl aluminum; cross-coupling reaction; ONE-POT SYNTHESIS; ELECTROPHILIC CYCLIZATION; RESEARCH PROGRESS; TERMINAL ALKYNES; FUNCTIONALIZATION; NANOPARTICLES; HYDROALKOXYLATION; BENZOTHIOPHENES; BENZOFURANS; ANNULATION;
D O I
10.2174/1570178620666230821142342
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An alternative method for the synthesis of 2-heteroaryl or alkynyl benzo[b]thiophene or furan derivatives via direct palladium-catalyzed cross-coupling of 2-benzo[b]thiophene or furan aluminum with heteroaryl or alkynyl bromides, respectively, has been successfully developed. This case is remarkable as the same catalytic system could simultaneously produce either 2-substituted benzo[b]thiophene or furan derivatives.
引用
收藏
页码:116 / 123
页数:8
相关论文
共 50 条
  • [1] PALLADIUM-CATALYZED ARYLATION OF FURAN, THIOPHENE, BENZO[B]FURAN AND BENZO[B]THIOPHENE
    OHTA, A
    AKITA, Y
    OHKUWA, T
    CHIBA, M
    FUKUNAGA, R
    MIYAFUJI, A
    NAKATA, T
    TANI, N
    AOYAGI, Y
    HETEROCYCLES, 1990, 31 (11) : 1951 - 1958
  • [2] Synthesis of the 2-alkynyl benzo[b]furanes/benzo[b]thiophenes from the cross-coupling reaction of benzo[b]furanyl/ benzo[b]thiophene aluminum reagents with gem-dibromoolefin derivatives catalyzed by palladium
    Pu, Jia-Xia
    Hou, Jin-Song
    Han, Li-Rong
    Jia, Xiao-Ying
    Li, Qing-Han
    TETRAHEDRON, 2024, 162
  • [3] Synthesis and characterization of benzo[c]thiophene analogs incorporating benzo[b]thiophene/1-hexylindole/benzo[b]furan
    Clement, J. Arul
    Gunasekaran, Pethaiah
    Mohanakrishnan, Arasambattu K.
    TETRAHEDRON, 2009, 65 (21) : 4113 - 4123
  • [4] STUDY ON FORMATION OF PENTAATOMIC LACTONES ON 2,3 POSITIONS OF BENZO(B)FURAN,BENZO(B) THIOPHENE AND BENZO(B)SELENOPHENE
    CHRISTIAENS, L
    RENSON, M
    BULLETIN DES SOCIETES CHIMIQUES BELGES, 1972, 81 (11-1): : 609 - 622
  • [5] H-1-NMR SPECTRA OF THE 2-TRIFLUOROACETYL DERIVATIVES OF BENZO[B]FURAN AND BENZO[B]THIOPHENE
    BENASSI, R
    FOLLI, U
    IAROSSI, D
    SCHENETTI, L
    TADDEI, F
    ORGANIC MAGNETIC RESONANCE, 1984, 22 (03): : 197 - 198
  • [6] PREPARATIVE SYNTHESIS OF BENZO[B]THIOPHENE, BENZO[B]SELENOPHENE AND BENZO[B]TELLUROPHENE DERIVATIVES
    LENDEL, VG
    PAKH, BJ
    PETRUS, VV
    KIJAK, MJ
    MIGALINA, JV
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1990, (10): : 1331 - 1334
  • [7] OXIDATION OF FURAN, PYRROLE, THIOPHENE, BENZO[B]FURAN, AND BENZO[B]THIOPHENE WITH OXODIPEROXOMOLYBDENUM (VI), MOO5.HMPA
    CHIEN, CS
    KAWASAKI, T
    SAKAMOTO, M
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1985, 33 (11) : 5071 - 5074
  • [8] New Synthesis of Benzo[b]furan-, Benzo[b]thiophene- and Benzo[b]selenophene-3-acetic Acids
    S. V. Tolkunov
    A. I. Khizhan
    Chemistry of Heterocyclic Compounds, 2003, 39 (4) : 539 - 540
  • [9] Palladium Catalyzed Suzuki Cross-Coupling of 3-Iodo-2-(methylthio)-benzo[b]furan Derivatives: Synthesis of 3-Aryl-2-(methylthio)benzo[b]furans
    Gay, Rafaela M.
    Manarin, Flavia
    Brandao, Ricardo
    Zeni, Gilson
    JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2010, 21 (09) : 1635 - 1641
  • [10] Synthesis of 2-Alkenyl- and 2-Alkynyl-benzo[b]phospholes by Using Palladium-Catalyzed Cross-Coupling Reactions
    Matano, Yoshihiro
    Hayashi, Yukiko
    Suda, Kayo
    Kimura, Yoshifumi
    Imahori, Hiroshi
    ORGANIC LETTERS, 2013, 15 (17) : 4458 - 4461