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Volumn 13, Issue 19, 2011, Pages 5100-5103

A practical, one-pot synthesis of highly substituted thiophenes and benzo[b]thiophenes from bromoenynes and o-alkynylbromobenzenes

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; ALKYNE; BENZOTHIOPHENE; BROMOBENZENE; THIOPHENE DERIVATIVE;

EID: 80054738957     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol201970m     Document Type: Article
Times cited : (99)

References (48)
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    • Cupric halide promoted: (e) Lu, W.-D.; Wu, M.-J. Tetrahedron 2007, 63, 356-362.
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    • Lu, W.-D.1    Wu, M.-J.2
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    • During the preparation of this manuscript a related paper has appeared that reports the use of thiourea as a dihydrosulfide surrogate in the synthesis of thioethers and benzo[b]thiophenes
    • During the preparation of this manuscript a related paper has appeared that reports the use of thiourea as a dihydrosulfide surrogate in the synthesis of thioethers and benzo[b]thiophenes. See: Kuhn, M.; Falk, F. C.; Paradies, J. Org. Lett. 2011, 13, 4100-4103.
    • (2011) Org. Lett. , vol.13 , pp. 4100-4103
    • Kuhn, M.1    Falk, F.C.2    Paradies, J.3
  • 32
  • 36
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    • For reports about the use of different mercapto surrogates in Pdcatalyzed C-S couplings
    • For reports about the use of different mercapto surrogates in Pdcatalyzed C-S couplings, see: (a) Itoh, M.; Mase, T. J. Org. Chem. 2006, 71, 2203-2206.
    • (2006) J. Org. Chem. , vol.71 , pp. 2203-2206
    • Itoh, M.1    Mase, T.2
  • 38
    • 15044353663 scopus 로고    scopus 로고
    • For the use of HSTIPS in Pd-catalyzed C-S couplings
    • For the use of HSTIPS in Pd-catalyzed C-S couplings, see: (a) Kreis, M.; Bráse, S. Adv. Synth. Catal. 2005, 47, 313-319.
    • (2005) Adv. Synth. Catal. , vol.47 , pp. 313-319
    • Kreis, M.1    Bráse, S.2
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    • 3 and different phosphine ligands such as Josiphos CyPFtBu (see ref 18b), XPhos, SPhos, DavePhos, and dppf for this coupling was comparable in terms of reaction rates and turnover numbers to the catalyst generated from Xantphos ligand. However, we selected Xantphos as a ligand due to its better availability
    • 3 and different phosphine ligands such as Josiphos CyPFtBu (see ref 18b), XPhos, SPhos, DavePhos, and dppf for this coupling was comparable in terms of reaction rates and turnover numbers to the catalyst generated from Xantphos ligand. However, we selected Xantphos as a ligand due to its better availability.
  • 41
    • 33947606582 scopus 로고    scopus 로고
    • For the use of KSAc in Pd-catalyzed C-S couplings
    • For the use of KSAc in Pd-catalyzed C-S couplings, see: (a) Lai, C.; Backes, B. J. Tetrahedron Lett. 2007, 48, 3033-3037.
    • (2007) J. Tetrahedron Lett. , vol.48 , pp. 3033-3037
    • Lai, C.1    Backes, B.2
  • 46
    • 84856547682 scopus 로고    scopus 로고
    • 2O (2/1) mixture as eluent and subsequent evaporation of the solvents afforded arylthiosilanes 4, which were not further purified
    • 2O (2/1) mixture as eluent and subsequent evaporation of the solvents afforded arylthiosilanes 4, which were not further purified.
  • 47
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    • The corresponding 3-unsubstitued derivatives 3 were also formed in small variable amounts. Nevertheless, they could be separated from the 3-functionalized benzo[b]thiophenes 7 by column chromatography
    • The corresponding 3-unsubstitued derivatives 3 were also formed in small variable amounts. Nevertheless, they could be separated from the 3-functionalized benzo[b]thiophenes 7 by column chromatography.
  • 48
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    • The use ofCsFfor the cleavage of the S-Si bond is not necessary in this case. A direct iodine-promoted cyclization provided similar results.
    • The use ofCsFfor the cleavage of the S-Si bond is not necessary in this case. A direct iodine-promoted cyclization provided similar results.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.