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Volumn , Issue 14, 2009, Pages 2354-2359

New and efficient iron halide mediated synthesis of alkenyl halides through coupling of alkynes and alcohols

Author keywords

Alcohols; Alkenyl halides; Alkynes; Iron; Sustainable chemistry

Indexed keywords


EID: 66149143042     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200900104     Document Type: Article
Times cited : (54)

References (79)
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    • d) recent review on Stille coupling reactions: P. Espinet, A. M. Echavarren, Angew. Chem. Int. Ed. 2004, 43, 4704-4734 and references cited therein;
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    • f) review on Suzuki coupling reactions: N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457-2483;
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    • and references cited therein
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    • For a few recent examples of the catalytic activation of alcohols, see: a
    • For a few recent examples of the catalytic activation of alcohols, see: a) H. Qin, N. Yamagiwa, S. Matsunga, M. Shibaski, Angew. Chem. Int. Ed. 2007, 46, 409-413;
    • (2007) Angew. Chem. Int. Ed , vol.46 , pp. 409-413
    • Qin, H.1    Yamagiwa, N.2    Matsunga, S.3    Shibaski, M.4
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    • 3-catalyzed activation of alcohols, see: a U. Jana, S. Maiti, S. Biswas, Tetrahedron Lett. 2008, 49, 858-862;
    • 3-catalyzed activation of alcohols, see: a) U. Jana, S. Maiti, S. Biswas, Tetrahedron Lett. 2008, 49, 858-862;
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    • 3 under heating at 50 °C. Surprisingly, under their reaction conditions the reactions of allylic alcohol and propargylic alcohol did not work, see: Z.-Q. Liu, J. Wang, J. Han, Y. Zhao, B. Zhou, Tetrahedron Lett. 2009, 50, 1240-1242;
    • 3 under heating at 50 °C. Surprisingly, under their reaction conditions the reactions of allylic alcohol and propargylic alcohol did not work, see: Z.-Q. Liu, J. Wang, J. Han, Y. Zhao, B. Zhou, Tetrahedron Lett. 2009, 50, 1240-1242;
  • 55
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    • the same author also reported the reaction of benzylic halides with alkynes in the presence of iron salts for the synthesis of alkenyl halides, see: Z.-Q. Liu, J. Wang, Y. Zhao, B. Zhou, Adv. Synth. Catal. 2009, 351, 371-374
    • the same author also reported the reaction of benzylic halides with alkynes in the presence of iron salts for the synthesis of alkenyl halides, see: Z.-Q. Liu, J. Wang, Y. Zhao, B. Zhou, Adv. Synth. Catal. 2009, 351, 371-374.
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    • and references cited therein. For the synthesis of 1,4-pentadienes, see
    • For the synthesis of 1,4-pentadienes, see: G. W. Kabalka, M. Al-Masaum, Org. Lett. 2006, 8, 11-13, and references cited therein.
    • (2006) Org. Lett , vol.8 , pp. 11-13
    • Kabalka, G.W.1    Al-Masaum, M.2
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    • [8];
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