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Green Chemistry
Volumn 12, Issue 9, 2010, Pages 1576-1579
Solvent-free solid acid-catalyzed nucleophilic substitution of propargylic alcohols: A green approach for the synthesis of 1,4-diynes
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EID: 77956385130     PISSN: 14639262     EISSN: 14639270     Source Type: Journal    
DOI: 10.1039/c0gc00117a     Document Type: Article
Times cited : (26)
References (57)
  • 20
    • 84905497776 scopus 로고    scopus 로고
    • US 2009/0312274 A1
    • I. Cohen, US Pat., US 2009/0312274 A1, 2009.
    • (2009) US Pat.
    • Cohen, I.1
  • 46
    • 73149089890 scopus 로고    scopus 로고
    • Solvent-free reactions have attracted tremendous attention. For selected examples, see
    • Solvent-free reactions have attracted tremendous attention. For selected examples, see: P. D. Macleod Z. Li C.-J. Li Tetrahedron 2010 66 1045-1050.
    • (2010) Tetrahedron , vol.66 , pp. 1045-1050
    • Macleod, P.D.1    Li, Z.2    Li, C.-J.3
  • 54
    • 85032768019 scopus 로고    scopus 로고
    • As discussed above, K10 mont treated with 1 M HCl at 80 °C is the most appropriate catalyst for this reaction. From here onwards, “H-K10 mont” refers to K10 montmorillonite treated with 1 M HCl at 80 °C
    • As discussed above, K10 mont treated with 1 M HCl at 80 °C is the most appropriate catalyst for this reaction. From here onwards, “H-K10 mont” refers to K10 montmorillonite treated with 1 M HCl at 80 °C.
  • 55
    • 0002534158 scopus 로고    scopus 로고
    • This idea was proposed by one of the referees and we consider it an effective supplement to our work. We are grateful to the referee. For the Sheldon test, see
    • This idea was proposed by one of the referees and we consider it an effective supplement to our work. We are grateful to the referee. For the Sheldon test, see: H. E. B. Lempers R. A. Sheldon J. Catal. 1998 175 62-69.
    • (1998) J. Catal. , vol.175 , pp. 62-69
    • Lempers, H.E.B.1    Sheldon, R.A.2
  • 56
    • 0000511757 scopus 로고
    • Inspired by one of the referees, we examined the substitution of propargylic alcohol with some other alkynyl nucleophiles, including terminal alkynes and terminal TMS-substituted aliphatic alkynes. Unfortunately, our attempt to insert these nucleophiles into propargylic alcohol failed (see the ESI, Table S1). However, the unsatisfactory results provided indirect proof for the proposed mechanism: aryl and TMS groups in the nucleophiles seem essential for the reaction due to their well-known ability to stabilize this alkenyl cationic intermediate. Several α-phenyl-β-silyl-substituted vinyl cations have been characterized, see
    • Inspired by one of the referees, we examined the substitution of propargylic alcohol with some other alkynyl nucleophiles, including terminal alkynes and terminal TMS-substituted aliphatic alkynes. Unfortunately, our attempt to insert these nucleophiles into propargylic alcohol failed (see the ESI, Table S1). However, the unsatisfactory results provided indirect proof for the proposed mechanism: aryl and TMS groups in the nucleophiles seem essential for the reaction due to their well-known ability to stabilize this alkenyl cationic intermediate. Several α-phenyl-β-silyl-substituted vinyl cations have been characterized, see: H.-U. Siehl F.-P. Kaufmann J. Am. Chem. Soc. 1992 114 4937-4939.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 4937-4939
    • Siehl, H.-U.1    Kaufmann, F.-P.2

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.