메뉴 건너뛰기




Volumn 119, Issue 29, 1997, Pages 6781-6786

Lewis acid catalyzed trans-allylsilylation of unactivated alkynes

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE DERIVATIVE; ALLYL COMPOUND; SILANE DERIVATIVE; TRIMETHYLSILYL DERIVATIVE;

EID: 0030859171     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja970443b     Document Type: Article
Times cited : (91)

References (49)
  • 2
    • 84989456545 scopus 로고
    • For reviews, see: (a) Normant, J. F.; Alexakis, A. Synthesis 1981, 841 (organo Li, Mg, Zn, B, Al, and Cu compounds). (b) Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1989, 28, 38 (stoichiometric organo Li, Mg, and Zn and catalytic Ni, Pd, Pt compounds). (c) Negishi, E. Pure Appl. Chem. 1981, 53, 2333 (organo Al/Ti and Al/Zr systems). (d) Knochel, P. Comprehensive Organometallic Chemistry II; Able, E. W., Stone, F. G. A., Wilkinson, G.; Eds.; Pergamon Press: Oxford, 1995; Vol. 11, p 159 (organo Li, Mg, Zn, B, Al, Cu, Hg/Pd, Ni, and Mn compounds). (e) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, p 865. (f) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207 (organo Li, Mg, Zn, B, and Al compounds).
    • (1981) Synthesis , pp. 841
    • Normant, J.F.1    Alexakis, A.2
  • 3
    • 84990107570 scopus 로고
    • For reviews, see: (a) Normant, J. F.; Alexakis, A. Synthesis 1981, 841 (organo Li, Mg, Zn, B, Al, and Cu compounds). (b) Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1989, 28, 38 (stoichiometric organo Li, Mg, and Zn and catalytic Ni, Pd, Pt compounds). (c) Negishi, E. Pure Appl. Chem. 1981, 53, 2333 (organo Al/Ti and Al/Zr systems). (d) Knochel, P. Comprehensive Organometallic Chemistry II; Able, E. W., Stone, F. G. A., Wilkinson, G.; Eds.; Pergamon Press: Oxford, 1995; Vol. 11, p 159 (organo Li, Mg, Zn, B, Al, Cu, Hg/Pd, Ni, and Mn compounds). (e) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, p 865. (f) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207 (organo Li, Mg, Zn, B, and Al compounds).
    • (1989) Angew. Chem., Int. Ed. Engl. , vol.28 , pp. 38
    • Oppolzer, W.1
  • 4
    • 84937194211 scopus 로고
    • For reviews, see: (a) Normant, J. F.; Alexakis, A. Synthesis 1981, 841 (organo Li, Mg, Zn, B, Al, and Cu compounds). (b) Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1989, 28, 38 (stoichiometric organo Li, Mg, and Zn and catalytic Ni, Pd, Pt compounds). (c) Negishi, E. Pure Appl. Chem. 1981, 53, 2333 (organo Al/Ti and Al/Zr systems). (d) Knochel, P. Comprehensive Organometallic Chemistry II; Able, E. W., Stone, F. G. A., Wilkinson, G.; Eds.; Pergamon Press: Oxford, 1995; Vol. 11, p 159 (organo Li, Mg, Zn, B, Al, Cu, Hg/Pd, Ni, and Mn compounds). (e) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, p 865. (f) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207 (organo Li, Mg, Zn, B, and Al compounds).
    • (1981) Pure Appl. Chem. , vol.53 , pp. 2333
    • Negishi, E.1
  • 5
    • 0001342014 scopus 로고
    • Able, E. W., Stone, F. G. A., Wilkinson, G.; Eds.; Pergamon Press: Oxford
    • For reviews, see: (a) Normant, J. F.; Alexakis, A. Synthesis 1981, 841 (organo Li, Mg, Zn, B, Al, and Cu compounds). (b) Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1989, 28, 38 (stoichiometric organo Li, Mg, and Zn and catalytic Ni, Pd, Pt compounds). (c) Negishi, E. Pure Appl. Chem. 1981, 53, 2333 (organo Al/Ti and Al/Zr systems). (d) Knochel, P. Comprehensive Organometallic Chemistry II; Able, E. W., Stone, F. G. A., Wilkinson, G.; Eds.; Pergamon Press: Oxford, 1995; Vol. 11, p 159 (organo Li, Mg, Zn, B, Al, Cu, Hg/Pd, Ni, and Mn compounds). (e) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, p 865. (f) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207 (organo Li, Mg, Zn, B, and Al compounds).
    • (1995) Comprehensive Organometallic Chemistry II , vol.11 , pp. 159
    • Knochel, P.1
  • 6
    • 0001522634 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford
    • For reviews, see: (a) Normant, J. F.; Alexakis, A. Synthesis 1981, 841 (organo Li, Mg, Zn, B, Al, and Cu compounds). (b) Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1989, 28, 38 (stoichiometric organo Li, Mg, and Zn and catalytic Ni, Pd, Pt compounds). (c) Negishi, E. Pure Appl. Chem. 1981, 53, 2333 (organo Al/Ti and Al/Zr systems). (d) Knochel, P. Comprehensive Organometallic Chemistry II; Able, E. W., Stone, F. G. A., Wilkinson, G.; Eds.; Pergamon Press: Oxford, 1995; Vol. 11, p 159 (organo Li, Mg, Zn, B, Al, Cu, Hg/Pd, Ni, and Mn compounds). (e) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, p 865. (f) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207 (organo Li, Mg, Zn, B, and Al compounds).
    • (1991) Comprehensive Organic Synthesis , vol.4 , pp. 865
    • Knochel, P.1
  • 7
    • 4243893500 scopus 로고
    • For reviews, see: (a) Normant, J. F.; Alexakis, A. Synthesis 1981, 841 (organo Li, Mg, Zn, B, Al, and Cu compounds). (b) Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1989, 28, 38 (stoichiometric organo Li, Mg, and Zn and catalytic Ni, Pd, Pt compounds). (c) Negishi, E. Pure Appl. Chem. 1981, 53, 2333 (organo Al/Ti and Al/Zr systems). (d) Knochel, P. Comprehensive Organometallic Chemistry II; Able, E. W., Stone, F. G. A., Wilkinson, G.; Eds.; Pergamon Press: Oxford, 1995; Vol. 11, p 159 (organo Li, Mg, Zn, B, Al, Cu, Hg/Pd, Ni, and Mn compounds). (e) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, p 865. (f) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207 (organo Li, Mg, Zn, B, and Al compounds).
    • (1993) Chem. Rev. , vol.93 , pp. 2207
    • Yamamoto, Y.1    Asao, N.2
  • 18
    • 1842413380 scopus 로고    scopus 로고
    • note
    • Jung and co-workers reported cis-allylsilylation of phenylacetylene (ref 4h). However, their stereochemical assignment of reaction product was not correct (see ref 5, note 7).
  • 19
    • 1842411033 scopus 로고    scopus 로고
    • note
    • Negishi reported cis-allylalumination of unactivated acetylenes in the presence of Zr catalyst (ref 4e). The present addition proceeds in a trans manner. Accordingly, it seems that the allylalumimum species is not involved as a reactive intermediate.
  • 20
    • 1842293042 scopus 로고    scopus 로고
    • note
    • 3 did not catalyze the addition reaction of allyltrimethylsilane to 1d.
  • 21
    • 1842334203 scopus 로고    scopus 로고
    • note
    • 4 also catalyzed these reactions; however, the yields of 3 in these cases were usually slightly lower.
  • 24
    • 0001391988 scopus 로고
    • Barton, D. H. R., Ollis, W. d., Eds.; Pergamon Press: Oxford
    • (c) Fleming, I. In Comprehensive Organic Chemistry; Barton, D. H. R., Ollis, W. d., Eds.; Pergamon Press: Oxford, 1979; Vol. III, p 541.
    • (1979) Comprehensive Organic Chemistry , vol.3 , pp. 541
    • Fleming, I.1
  • 35
    • 0004531220 scopus 로고
    • Patai, S., Rappoport, Z., Eds.; John Wiley & Sons: Chichester
    • (f) Apeloig, Y. In The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.; John Wiley & Sons: Chichester, 1989; Part 1, p 196.
    • (1989) The Chemistry of Organic Silicon Compounds , Issue.1 PART , pp. 196
    • Apeloig, Y.1
  • 42
    • 1842328297 scopus 로고
    • Although the so-called "half-reaction time" data are very approximate, they are only useful for the rough estimation of relative reactivities. For example, see: Fleming, I.; Langley, J. A. J. Chem. Soc., Perkin Trans. 1 1981, 1412.
    • (1981) J. Chem. Soc., Perkin Trans. 1 , pp. 1412
    • Fleming, I.1    Langley, J.A.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.