메뉴 건너뛰기




Volumn 58, Issue 41, 2002, Pages 8227-8235

Remarkable enhancement of Lewis acidity of chlorosilane by the combined use of indium(III) chloride

Author keywords

Allylation; Catalysts; Indium and compounds; Silicon and compounds; Silicon halides

Indexed keywords

INDIUM CHLORIDE; LEWIS ACID; SILANE DERIVATIVE; SILICON;

EID: 0037037851     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)00972-9     Document Type: Article
Times cited : (62)

References (64)
  • 4
    • 0003417469 scopus 로고
    • B.M. Trost, & I. Fleming. Oxford: Pergamon
    • (d) Heathcock C.H. Trost B.M., Fleming I., Comprehensive Organic Synthesis. 1991;Pergamon, Oxford. Part 2.(e) Paquette L.A. Trost B.M., Fleming I., Comprehensive Organic Synthesis. 1991;Pergamon, Oxford. Part 5 and references are cited therein.
    • (1991) Comprehensive Organic Synthesis
    • Heathcock, C.H.1
  • 5
    • 0003417469 scopus 로고
    • B.M. Trost, & I. Fleming. Oxford: Pergamon and references are cited therein
    • (a) Ishihara K. Yamamoto H., Lewis Acids in Organic Synthesis. Vol. 1:2000;Wiley-VCH, Weinheim. Part 4. (b) Ooi T., Maruoka K. Yamamoto H., Lewis Acids in Organic Synthesis. Vol. 1:2000;Wiley-VCH, Weinheim. © Scheiber S.L. Trost B.M., Fleming I., Comprehensive Organic Synthesis. 1991;Pergamon, Oxford. Part 1. (d) Heathcock C.H. Trost B.M., Fleming I., Comprehensive Organic Synthesis. 1991;Pergamon, Oxford. Part 2. (e) Paquette L.A. Trost B.M., Fleming I., Comprehensive Organic Synthesis. 1991;Pergamon, Oxford. Part 5 and references are cited therein.
    • (1991) Comprehensive Organic Synthesis
    • Paquette, L.A.1
  • 15
    • 0037156378 scopus 로고    scopus 로고
    • For the recent reports on using indium compounds as a catalyst. See: (a) Muthusamy S., Babu S.A., Gunanathan C. Tetrahedron Lett. 43:2002;3133-3136 (b) Yadav J.S., Subba Reddy B.V., Sadashiv K., Harikishan K. Tetrahedron Lett. 43:2002;2099-2101 © Yadav J.S., Reddy B.V.S., Raman J.V., Niranjan N., Kiran Kumar S., Kunwar A.C. Tetrahedron Lett. 43:2002;2095-2098 (d) Viswanathan G.S., Li C.J. Tetrahedron Lett. 43:2002;1613-1615 (e) Choudhary V.R., Jana S.K., Patil N.S. Tetrahedron Lett. 43:2002;1105-1107 (f) Kelly B.G., Gilheany D.G. Tetrahedron Lett. 43:2002;887-890 (g) Inoue K., Sawada A., Shibata I., Baba A. J. Am. Chem. Soc. 124:2002;960-961 (h) Friestad G.K., Ding H. Angew. Chem. Int. Ed. 40:2001;4491-4493.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 3133-3136
    • Muthusamy, S.1    Babu, S.A.2    Gunanathan, C.3
  • 16
    • 0037060973 scopus 로고    scopus 로고
    • For the recent reports on using indium compounds as a catalyst. See: (a) Muthusamy S., Babu S.A., Gunanathan C. Tetrahedron Lett. 43:2002;3133-3136 (b) Yadav J.S., Subba Reddy B.V., Sadashiv K., Harikishan K. Tetrahedron Lett. 43:2002;2099-2101 © Yadav J.S., Reddy B.V.S., Raman J.V., Niranjan N., Kiran Kumar S., Kunwar A.C. Tetrahedron Lett. 43:2002;2095-2098 (d) Viswanathan G.S., Li C.J. Tetrahedron Lett. 43:2002;1613-1615 (e) Choudhary V.R., Jana S.K., Patil N.S. Tetrahedron Lett. 43:2002;1105-1107 (f) Kelly B.G., Gilheany D.G. Tetrahedron Lett. 43:2002;887-890 (g) Inoue K., Sawada A., Shibata I., Baba A. J. Am. Chem. Soc. 124:2002;960-961 (h) Friestad G.K., Ding H. Angew. Chem. Int. Ed. 40:2001;4491-4493.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 2099-2101
    • Yadav, J.S.1    Subba Reddy, B.V.2    Sadashiv, K.3    Harikishan, K.4
  • 17
    • 0037060940 scopus 로고    scopus 로고
    • For the recent reports on using indium compounds as a catalyst. See: (a) Muthusamy S., Babu S.A., Gunanathan C. Tetrahedron Lett. 43:2002;3133-3136 (b) Yadav J.S., Subba Reddy B.V., Sadashiv K., Harikishan K. Tetrahedron Lett. 43:2002;2099-2101 © Yadav J.S., Reddy B.V.S., Raman J.V., Niranjan N., Kiran Kumar S., Kunwar A.C. Tetrahedron Lett. 43:2002;2095-2098 (d) Viswanathan G.S., Li C.J. Tetrahedron Lett. 43:2002;1613-1615 (e) Choudhary V.R., Jana S.K., Patil N.S. Tetrahedron Lett. 43:2002;1105-1107 (f) Kelly B.G., Gilheany D.G. Tetrahedron Lett. 43:2002;887-890 (g) Inoue K., Sawada A., Shibata I., Baba A. J. Am. Chem. Soc. 124:2002;960-961 (h) Friestad G.K., Ding H. Angew. Chem. Int. Ed. 40:2001;4491-4493.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 2095-2098
    • Yadav, J.S.1    Reddy, B.V.S.2    Raman, J.V.3    Niranjan, N.4    Kiran Kumar, S.5    Kunwar, A.C.6
  • 18
    • 0037170103 scopus 로고    scopus 로고
    • For the recent reports on using indium compounds as a catalyst. See: (a) Muthusamy S., Babu S.A., Gunanathan C. Tetrahedron Lett. 43:2002;3133-3136 (b) Yadav J.S., Subba Reddy B.V., Sadashiv K., Harikishan K. Tetrahedron Lett. 43:2002;2099-2101 © Yadav J.S., Reddy B.V.S., Raman J.V., Niranjan N., Kiran Kumar S., Kunwar A.C. Tetrahedron Lett. 43:2002;2095-2098 (d) Viswanathan G.S., Li C.J. Tetrahedron Lett. 43:2002;1613-1615 (e) Choudhary V.R., Jana S.K., Patil N.S. Tetrahedron Lett. 43:2002;1105-1107 (f) Kelly B.G., Gilheany D.G. Tetrahedron Lett. 43:2002;887-890 (g) Inoue K., Sawada A., Shibata I., Baba A. J. Am. Chem. Soc. 124:2002;960-961 (h) Friestad G.K., Ding H. Angew. Chem. Int. Ed. 40:2001;4491-4493.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 1613-1615
    • Viswanathan, G.S.1    Li, C.J.2
  • 19
    • 0037017030 scopus 로고    scopus 로고
    • For the recent reports on using indium compounds as a catalyst. See: (a) Muthusamy S., Babu S.A., Gunanathan C. Tetrahedron Lett. 43:2002;3133-3136 (b) Yadav J.S., Subba Reddy B.V., Sadashiv K., Harikishan K. Tetrahedron Lett. 43:2002;2099-2101 © Yadav J.S., Reddy B.V.S., Raman J.V., Niranjan N., Kiran Kumar S., Kunwar A.C. Tetrahedron Lett. 43:2002;2095-2098 (d) Viswanathan G.S., Li C.J. Tetrahedron Lett. 43:2002;1613-1615 (e) Choudhary V.R., Jana S.K., Patil N.S. Tetrahedron Lett. 43:2002;1105-1107 (f) Kelly B.G., Gilheany D.G. Tetrahedron Lett. 43:2002;887-890 (g) Inoue K., Sawada A., Shibata I., Baba A. J. Am. Chem. Soc. 124:2002;960-961 (h) Friestad G.K., Ding H. Angew. Chem. Int. Ed. 40:2001;4491-4493.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 1105-1107
    • Choudhary, V.R.1    Jana, S.K.2    Patil, N.S.3
  • 20
    • 0037185606 scopus 로고    scopus 로고
    • For the recent reports on using indium compounds as a catalyst. See: (a) Muthusamy S., Babu S.A., Gunanathan C. Tetrahedron Lett. 43:2002;3133-3136 (b) Yadav J.S., Subba Reddy B.V., Sadashiv K., Harikishan K. Tetrahedron Lett. 43:2002;2099-2101 © Yadav J.S., Reddy B.V.S., Raman J.V., Niranjan N., Kiran Kumar S., Kunwar A.C. Tetrahedron Lett. 43:2002;2095-2098 (d) Viswanathan G.S., Li C.J. Tetrahedron Lett. 43:2002;1613-1615 (e) Choudhary V.R., Jana S.K., Patil N.S. Tetrahedron Lett. 43:2002;1105-1107 (f) Kelly B.G., Gilheany D.G. Tetrahedron Lett. 43:2002;887-890 (g) Inoue K., Sawada A., Shibata I., Baba A. J. Am. Chem. Soc. 124:2002;960-961 (h) Friestad G.K., Ding H. Angew. Chem. Int. Ed. 40:2001;4491-4493.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 887-890
    • Kelly, B.G.1    Gilheany, D.G.2
  • 21
    • 0037065678 scopus 로고    scopus 로고
    • For the recent reports on using indium compounds as a catalyst. See: (a) Muthusamy S., Babu S.A., Gunanathan C. Tetrahedron Lett. 43:2002;3133-3136 (b) Yadav J.S., Subba Reddy B.V., Sadashiv K., Harikishan K. Tetrahedron Lett. 43:2002;2099-2101 © Yadav J.S., Reddy B.V.S., Raman J.V., Niranjan N., Kiran Kumar S., Kunwar A.C. Tetrahedron Lett. 43:2002;2095-2098 (d) Viswanathan G.S., Li C.J. Tetrahedron Lett. 43:2002;1613-1615 (e) Choudhary V.R., Jana S.K., Patil N.S. Tetrahedron Lett. 43:2002;1105-1107 (f) Kelly B.G., Gilheany D.G. Tetrahedron Lett. 43:2002;887-890 (g) Inoue K., Sawada A., Shibata I., Baba A. J. Am. Chem. Soc. 124:2002;960-961 (h) Friestad G.K., Ding H. Angew. Chem. Int. Ed. 40:2001;4491-4493.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 960-961
    • Inoue, K.1    Sawada, A.2    Shibata, I.3    Baba, A.4
  • 22
    • 0035803698 scopus 로고    scopus 로고
    • For the recent reports on using indium compounds as a catalyst. See: (a) Muthusamy S., Babu S.A., Gunanathan C. Tetrahedron Lett. 43:2002;3133-3136 (b) Yadav J.S., Subba Reddy B.V., Sadashiv K., Harikishan K. Tetrahedron Lett. 43:2002;2099-2101 © Yadav J.S., Reddy B.V.S., Raman J.V., Niranjan N., Kiran Kumar S., Kunwar A.C. Tetrahedron Lett. 43:2002;2095-2098 (d) Viswanathan G.S., Li C.J. Tetrahedron Lett. 43:2002;1613-1615 (e) Choudhary V.R., Jana S.K., Patil N.S. Tetrahedron Lett. 43:2002;1105-1107 (f) Kelly B.G., Gilheany D.G. Tetrahedron Lett. 43:2002;887-890 (g) Inoue K., Sawada A., Shibata I., Baba A. J. Am. Chem. Soc. 124:2002;960-961 (h) Friestad G.K., Ding H. Angew. Chem. Int. Ed. 40:2001;4491-4493.
    • (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 4491-4493
    • Friestad, G.K.1    Ding, H.2
  • 45
    • 84992275497 scopus 로고    scopus 로고
    • 3 solvent
    • 3 solvent.
  • 46
    • 84992275508 scopus 로고    scopus 로고
    • The smaller amounts of the combined catalyst were effective for the allylation (see ref. 14. Decompositon of allyltrimethylsilane and numerous side reactions (cf. Prins-type cyclization) tend to occur under large amounts of the combined catalyst
    • The smaller amounts of the combined catalyst were effective for the allylation (see Ref. 14). Decompositon of allyltrimethylsilane and numerous side reactions (cf. Prins-type cyclization) tend to occur under large amounts of the combined catalyst.
  • 47
    • 84992288067 scopus 로고    scopus 로고
    • 29Si NMR
    • 29Si NMR.
  • 48
    • 84992258449 scopus 로고    scopus 로고
    • 3SiCl. See Ref. 7b
    • 3SiCl. See Ref. 7b.
  • 49
    • 84992258453 scopus 로고    scopus 로고
    • There are a few reports of catalytic allylation of imines using allyltrimethylsilane. See Ref. 6h
    • There are a few reports of catalytic allylation of imines using allyltrimethylsilane. See Ref. 6h.
  • 50
    • 84992285919 scopus 로고    scopus 로고
    • Rearrangement plausibly proceeded via epoxide 17 shown in Scheme 4
    • Rearrangement plausibly proceeded via epoxide 17 shown in Scheme 4.
  • 51
    • 0032514970 scopus 로고    scopus 로고
    • 3-promoted rearrangement of epoxides to aldehydes was reported in; Ranu B.C., Jana U. J. Org. Chem. 63:1998;8212-8216.
    • (1998) J. Org. Chem. , vol.63 , pp. 8212-8216
    • Ranu, B.C.1    Jana, U.2
  • 52
    • 84992285910 scopus 로고    scopus 로고
    • In the case of the allylation of α-hydroxyketones, TBAF is not a suitable quenching reagent. The fluoride anion derived from TBAF was probably coordinated not to the silicon atom on the silylether, because a considerable amount of the silicon reagent or residue was found in the solution
    • In the case of the allylation of α-hydroxyketones, TBAF is not a suitable quenching reagent. The fluoride anion derived from TBAF was probably coordinated not to the silicon atom on the silylether, because a considerable amount of the silicon reagent or residue was found in the solution.
  • 53
    • 84992247907 scopus 로고    scopus 로고
    • We presume that 11a is the intermediate in the allylation of 5. The silylether formation from alcohols and allylsilanes under similar conditions has been reported in Ref. 13
    • We presume that 11a is the intermediate in the allylation of 5. The silylether formation from alcohols and allylsilanes under similar conditions has been reported in Ref. 13.
  • 54
    • 84992271149 scopus 로고    scopus 로고
    • 3 group is used for stabilization through the pπ-dπ interaction
    • 3 group is used for stabilization through the pπ-dπ interaction.
  • 55
    • 84992258460 scopus 로고    scopus 로고
    • Diallylation products were obtained when para-methoxybenzaldehyde was used. See Refs. 13e and 14. In this case, the stabilized carbocation formed after the first allylation tends to be further allylated
    • Diallylation products were obtained when para-methoxybenzaldehyde was used. See Refs. 13e and 14. In this case, the stabilized carbocation formed after the first allylation tends to be further allylated.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.