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Volumn 58, Issue 52, 2002, Pages 10429-10435

Copper(I)-catalyzed reaction of acylzirconocene chloride: Cross-coupling and conjugate addition

Author keywords

Acylzirconocene chloride; Allenyl ketone; Propargylic halides

Indexed keywords

ACYLZIRCONOCENE CHLORIDE; ALLYL COMPOUND; ANION; COPPER COMPLEX; HALIDE; KETONE; UNCLASSIFIED DRUG; ZIRCONOCENE;

EID: 0037164612     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)01422-9     Document Type: Article
Times cited : (19)

References (41)
  • 12
    • 0001209154 scopus 로고
    • It has been reported that the reactivity of alky- or alkenylziconocene chloride derived from the hydrozirconation of alkene or alkyne by Schwartz reagent would be altered by the preparative method of the employed Schwartz reagent. That is, contamination of the Schwartz reagent would have a serious effect on the subsequent reactivity of the derived zirconocene complexes. See Ref. 17a. To avoid the uncertainty, the Schwartz reagent prepared by the Buchwald's procedure was employed throughout the present reactions. (a) Buchwald S.L., LaMaire S.J., Nielsen R.B., Watson B.T., King S.M. Tetrahedron Lett. 28:1987;3895 (b) Buchwald S.L., LaMaire S.J., Nielsen R.B., Watson B.T., King S.M. Org. Synth. 71:1993;77.
    • (1987) Tetrahedron Lett. , vol.28 , pp. 3895
    • Buchwald, S.L.1    LaMaire, S.J.2    Nielsen, R.B.3    Watson, B.T.4    King, S.M.5
  • 13
    • 0001918119 scopus 로고
    • It has been reported that the reactivity of alky- or alkenylziconocene chloride derived from the hydrozirconation of alkene or alkyne by Schwartz reagent would be altered by the preparative method of the employed Schwartz reagent. That is, contamination of the Schwartz reagent would have a serious effect on the subsequent reactivity of the derived zirconocene complexes. See Ref. 17a. To avoid the uncertainty, the Schwartz reagent prepared by the Buchwald's procedure was employed throughout the present reactions. (a) Buchwald S.L., LaMaire S.J., Nielsen R.B., Watson B.T., King S.M. Tetrahedron Lett. 28:1987;3895 (b) Buchwald S.L., LaMaire S.J., Nielsen R.B., Watson B.T., King S.M. Org. Synth. 71:1993;77.
    • (1993) Org. Synth. , vol.71 , pp. 77
    • Buchwald, S.L.1    LaMaire, S.J.2    Nielsen, R.B.3    Watson, B.T.4    King, S.M.5
  • 14
    • 0001209154 scopus 로고
    • It has been reported that the reactivity of alky- or alkenylziconocene chloride derived from the hydrozirconation of alkene or alkyne by Schwartz reagent would be altered by the preparative method of the employed Schwartz reagent. That is, contamination of the Schwartz reagent would have a serious effect on the subsequent reactivity of the derived zirconocene complexes. See Ref. 17a. To avoid the uncertainty, the Schwartz reagent prepared by the Buchwald's procedure was employed throughout the present reactions. (a) Buchwald S.L., LaMaire S.J., Nielsen R.B., Watson B.T., King S.M. Tetrahedron Lett. 28:1987;3895 (b) Buchwald S.L., LaMaire S.J., Nielsen R.B., Watson B.T., King S.M. Org. Synth. 71:1993;77.
    • (1987) Tetrahedron Lett. , vol.28 , pp. 3895
    • Buchwald, S.L.1    LaMaire, S.J.2    Nielsen, R.B.3    Watson, B.T.4    King, S.M.5
  • 15
    • 0001918119 scopus 로고
    • It has been reported that the reactivity of alky- or alkenylziconocene chloride derived from the hydrozirconation of alkene or alkyne by Schwartz reagent would be altered by the preparative method of the employed Schwartz reagent. That is, contamination of the Schwartz reagent would have a serious effect on the subsequent reactivity of the derived zirconocene complexes. See Ref. 17a. To avoid the uncertainty, the Schwartz reagent prepared by the Buchwald's procedure was employed throughout the present reactions. (a) Buchwald S.L., LaMaire S.J., Nielsen R.B., Watson B.T., King S.M. Tetrahedron Lett. 28:1987;3895 (b) Buchwald S.L., LaMaire S.J., Nielsen R.B., Watson B.T., King S.M. Org. Synth. 71:1993;77.
    • (1993) Org. Synth. , vol.71 , pp. 77
    • Buchwald, S.L.1    LaMaire, S.J.2    Nielsen, R.B.3    Watson, B.T.4    King, S.M.5
  • 16
    • 0011957994 scopus 로고    scopus 로고
    • For a preliminary report on some aspects of the present study, see Ref. 3f
    • For a preliminary report on some aspects of the present study, see Ref. 3f.
  • 23
    • 0000379498 scopus 로고    scopus 로고
    • 2-C zirconacycles with propargyl halides has been demonstrated. (a)
    • 2-C zirconacycles with propargyl halides has been demonstrated. (a) Takahashi T., Tsai F.-Y., Li Y., Wang H., Kondo Y., yamanaka M., Nakajima K., Kotora M. J. Am. Chem. Soc. 124:2002;5059 (b) Kotora M., Noguchi Y., Takahashi T. Collect. Czech. Chem. Commun. 64:1999;1119.
    • (1999) Collect. Czech. Chem. Commun. , vol.64 , pp. 1119
    • Kotora, M.1    Noguchi, Y.2    Takahashi, T.3
  • 25
    • 0011958723 scopus 로고    scopus 로고
    • note
    • One of the reviewers pointed out the mechanistic aspects for the present Cu(I)-catalyzed coupling reactions with allylic halides: (1) an intervention of the oxyCu carbene as an actual reactive species, and (2) stereochemical aspects of the products. The reviewer suggested the possibility for the formation of cyclopropyl alkoxide by the addition of the oxyCu carbene species to the double bond of allylic halides and subsequent elimination of the halogen giving products 2. We assume that the present cross-coupling reactions would proceed through the nucleophilic attack of acyl-Cu 9 to the allylic halide, because of the recovery of starting materials in the reactions of homoallylic halide derivatives. However, we must await further studies to describe a detailed mechanism for the reaction. We appreciate the reviewer for generous suggestions, and the reaction mechanism will be reported in due course.
  • 26
    • 0003417469 scopus 로고
    • B.M. Trost, & I. Fleming. Oxford: Pergamon. p 169 and the references cited therein
    • Kozlowski J.A. Trost B.M., Fleming I. Comprehensive Organic Synthesis. 1991;Pergamon, Oxford. p 169 and the references cited therein.
    • (1991) Comprehensive Organic Synthesis
    • Kozlowski, J.A.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.