11族金属化合物を触媒として用いる新しい有機合成反応  [in Japanese] New Synthetic Reactions Using Group 11 Metal Compounds as a Catalyst  [in Japanese]

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Abstract

This article presents several synthetic reactions by using a catalyst containing group 11 metals. We recently found an unprecedented reaction between an alkynylsilane and CuCl to produce the corresponding alkynylcopper (I) in DMI (1, 3-dimethy1-2-imidazolidinone). This transformation was applied to the synthesis of alkynyl ketones catalyzed by CuCl. A new and convenient procedure for the stereo- and chemoselective reduction of carbonyl compounds by use of a complex of copper (I) hydride generated from a hydrosilane and a copper (I) salt is described. A new method for the synthesis of enol esters (<I>O</I>-acylated products) from silyl enol ethers by use of a copper (I) salt is also described. An unprecedented cleavage reaction of the silicon-silicon bond in a disilane with a Cu (I) salt and its new 1, 4-addition reaction toward α, β-unsaturated carbonyl compounds in the presence of a catalytic amount of a Cu (I) salt is reported. Thus under these conditions, organosilyl-, hydrido-, alkynyl-, aryl- and heteroarylsilanes were smoothly converted to the corresponding organocopper reagents. Similarly, Au (I) complexes efficiently catalyze the dehydrogenative dimerization of trialkylstannanes and hydrosilylation of aldehydes. The present method provides new synthetic tools.

Journal

  • Journal of Synthetic Organic Chemistry, Japan

    Journal of Synthetic Organic Chemistry, Japan 58(4), 274-284, 2000-04-01

    The Society of Synthetic Organic Chemistry, Japan

References:  104

  • 1 / 2
  • <no title>

    MARCINIEC B.

    Comprehensive Handbook on Hydrosilylation, 1992

    Cited by (9)

  • <no title>

    ABEL E. W.

    Comprehensive Organometallic Chemistry II 10, 1995

    Cited by (2)

  • <no title>

    AGER D. J.

    J. Chem. Soc., Chem. Commun. 1978, 177

    Cited by (2)

  • <no title>

    AGER D. J.

    J. Chem. Soc., Perkin. Trans. 1, 2520

    Cited by (1)

  • <no title>

    LIPSHUTZ B. H.

    J.Org.Chem. 54, 4975, 1989

    Cited by (5)

  • <no title>

    LIPSHUTZ B. H.

    J. Am. Chem. Soc. 120, 4021, 1998

    Cited by (2)

  • <no title>

    FLEMING I.

    Organocopper Reagents A Practical Approach, 1994

    Cited by (1)

  • <no title>

    YOSHIDA J.

    Organometallics 1, 369, 1982

    Cited by (2)

  • <no title>

    玉尾皓平

    有合化 38, 769, 1980

    Cited by (1)

  • <no title>

    URATA H.

    Tetrahedron Lett. 32, 99, 1991

    Cited by (1)

  • <no title>

    TAKEDA T.

    Chem. Lett. 1999, 821

    Cited by (2)

  • <no title>

    FRANZ A. K.

    J. Am. Chem. Soc. 121, 949, 1999

    Cited by (1)

  • <no title>

    ITO H.

    Tetrahedron Lett. 38, 3977, 1997

    Cited by (4)

  • <no title>

    GREENE T. W.

    Protective Groups in Organic Synthesis, 1999

    Cited by (13)

  • <no title>

    MACOMBER D. W.

    J. Am. Chem. Soc. 105, 5325, 1983

    Cited by (1)

  • <no title>

    LERMONTOV S. A.

    Tetrahedron Lett. 37, 4051, 1996

    Cited by (3)

  • <no title>

    SAZONOVA V. A.

    Zh. Obshch. Khim. 26, 1876, 1956

    Cited by (1)

  • <no title>

    POSNER G. H.

    Organic Reactions 22, 380, 1975

    Cited by (1)

  • <no title>

    BIRKOFER L.

    Chem. Ber. 96, 3280, 1963

    Cited by (2)

  • <no title>

    UTIMOTO K.

    Tetrahedron Lett. 19, 2301, 1978

    Cited by (1)

  • <no title>

    SUGITA H.

    Chem. Lett. 1996, 379

    Cited by (1)

  • <no title>

    IKEGASHIRA K.

    Chem. Commun. 1997, 1039

    Cited by (6)

  • <no title>

    NISHIHARA Y.

    Chem. Lett. 1997, 1233

    Cited by (2)

  • <no title>

    NISHIHARA Y.

    Tetrahedron Lett. 39, 4075, 1998

    Cited by (3)

  • <no title>

    ITO H.

    Chem.Lett. 1997, 639

    Cited by (3)

  • <no title>

    YOSHIDA J.

    Organometallics 1, 542, 1982

    Cited by (6)

  • <no title>

    細見彰

    有合化 47, 831, 1989

    Cited by (3)

  • <no title>

    HOSOMI A.

    Rev. Heteroatom Chem. 7, 214, 1992

    Cited by (1)

  • <no title>

    HOSOMI A.

    Chem. Pharm. Bull. 36, 4622, 1988

    Cited by (2)

  • <no title>

    HOJO M.

    Bull. Soc. Chim. Fr. 132, 499, 1995

    Cited by (3)

  • <no title>

    HATANAKA Y.

    J. Org. Chem. 53, 918, 1988

    Cited by (6)

  • <no title>

    HIYAMA T.

    Pure Appl. Chem. 66, 1471, 1994

    Cited by (10)

  • <no title>

    MATSUHASHI H.

    Tetrahedron Lett. 36, 1539, 1995

    Cited by (3)

  • <no title>

    HIRABAYASHI K.

    Org. Lett. 1, 299, 1999

    Cited by (7)

  • <no title>

    ALLRED G. D.

    J. Am. Chem. Soc. 118, 2748, 1996

    Cited by (4)

  • <no title>

    ZHANG S.

    J.Org.Chem. 62, 2312, 1997

    Cited by (2)

  • <no title>

    FARINA V.

    Organic Reactions 50, 1997

    Cited by (2)

  • <no title>

    HAN X.

    J. Am. Chem. Soc. 121, 7600, 1999

    Cited by (3)

  • <no title>

    KANG S.-K.

    J.Org.Chem. 62, 4208, 1997

    Cited by (6)

  • <no title>

    KANG S. -K.

    J. Chem. Soc., Perkin Trans. 1, 797, 1997

    Cited by (1)

  • <no title>

    DONDONI A.

    Synthesis 1998

    Cited by (1)

  • <no title>

    MARCOUX J. F.

    J. Am. Chem. Soc. 119, 10539, 1997

    Cited by (1)

  • <no title>

    TAMAO K.

    Tetrahedron Lett. 30, 6051, 1989

    Cited by (4)

  • <no title>

    ITO H.

    Tetrahedron Lett. 38, 8887, 1997

    Cited by (2)

  • <no title>

    SAEGUSA T.

    J. Am. Chem. Soc. 89, 2240, 1967

    Cited by (1)

  • <no title>

    RYU I.

    Organometallics 8, 2279, 1989

    Cited by (1)

  • <no title>

    KUNAI A.

    Organometallics 11, 2708

    Cited by (1)

  • <no title>

    YOSHIDA J.

    Organometallics 14, 567, 1995

    Cited by (2)

  • <no title>

    KUNAI A.

    Organometallics 15, 2478, 1995

    Cited by (1)

  • <no title>

    KIRA M.

    Tetrahedron Lett. 30, 1099, 1989

    Cited by (5)

  • <no title>

    KOBAYASHI S.

    J. Am. Chem. Soc. 117, 6392, 1995

    Cited by (4)

  • <no title>

    LIU H. Q.

    Can. J. Chem. 70, 107, 1992

    Cited by (1)

  • <no title>

    SCHUBERT U.

    Chem. Ber. 127, 2189, 1994

    Cited by (1)

  • <no title>

    LORENZ C.

    Chem. Ber. 128, 1267, 1995

    Cited by (1)

  • <no title>

    SCHUBERT U.

    Inorg. Chem. 36, 1258, 1997

    Cited by (2)

  • <no title>

    SEMMELHACK M. F.

    J. Org. Chem. 42, 3180, 1977

    Cited by (1)

  • <no title>

    TSUDA T.

    J. Org. Chem. 52, 439, 1987

    Cited by (2)

  • <no title>

    MAHONEY W. S.

    J. Am. Chem. Soc. 110, 291, 1988

    Cited by (2)

  • <no title>

    LIPSHUTZ B. H.

    Synlett 1, 64, 1989

    Cited by (1)

  • <no title>

    LIPSHUTZ B. H.

    Organometallics in Synthesis A Manual 335, 1994

    Cited by (1)

  • <no title>

    伊藤肇

    日本化学会第74春季年会 309, 1998

    Cited by (1)

  • <no title>

    MORI A.

    Chem. Commun. 1997, 2159

    Cited by (2)

  • <no title>

    LIPSHUTZ B. H.

    Tetrahedron Lett. 39, 4627, 1998

    Cited by (1)

  • <no title>

    MORI A.

    Tetrahedron 55, 4573, 1999

    Cited by (2)

  • <no title>

    APPELLA D. H.

    J. Am. Chem. Soc. 121, 9473, 1999

    Cited by (2)

  • <no title>

    伊藤肇

    日本化学会第76春季年会, 1999

    Cited by (1)

  • <no title>

    SHIMADA H.

    Chem. Lett. 1995, 671

    Cited by (3)

  • <no title>

    COREY E. J.

    Tetrahedron Lett. 24, 2821, 1983

    Cited by (3)

  • <no title>

    HONDA T.

    Chem. Cornmun. 1997, 369

    Cited by (1)

  • <no title>

    HIRAO T.

    J. Org. Chem. 61, 366, 1996

    Cited by (5)

  • <no title>

    SVATOS A.

    Synlett 1998, 549

    Cited by (1)

  • <no title>

    HIRAO T.

    Synlett 1999, 175

    Cited by (4)

  • <no title>

    HUDLICKY M.

    Reductions in Organic Chemistry, 1996

    Cited by (3)

  • <no title>

    TROST B. M.

    "Comprehensive Organic Synthesis", 1991

    Cited by (5)

  • <no title>

    JOHNSON W. S.

    J. Am. Chem. Soc. 82, 3409, 1960

    Cited by (1)

  • <no title>

    KAINAN E.

    reference 523

    Cited by (1)

  • <no title>

    ITO H.

    J. Organomet. Chem. 574, 102, 1998

    Cited by (1)

  • <no title>

    ITO H.

    Tetrahedron Lett. 39, 6295, 1998

    Cited by (2)

  • <no title>

    ITO Y.

    J. Org. Chem. 45, 2022, 1980

    Cited by (1)

  • <no title>

    ITO Y.

    J. Am. Chem. Soc. 97, 649, 1975

    Cited by (5)

  • <no title>

    KOBAYASHI Y.

    Chem. Pharm. Bull. 28, 262, 1980

    Cited by (4)

  • <no title>

    RYU I.

    J. Am. Chem. Soc. 105, 7192, 1983

    Cited by (1)

  • <no title>

    PAGENKOPF B. L.

    Angew. Chem., Int. Ed. 37, 3124, 1998

    Cited by (3)

  • <no title>

    SHARMA H. K.

    Chem. Rev. 95, 1351, 1995

    Cited by (12)

  • <no title>

    HORN K. A.

    Chem. Rev. 95, 1317, 1995

    Cited by (10)

  • <no title>

    ITO Y.

    J. Org. Chem. 56, 1948, 1991

    Cited by (15)

  • <no title>

    YAMASHITA H.

    Chem. Lett. 1993, 315

    Cited by (3)

  • <no title>

    YAMASHITA H.

    Macromolecules 26, 2143, 1993

    Cited by (3)

  • <no title>

    ITO H.

    Tetrahedron Lett. 40, 7807, 1999

    Cited by (1)

  • <no title>

    GROHMANN A.

    Comprehensive Organometallic Chemistry II 3, 1-56, 1995

    Cited by (1)

  • <no title>

    小宮三四郎

    有合化 46, 1195, 1988

    Cited by (1)

  • <no title>

    KOMIYA S.

    J. Am. Chem. Soc. 98, 7255, 1976

    Cited by (1)

  • <no title>

    KOMIYA S.

    Organometallics 4, 684, 1985

    Cited by (3)

  • <no title>

    TELES J. H.

    Angew. Chem., Int. Ed. 37, 1415, 1998

    Cited by (1)

  • <no title>

    XU Q.

    J.Org.Chem. 62, 1594, 1997

    Cited by (5)

  • <no title>

    ITO Y.

    J. Am. Chem. Soc. 108, 6405, 1986

    Cited by (5)

  • <no title>

    KOMIYA S.

    Gold Bull. 29, 131, 1996

    Cited by (2)

  • <no title>

    FUKUDA Y.

    J. Org. Chem. 56, 3729, 1991

    Cited by (5)

  • <no title>

    DAVIES A. G.

    Organotin Chemistry 203 and 239, 1997

    Cited by (1)

  • <no title>

    伊藤肇

    第46回有機金属化学討論会 B 249, 1999

    Cited by (1)

  • 1 / 2

Codes

  • NII Article ID (NAID)
    10008819511
  • NII NACSIS-CAT ID (NCID)
    AN0024521X
  • Text Lang
    JPN
  • Article Type
    ART
  • ISSN
    00379980
  • NDL Article ID
    5341942
  • NDL Source Classification
    ZP11(科学技術--化学・化学工業--有機化学・有機化学工業)
  • NDL Call No.
    Z17-256
  • Data Source
    CJP  NDL  J-STAGE 
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