Synthesis of multisubstituted 1,3-butadienes using the ruthenium-catalysed double addition of trimethylsilyldiazomethane to alkynylboronates

Organic and Biomolecular Chemistry

Volumn 3, Issue 7, 2005, Pages 1263-1268

  Morita, Ryotaro ^a   Shirakawa, Eiji ^b   Tsnchimoto, Teruhisa ^a   Kawakami, Yusuke ^a  

^a JAPAN ADVANCED INSTITUTE OF SCIENCE AND TECHNOLOGY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID; ADDITION REACTIONS; CATALYSIS; ESTERS; EVAPORATION; GEL PERMEATION CHROMATOGRAPHY; HYDROLYSIS; REACTION KINETICS; RUTHENIUM; SOLVENTS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

1,3-BUTADIENES; MUKAIYAMA ALDOL REACTION; SUZUKI-MIYAURA COUPLING REACTION; TETRAFLUOROACETIC ACID;

BUTADIENE;

BETULACEAE; LATEOLABRAX JAPONICUS;

EID: 17444375708     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b501990g     Document Type: Article

References (27)

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3. The cross-coupling reaction of alkenylmetals with alkenyl halides, i.e., the Suzuki-Miyaura and the Kosugi-Migita-Stille coupling reactions, should be one of the most effective methods leading to conjugated dienes in a stereospecific way. However, the coupling reaction sometimes can be cumbersome since both substrates, multisubstituled alkenylmetals and alkenyl halides, must be prepared stereoselectively prior to the coupling. For the Suzuki-Miyaura coupling reaction, see: (a) N. Miyaura, H. Suginome and A. Suzuki, Tetrahedron Lett., 1981, 22, 127-130; (b) N. Miyaura and A. Suzuki, Chem. Rev., 1995, 95, 2457-2483; (c) N. Miyaura, Top. Curr. Chem., 2002, 219, 11-59; (d) For the Kosugi-Migita-Stille coupling reaction, see: M. Kosugi, K. Sasazawa, Y. Shimizu and T. Migita, Chem. Lett., 1977, 301-302; (e) V. Farina, V. Krishnamurthy and W. J. Scott, Org. React., 1997, 50, 1-652. 4 Although the Mizoroki-Heck reaction may be an alternative for the cross-coupling reaction, low reactivity of multisubstituted alkenes upon the reaction with alkenyl halides may be a major drawback. For recent reviews of the Mizoroki-Heck reaction, see: S. Bröse and A. de Meijere, in Metal-catalyzed Cross-coupling Reactions, ed. F. Diederich and P. J. Stang, Wiley-VCH, Weinheim, 1998, ch. 3, pp. 99-166; G. T. Crisp, Chem. Soc. Rev., 1998, 27, 427-436; I. P. Beletskaya and A. V. Cheprakov, Chem. Rev., 2000, 100, 3009-3066.
4. The cross-coupling reaction of alkenylmetals with alkenyl halides, i.e., the Suzuki-Miyaura and the Kosugi-Migita-Stille coupling reactions, should be one of the most effective methods leading to conjugated dienes in a stereospecific way. However, the coupling reaction sometimes can be cumbersome since both substrates, multisubstituled alkenylmetals and alkenyl halides, must be prepared stereoselectively prior to the coupling. For the Suzuki-Miyaura coupling reaction, see: (a) N. Miyaura, H. Suginome and A. Suzuki, Tetrahedron Lett., 1981, 22, 127-130; (b) N. Miyaura and A. Suzuki, Chem. Rev., 1995, 95, 2457-2483; (c) N. Miyaura, Top. Curr. Chem., 2002, 219, 11-59; (d) For the Kosugi-Migita-Stille coupling reaction, see: M. Kosugi, K. Sasazawa, Y. Shimizu and T. Migita, Chem. Lett., 1977, 301-302; (e) V. Farina, V. Krishnamurthy and W. J. Scott, Org. React., 1997, 50, 1-652. 4 Although the Mizoroki-Heck reaction may be an alternative for the cross-coupling reaction, low reactivity of multisubstituted alkenes upon the reaction with alkenyl halides may be a major drawback. For recent reviews of the Mizoroki-Heck reaction, see: S. Bröse and A. de Meijere, in Metal-catalyzed Cross-coupling Reactions, ed. F. Diederich and P. J. Stang, Wiley-VCH, Weinheim, 1998, ch. 3, pp. 99-166; G. T. Crisp, Chem. Soc. Rev., 1998, 27, 427-436; I. P. Beletskaya and A. V. Cheprakov, Chem. Rev., 2000, 100, 3009-3066.
5. The cross-coupling reaction of alkenylmetals with alkenyl halides, i.e., the Suzuki-Miyaura and the Kosugi-Migita-Stille coupling reactions, should be one of the most effective methods leading to conjugated dienes in a stereospecific way. However, the coupling reaction sometimes can be cumbersome since both substrates, multisubstituled alkenylmetals and alkenyl halides, must be prepared stereoselectively prior to the coupling. For the Suzuki-Miyaura coupling reaction, see: (a) N. Miyaura, H. Suginome and A. Suzuki, Tetrahedron Lett., 1981, 22, 127-130; (b) N. Miyaura and A. Suzuki, Chem. Rev., 1995, 95, 2457-2483; (c) N. Miyaura, Top. Curr. Chem., 2002, 219, 11-59; (d) For the Kosugi-Migita-Stille coupling reaction, see: M. Kosugi, K. Sasazawa, Y. Shimizu and T. Migita, Chem. Lett., 1977, 301-302; (e) V. Farina, V. Krishnamurthy and W. J. Scott, Org. React., 1997, 50, 1-652. 4 Although the Mizoroki-Heck reaction may be an alternative for the cross-coupling reaction, low reactivity of multisubstituted alkenes upon the reaction with alkenyl halides may be a major drawback. For recent reviews of the Mizoroki-Heck reaction, see: S. Bröse and A. de Meijere, in Metal-catalyzed Cross-coupling Reactions, ed. F. Diederich and P. J. Stang, Wiley-VCH, Weinheim, 1998, ch. 3, pp. 99-166; G. T. Crisp, Chem. Soc. Rev., 1998, 27, 427-436; I. P. Beletskaya and A. V. Cheprakov, Chem. Rev., 2000, 100, 3009-3066.
6. The cross-coupling reaction of alkenylmetals with alkenyl halides, i.e., the Suzuki-Miyaura and the Kosugi-Migita-Stille coupling reactions, should be one of the most effective methods leading to conjugated dienes in a stereospecific way. However, the coupling reaction sometimes can be cumbersome since both substrates, multisubstituled alkenylmetals and alkenyl halides, must be prepared stereoselectively prior to the coupling. For the Suzuki-Miyaura coupling reaction, see: (a) N. Miyaura, H. Suginome and A. Suzuki, Tetrahedron Lett., 1981, 22, 127-130; (b) N. Miyaura and A. Suzuki, Chem. Rev., 1995, 95, 2457-2483; (c) N. Miyaura, Top. Curr. Chem., 2002, 219, 11-59; (d) For the Kosugi-Migita-Stille coupling reaction, see: M. Kosugi, K. Sasazawa, Y. Shimizu and T. Migita, Chem. Lett., 1977, 301-302; (e) V. Farina, V. Krishnamurthy and W. J. Scott, Org. React., 1997, 50, 1-652. 4 Although the Mizoroki-Heck reaction may be an alternative for the cross-coupling reaction, low reactivity of multisubstituted alkenes upon the reaction with alkenyl halides may be a major drawback. For recent reviews of the Mizoroki-Heck reaction, see: S. Bröse and A. de Meijere, in Metal-catalyzed Cross-coupling Reactions, ed. F. Diederich and P. J. Stang, Wiley-VCH, Weinheim, 1998, ch. 3, pp. 99-166; G. T. Crisp, Chem. Soc. Rev., 1998, 27, 427-436; I. P. Beletskaya and A. V. Cheprakov, Chem. Rev., 2000, 100, 3009-3066.
7. The cross-coupling reaction of alkenylmetals with alkenyl halides, i.e., the Suzuki-Miyaura and the Kosugi-Migita-Stille coupling reactions, should be one of the most effective methods leading to conjugated dienes in a stereospecific way. However, the coupling reaction sometimes can be cumbersome since both substrates, multisubstituled alkenylmetals and alkenyl halides, must be prepared stereoselectively prior to the coupling. For the Suzuki-Miyaura coupling reaction, see: (a) N. Miyaura, H. Suginome and A. Suzuki, Tetrahedron Lett., 1981, 22, 127-130; (b) N. Miyaura and A. Suzuki, Chem. Rev., 1995, 95, 2457-2483; (c) N. Miyaura, Top. Curr. Chem., 2002, 219, 11-59; (d) For the Kosugi-Migita-Stille coupling reaction, see: M. Kosugi, K. Sasazawa, Y. Shimizu and T. Migita, Chem. Lett., 1977, 301-302; (e) V. Farina, V. Krishnamurthy and W. J. Scott, Org. React., 1997, 50, 1-652. 4 Although the Mizoroki-Heck reaction may be an alternative for the cross-coupling reaction, low reactivity of multisubstituted alkenes upon the reaction with alkenyl halides may be a major drawback. For recent reviews of the Mizoroki-Heck reaction, see: S. Bröse and A. de Meijere, in Metal-catalyzed Cross-coupling Reactions, ed. F. Diederich and P. J. Stang, Wiley-VCH, Weinheim, 1998, ch. 3, pp. 99-166; G. T. Crisp, Chem. Soc. Rev., 1998, 27, 427-436; I. P. Beletskaya and A. V. Cheprakov, Chem. Rev., 2000, 100, 3009-3066.
8. The cross-coupling reaction of alkenylmetals with alkenyl halides, i.e., the Suzuki-Miyaura and the Kosugi-Migita-Stille coupling reactions, should be one of the most effective methods leading to conjugated dienes in a stereospecific way. However, the coupling reaction sometimes can be cumbersome since both substrates, multisubstituled alkenylmetals and alkenyl halides, must be prepared stereoselectively prior to the coupling. For the Suzuki-Miyaura coupling reaction, see: (a) N. Miyaura, H. Suginome and A. Suzuki, Tetrahedron Lett., 1981, 22, 127-130; (b) N. Miyaura and A. Suzuki, Chem. Rev., 1995, 95, 2457-2483; (c) N. Miyaura, Top. Curr. Chem., 2002, 219, 11-59; (d) For the Kosugi-Migita-Stille coupling reaction, see: M. Kosugi, K. Sasazawa, Y. Shimizu and T. Migita, Chem. Lett., 1977, 301-302; (e) V. Farina, V. Krishnamurthy and W. J. Scott, Org. React., 1997, 50, 1-652. 4 Although the Mizoroki-Heck reaction may be an alternative for the cross-coupling reaction, low reactivity of multisubstituted alkenes upon the reaction with alkenyl halides may be a major drawback. For recent reviews of the Mizoroki-Heck reaction, see: S. Bröse and A. de Meijere, in Metal-catalyzed Cross-coupling Reactions, ed. F. Diederich and P. J. Stang, Wiley-VCH, Weinheim, 1998, ch. 3, pp. 99-166; G. T. Crisp, Chem. Soc. Rev., 1998, 27, 427-436; I. P. Beletskaya and A. V. Cheprakov, Chem. Rev., 2000, 100, 3009-3066.
9. The cross-coupling reaction of alkenylmetals with alkenyl halides, i.e., the Suzuki-Miyaura and the Kosugi-Migita-Stille coupling reactions, should be one of the most effective methods leading to conjugated dienes in a stereospecific way. However, the coupling reaction sometimes can be cumbersome since both substrates, multisubstituled alkenylmetals and alkenyl halides, must be prepared stereoselectively prior to the coupling. For the Suzuki-Miyaura coupling reaction, see: (a) N. Miyaura, H. Suginome and A. Suzuki, Tetrahedron Lett., 1981, 22, 127-130; (b) N. Miyaura and A. Suzuki, Chem. Rev., 1995, 95, 2457-2483; (c) N. Miyaura, Top. Curr. Chem., 2002, 219, 11-59; (d) For the Kosugi-Migita-Stille coupling reaction, see: M. Kosugi, K. Sasazawa, Y. Shimizu and T. Migita, Chem. Lett., 1977, 301-302; (e) V. Farina, V. Krishnamurthy and W. J. Scott, Org. React., 1997, 50, 1-652. 4 Although the Mizoroki-Heck reaction may be an alternative for the cross-coupling reaction, low reactivity of multisubstituted alkenes upon the reaction with alkenyl halides may be a major drawback. For recent reviews of the Mizoroki-Heck reaction, see: S. Bröse and A. de Meijere, in Metal-catalyzed Cross-coupling Reactions, ed. F. Diederich and P. J. Stang, Wiley-VCH, Weinheim, 1998, ch. 3, pp. 99-166; G. T. Crisp, Chem. Soc. Rev., 1998, 27, 427-436; I. P. Beletskaya and A. V. Cheprakov, Chem. Rev., 2000, 100, 3009-3066.
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