Copper-Catalyzed Cross-Coupling Reactions of Bromoalkynols with Terminal Alkynes in Supercritical Carbon Dioxide

Huan-Feng Jiang; A.-Zhong Wang

doi:10.1055/s-2007-966058

PAPER

Copper-Catalyzed Cross-Coupling Reactions of Bromoalkynols with Terminal Alkynes in Supercritical Carbon Dioxide

Huan-Feng Jiang*, A-Zhong Wang
College of Chemistry, South China University of Technology, Guangzhou 510640, P. R. of China
Fax: +86(20)87112906; e-Mail: jianghf@scut.edu.cn;

Abstract

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Abstract

Copper-catalyzed cross-coupling reactions of bromoalkynols and terminal alkynes were carried out in supercritical carbon dioxide (scCO₂) to afford the corresponding unsymmetrical diynes with good yields. The reaction is sensitive to temperature and the pressure of CO₂. Methanol, as a cosolvent of scCO₂, could promote dissolution of the inorganic salt and thus facilitated the reaction. This new heterocoupling reaction system is more environmentally friendly than more traditional methods, since it uses scCO₂ as solvent and sodium acetate as base instead of amines.

Key words

unsymmetrical diynes - heterocoupling reaction - alkynes - supercritical carbon dioxide

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References

<A NAME="RF05107SS-1A">1a</A> Sabitha G. Reddy CS. Yadav JS. Tetrahedron Lett. 2006, 47: 4513

<A NAME="RF05107SS-1B">1b</A> Gung BW. Fox RM. Falconer R. Shissler D. Tetrahedron: Asymmetry 2006, 17: 40

<A NAME="RF05107SS-1C">1c</A> Yun H. Chou T.-C. Dong H. Tian Y. Li Y.-M. Danishefsky SJ. J. Org. Chem. 2005, 70: 10375

<A NAME="RF05107SS-1D">1d</A> Alves D. Nogueira CW. Zeni G. Tetrahedron Lett. 2005, 46: 8761

<A NAME="RF05107SS-1E">1e</A> Lu W. Zheng G. Aisa HA. Cai J. Tetrahedron Lett. 1998, 39: 9521

<A NAME="RF05107SS-1F">1f</A> Quayle P. Rahman S. Herbert J. Tetrahedron Lett. 1995, 36: 8087

<A NAME="RF05107SS-1G">1g</A> Wityak J. Chan JB. Synth. Commun. 1991, 21: 977

<A NAME="RF05107SS-1H">1h</A> Hopf H. Krause N. Tetrahedron Lett. 1985, 26: 3323

<A NAME="RF05107SS-2A">2a</A> Nie X. Wang G. J. Org. Chem. 2006, 71: 4734

<A NAME="RF05107SS-2B">2b</A> Klinger C. Vostrowsky O. Hirsch A. Eur. J. Org. Chem. 2006, 6: 1508

<A NAME="RF05107SS-2C">2c</A> Hayashi N. Matsukihira T. Miyabayashi K. Miyake M. Higuchi H. Tetrahedron Lett. 2006, 47: 5585

<A NAME="RF05107SS-2D">2d</A> Vail SA. Krawczuk PJ. Guldi DM. Palkar A. Echegoyen L. Tome JPC. Fazio MA. Schuster DI. Chem. Eur. J. 2005, 11: 3375

<A NAME="RF05107SS-2E">2e</A> Holmes BT. Pennington WT. Hanks TW. Synth. Commun. 2003, 33: 2447

<A NAME="RF05107SS-2F">2f</A> Siemen P. Livingston RC. Diederich F. Angew. Chem. Int. Ed. 2000, 39: 2632

<A NAME="RF05107SS-3A">3a</A> Cadiot P. Chodkiewicz W. In Chemistry of Acetylenes Viehe HG. Dekker; New York: 1969. Chap. 9. p.597-647

<A NAME="RF05107SS-3B">3b</A> Chodkiewicz W. Ann. Chim. (Paris) 1957, 2: 819

<A NAME="RF05107SS-4">4</A> Marino JP. Nguyen HN. J. Org. Chem. 2002, 67: 6841

<A NAME="RF05107SS-5">5</A> Alami M. Ferri F. Tetrahedron Lett. 1996, 37: 2763

<A NAME="RF05107SS-6">6</A> Montierth JM. DeMario DR. Kurth MJ. Schore NE. Tetrahedron 1998, 54: 11741

<A NAME="RF05107SS-7">7</A> Nishihara Y. Ikegashira K. Mori A. Hiyama T. Tetrahedron Lett. 1998, 39: 4075

<A NAME="RF05107SS-8">8</A> Amatore C. Blart E. Genet JP. J. Org. Chem. 1995, 60: 6829

<A NAME="RF05107SS-9">9</A> Wityak J. Chan JB. Synth. Commun. 1991, 21: 977

For reviews on using scCO₂ as reaction medium, see:

<A NAME="RF05107SS-10A">10a</A> Clarke D. Ali MA. Clifford AA. Parratt A. Rose P. Schwinn D. Bannwarth W. Rayner CM. Curr. Top. Med. Chem. 2004, 4: 729

<A NAME="RF05107SS-10B">10b</A> Leitner W. Acc. Chem. Res. 2002, 35: 746

<A NAME="RF05107SS-10C">10c</A> Darr JA. Poliakoff M. Chem. Rev. 1999, 99: 495

<A NAME="RF05107SS-10D">10d</A> Jessop PG. Chem. Rev. 1999, 99: 475

<A NAME="RF05107SS-11A">11a</A> Li J.-H. Jiang H.-F. Chem. Commun. 1999, 2369

<A NAME="RF05107SS-11B">11b</A> Jiang H.-F. Tang J.-Y. Wang A.-Z. Deng G.-H. Yang S.-R. Synthesis 2006, 1155

<A NAME="RF05107SS-12A">12a</A> Wang Z.-Y. Jiang H.-F. Qi C.-R. Wang Y.-G. Dong Y.-S. Liu H.-L. Green Chem. 2005, 7: 582

<A NAME="RF05107SS-12B">12b</A> Cheng J.-S. Jiang H.-F. Eur. J. Org. Chem. 2004, 643

<A NAME="RF05107SS-13">13</A> Tortosa-Estorach C. Ruiz N. Masdeu-Bulto AM. Chem. Commun. 2006, 2789

<A NAME="RF05107SS-14">14</A> Jacobson GB. Lee CT. Johnston KP. Tumas W. J. Am. Chem. Soc. 1999, 121: 11902

<A NAME="RF05107SS-15">15</A> Nye SA. Potts KT. Synthesis 1988, 375

<A NAME="RF05107SS-16">16</A> Dabdoub MJ. Baroni ACM. Lenardao EJ. Gianeti TR. Hurtado GR. Tetrahedron 2001, 57: 4271