Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 37, 2007 - Issue 5
174
Views
7
CrossRef citations to date
0
Altmetric
Original Articles

Microwave‐Promoted, Solvent‐Free, Three‐Component Coupling of Aldehyde, Alkyne, and Amine Catalyzed by AgNO3

, , &
Pages 849-858 | Published online: 10 Mar 2007

References

  • Armstrong , R. W. , Combs , A. P. , Tempest , P. A. , Brown , S. D. and Keating , T. A. 1996 . Multiple‐component condensation strategies for combinatorial library synthesis . Acc. Chem. Res. , 29 : 123 – 131 .
  • Weber , L. , Illgen , K. and Almstetter , M. 1999 . Discovery of new multi component reactions with combinatorial methods . Synlett , : 366 – 374 .
  • Christian , F. and Erick , M. C. 2001 . Direct addition of TMS‐acetylene to aldimines catalyzed by a simple, commercially available Ir(I) complex . Org. Lett. , 3 : 4319 – 4321 .
  • Christopher , K. , Kurt , P. and Paul , K. 2002 . Enantioselective synthesis of propargylamines by copper‐catalyzed addition of alkynes to enamines . Angew. Chem. Int. Ed. , 41 : 2535 – 2538 .
  • Brasseur , D. , Marek , I. and Normant , J. F. 1996 . Diastereoselective synthesis of heterosubstituted organogembismetallic reagents: Application to a new propargylmetalation reaction of vinyl metals . Tetrahedron , 52 : 7235 – 7250 .
  • Aubrecht , K. B. , Winemiller , M. D. and Collum , D. B. 2000 . BF3‐mediated addition of lithium phenylacetylide to an imine: Correlations of structures, reactivities: BF3 · R3N derivatives as substitutes for BF3 · Et2O . J. Am. Chem. Soc. , 122 : 11084 – 11089 .
  • Akullian , L. C. , Snapper , M. L. and Hoveyda , A. H. 2003 . Three‐component enantioselective synthesis of propargylamines through Zr‐catalyzed additions of alkyl zinc reagents to alkynylimines . Angew. Chem. Int. Ed. , 42 : 4244 – 4247 .
  • Jiang , B. and Si , Y. G. 2004 . Highly enantioselective construction of a chiral tertiary carbon center by alkynylation of a cyclic N‐acyl ketimine: An efficient preparation of HIV therapeutics . Angew. Chem. Int. Ed. , 43 : 216 – 218 .
  • Mark , A. H. , Nobuyoshi , Y. , Ann , E. D. and Edward , J. J. G. 1995 . Lithium alkoxides of cinchona alkaloids as chiral controllers for enantioselective acetylide addition to cyclic N‐acyl ketimines . J. Org. Chem. , 60 : 1590 – 1594 .
  • Masataka , K. , Hiroaki , O. , Takashi , T. , Toshikazu , O. , Gregory , D. V. and Jon , C. 1990 . Crystal and molecular structure of dynemicin A: A novel 1,5‐diyn‐3‐ene antitumor antibiotic . J. Am. Chem. Soc. , 112 : 3715 – 3716 .
  • Li , C. J. and Wei , C. 2002 . Highly efficient grignard‐type imine additions via C‐H activation in water and under solvent‐free conditions . Chem. Commun. , : 268 – 270 .
  • Wei , C. and Li , C. J. 2002 . Enantioselective direct‐addition of terminal alkynes to imines catalyzed by copper(I) pybox complex in water and in toluene . J. Am. Chem. Soc. , 124 : 5638 – 5639 .
  • Shi , L. , Tu , Y.‐Q. , Wang , M. , Zhang , F.‐M. and Fan , C.‐A. 2004 . Microwave‐promoted three‐component coupling of aldehyde, alkyne, and amine via C‐H activation catalyzed by copper in water . Org. Lett. , 6 : 1001 – 1003 .
  • Ju , Y. , Li , C. J. and Rajender , S. V. 2004 . Microwave‐assisted Cu(I) catalyzed solvent‐free three component coupling of aldehyde, alkyne, and amine . QSAR Comb. Sci. , 23 : 891 – 894 .
  • Sreedhar , B. , Reddy , P. S. , Prakash , B. V. and Ravindra , A. 2005 . Ultrasound‐assisted rapid and efficient synthesis of propargylamines . Tetrahedron Lett. , 46 : 7019 – 7022 .
  • Wei , C. and Li , C. J. 2003 . A highly efficient three‐component coupling of aldehyde, alkyne, and amines via C‐H activation catalyzed by gold in water . J. Am. Chem. Soc. , 125 : 9584 – 9585 .
  • Wei , C. , Li , Z. and Li , C. J. 2003 . The first silver‐catalyzed three‐component coupling of aldehyde, alkyne, and amine . Org. Lett. , 5 : 4473 – 4475 .
  • Li , Z. , Wei , C. , Chen , L. , Rajender , S. V. and Li , C. J. 2004 . Three‐component coupling of aldehyde, alkyne, and amine catalyzed by silver in ionic liquid . Tetrahedron Lett. , 45 : 2443 – 2446 .
  • Kad , G. L. , Kaur , I. , Bhandari , M. and Singh , J. 2003 . Functional group transformations of diols, cyclic ethers, and lactones using aqueous hydrobromic acid and phase transfer catalyst under microwave irradiation . Org. Process Res. Dev. , 7 : 339 – 340 .
  • Garbacia , S. , Desai , B. , Lavastre , O. and Kappe , C. O. 2003 . Microwave‐assisted ring‐closing metathesis revisited: On the question of the nonthermal microwave effect . J. Org. Chem. , 68 : 9136 – 9139 .
  • Xu , G. and Wang , Y. G. 2004 . Microwave‐assisted amination from aryl triflates without base catalyst . Org. Lett. , 6 : 985 – 987 .
  • Hayes , B. L. 2002 . Microwave Synthesis, Chemistry at the Speed of Light Matthews, N. C. : CEM Publishing . Chapter 1, p. 16
  • Larhed , M. , Moberg , C. and Hallberg , A. 2002 . Microwave‐accelerated homogeneous catalysis in organic chemistry . Acc. Chem. Res. , 35 : 717 – 727 .
  • Villemin , D. and Caillot , F. 2001 . Microwave mediated palladium‐catalysed reactions on potassium fluoride/alumina without use of solvent . Tetrahedron Lett. , 42 : 639 – 642 .
  • Anastas , P. T. and Warner , J. C. 1998 . Green Chemistry: Theory and Practice Oxford : Oxford University Press .
  • Darr , J. A. and Poliakoff , M. 1999 . New directions in inorganic and metal‐organic coordination chemistry in supercritical fluids . Chem. Rev. , 99 : 495 – 542 .
  • Shezad , N. , Clifford , A. A. and Rayner , C. M. 2001 . Suppression of double bond isomerisation in intramolecular Heck reactions using supercritical carbon dioxide . Tetrahedron Lett. , 42 : 323 – 325 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.