Facile One-Pot Coupling−Aminovinylation Approach to Push−Pull Chromophores: Alkyne Activation by Sonogashira Coupling
- 24 January 2003
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 68 (4) , 1503-1511
- https://doi.org/10.1021/jo026470o
Abstract
A straightforward coupling−aminovinylation sequence of terminal alkynes 1, electron-deficient heteroaryl halides 2, and secondary amines 4 furnishes highly solvochromic push−pull chromophores 5 in good yields. Semiempirical calculations (PM3) suggest that the aminovinylation proceeds in a stepwise fashion through a zwitterionic intermediate with a final rate-determining intramolecular protonation. Crucial parameters for the success of the amine addition are the relative LUMO energies and the charge distribution at the β-alkynyl carbon atom.Keywords
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