Reactions of Electron-Deficient Alkynes and Allenes under Phosphine Catalysis
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- 12 May 2001
- journal article
- research article
- Published by American Chemical Society (ACS) in Accounts of Chemical Research
- Vol. 34 (7) , 535-544
- https://doi.org/10.1021/ar000253x
Abstract
The development of some new synthetic reactions derived from nucleophilic addition of phosphines to electron-deficient carbon−carbon triple bonds is described. These reactions show that the phosphine plays the role of a nucleophile as well as an excellent leaving group. The central problem is to generate a 1,3-dipole from alkynoates or allenoates (2,3-butadienoates) by interaction with various phosphines. This study illuminates the unusual phenomena and shows how this understanding allows control of the reaction.Keywords
This publication has 6 references indexed in Scilit:
- One-pot, four-component synthesis of dialkyl [indane-1,3-dione-2-ylidene]alkoxysuccinatesTetrahedron Letters, 2000
- Carboxylates as pronucleophiles in the phosphine-catalyzed γ-addition reactionTetrahedron Letters, 1999
- Vinyltriphenylphosphonium salt mediated one-pot synthesis of functionalized 3-(triphenylphosphoranylidene)butyrolactonesTetrahedron Letters, 1997
- Facile Synthetic Method for the Preparation of Dithioacetals by the Double Conjugate Addition of Acetylenes Bearing Electron-Withdrawing Groups with ThiolsSynthetic Communications, 1996
- Total synthesis of hemibrevetoxin BJournal of the American Chemical Society, 1992
- Trihydrogen complexes of iridiumJournal of the American Chemical Society, 1988