Palladium(0)-catalyzed cyclization of electron-deficient enynes and enediynes

The Journal of Organic Chemistry
Yoshihiko YamamotoKenji Itoh

Abstract

In the presence of a Pd(0) precatalyst, Pd2(bq)2(nbe)2 or Pd2(dba)3, 1,6-enyne esters were heated in refluxing benzene to give cyclodimers as single regioisomers. On the other hand, the combination of the Pd(0) precatalyst and triphenyl phosphite gave rise to various cycloisomerization products depending on the substitution pattern of the enyne esters. Six-membered ring cycloisomerization products were predominantly obtained from enyne esters bearing methallyl or 2-phenyl-2-propenyl moieties, while other enyne esters afforded normal five-membered ring cycloisomerization products. Intramolecular [2 + 2 + 2] cyclocotrimerization of enediyne esters also proceeded in the presence of the Pd(0) precatalyst and triphenylphosphine to give fused cyclohexadienes.

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Citations

Feb 15, 2017·Journal of the American Chemical Society·David A PetroneMark Lautens
Feb 27, 2016·Chemistry : a European Journal·Gema Domínguez, Javier Pérez-Castells
Oct 27, 2011·Chemistry : a European Journal·Mana IshidaKen Tanaka
Dec 17, 2010·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Anna Pla-Quintana, Anna Roglans
Apr 3, 2008·Angewandte Chemie·Véronique MicheletJean-Pierre Genêt
May 28, 2010·Chemical Society Reviews·Phillip A Inglesby, P Andrew Evans
Dec 17, 2005·Chemistry : a European Journal·Cristina Nieto-OberhuberAntonio M Echavarren
Jun 27, 2014·Chemistry : a European Journal·Hye Mi OhYoung Keun Chung
Sep 4, 2008·Chemistry : a European Journal·Silvia García-RubínCarlos Saá
Feb 17, 2018·Chemical Communications : Chem Comm·Qian ZhangTeck-Peng Loh
Nov 21, 2007·Journal of the American Chemical Society·Sha LouScott E Schaus
May 28, 2009·The Journal of Organic Chemistry·Yu LanYun-Dong Wu
Apr 21, 2020·Journal of the American Chemical Society·Chengpeng WangGuangbin Dong

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