63019-13-6Relevant articles and documents
Synthesis of tetrasubstituted olefins by Pd-catalyzed addition of arylboronic acids to internal alkynes
Zhou, Chengxiang,Larock, Richard C.
, p. 259 - 262 (2005)
(Chemical Equation Presented) Tetrasubstituted olefins are readily prepared by the Pd-catalyzed cis addition of two aryl groups from an arylboronic acid to opposite ends of the triple bond of internal alkynes. The synthesis proceeds under very mild reaction conditions and tolerates a wide variety of functional groups, including alcohol, aldehyde, ester, TMS, and acetal groups.
Asymmetric Hydrogenation of Unfunctionalized Tetrasubstituted Acyclic Olefins
Bachmann, Stephan,Bigler, Raphael,Denmark, Scott E.,Gosselin, Francis,Han, Chong,Hildbrand, Stefan,Mack, Kyle A.,Pfaltz, Andreas,Scalone, Michelangelo,Shen, Jeff,Tosatti, Paolo,Zhang, Haiming
, p. 2844 - 2849 (2020/02/05)
Asymmetric hydrogenation has evolved as one of the most powerful tools to construct stereocenters. However, the asymmetric hydrogenation of unfunctionalized tetrasubstituted acyclic olefins remains the pinnacle of asymmetric synthesis and an unsolved challenge. We report herein the discovery of an iridium catalyst for the first, generally applicable, highly enantio- and diastereoselective hydrogenation of such olefins and the mechanistic insights of the reaction. The power of this chemistry is demonstrated by the successful hydrogenation of a wide variety of electronically and sterically diverse olefins in excellent yield and high enantio- and diastereoselectivity.
SnCl4-Zn: A novel reductive system for deoxygenative coupling of aliphatic, aromatic, chalcone epoxide, and indanone carbonyl compounds to olefins
Pathe, Gulab Khushalrao,Ahmed, Naseem
supporting information, p. 1555 - 1561 (2015/03/14)
SnCl4-Zn complex provided a novel reductive system in the deoxygenative cross-coupling of aliphatic, aromatic, chalcone epoxide and indanone carbonyl compounds to olefins in high yield (55-86%) at reflux temperature in THF. The advantage of this reagent is inexpensive, short reaction time, and high yield compared to the reagents used in the McMurry cross-coupling reaction.