83248-34-4Relevant academic research and scientific papers
Synthesis of Allylboronates via Zweifel-type Deprotonative Olefination
Xu, Nuo,Xu, Jianeng,Zhu, Qing,Liu, Chao
supporting information, p. 2403 - 2407 (2020/12/30)
A method for the synthesis of allylboronates via Zweifel-type deprotonative olefination was demonstrated. Tetrasubstituted vinylboronates were used as the substrates. NCS (N-chlorosuccinimide) was used as a bifunctional additive, electrophile and base. This method exhibited a different elimination strategy in Zweifel type transformation to afford allylboronates. The homo-alcohols and alkenes were stereoselective synthesized from the obtained allylboronates, demonstrating the synthetic value of this methodology. (Figure presented.).
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
supporting information, 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.
Synthesis of polysubstituted olefins by Pd-catalyzed cross-coupling reaction of tosylhydrazones and aryl nonaflates
Barluenga, Jose,Florentino, Lucia,Aznar, Fernando,Valdes, Carlos
supporting information; experimental part, p. 510 - 513 (2011/03/22)
Aryl nonaflates are employed as electrophiles in the Pd-catalyzed cross-coupling with tosylhydrazones affording di-, tri-, and tetrasubstituted olefins. Fine tunning of the reaction conditions are required to accomplish the coupling successfully, includin
Pd-catalyzed oxidative cross-coupling of N-tosylhydrazones with arylboronic acids
Zhao, Xia,Jing, Jing,Lu, Kui,Zhang, Yan,Wang, Jianbo
supporting information; experimental part, p. 1724 - 1726 (2010/07/06)
The Pd-catalyzed reaction of N-tosylhydrazones and arylboronic acids provides olefin derivatives. This oxidative cross-coupling is suggested to proceed through a migratory insertion process of a Pd carbene intermediate.
Vinylation of Aromatic Substrates with Solvolytically Generated Trisubstituted Vinyl Cations
Kitamura, Tsugio,Kobayashi, Shinjiro,Taniguchi, Hiroshi,Rappoport, Zvi
, p. 5003 - 5009 (2007/10/02)
Vinylation of aromatic compounds by α-aryl-β,β-disubstituted vinyl bromides (3a-i) in the presence of silver salts and 2,6-lutidine or 2,6-di-tert-butyl-4-methylpyridine proceed with high yields.The silver triflate assisted reaction is preferable to the silver tetrafluoroborate assisted reaction.The reaction of 1-anisyl-2,2-diphenylvinyl bromide gives a ρ+ value of -4.08 and high intramolecular selectivity with ko/kp ratios of 6.2-78.It is suggested that the reaction proceeds via intermediate α-arylvinyl cations and that the inter- and intramolecular selectivities are determined in the same transition state.
