Literature DB >> 24422470

General catalyst control of the monoisomerization of 1-alkenes to trans-2-alkenes.

Casey R Larsen1, Gulin Erdogan, Douglas B Grotjahn.   

Abstract

After searching for the proper catalyst, the dual challenges of controlling the position of the double bond, and cis/trans-selectivity in isomerization of terminal alkenes to their 2-isomers are finally met in a general sense by mixtures of (C5Me5)Ru complexes 1 and 3 featuring a bifunctional phosphine. Typically, catalyst loadings of 1 mol % of 1 and 3 can be employed for the production of (E)-2-alkenes at 40-70 °C. Catalyst comprising 1 and 3 avoids more than any other known example the thermodynamic equilibration of alkene isomers, as the trans-2-alkenes of both nonfunctionalized and functionalized alkenes are generated.

Entities:  

Year:  2014        PMID: 24422470     DOI: 10.1021/ja411438d

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  12 in total

1.  Palladium-catalysed alkene chain-running isomerization.

Authors:  Andrew L Kocen; Maurice Brookhart; Olafs Daugulis
Journal:  Chem Commun (Camb)       Date:  2017-09-05       Impact factor: 6.222

2.  Parts-per-million of ruthenium catalyze the selective chain-walking reaction of terminal alkenes.

Authors:  Sergio Sanz-Navarro; Marta Mon; Antonio Doménech-Carbó; Rossella Greco; Jorge Sánchez-Quesada; Estela Espinós-Ferri; Antonio Leyva-Pérez
Journal:  Nat Commun       Date:  2022-05-20       Impact factor: 17.694

3.  Highly Z-Selective Double Bond Transposition in Simple Alkenes and Allylarenes through a Spin-Accelerated Allyl Mechanism.

Authors:  Daniel Kim; Guy Pillon; Daniel J DiPrimio; Patrick L Holland
Journal:  J Am Chem Soc       Date:  2021-02-17       Impact factor: 15.419

4.  Isomerization of Olefins Triggered by Rhodium-Catalyzed C-H Bond Activation: Control of Endocyclic β-Hydrogen Elimination.

Authors:  Stephanie Y Y Yip; Christophe Aïssa
Journal:  Angew Chem Int Ed Engl       Date:  2015-04-23       Impact factor: 15.336

5.  Nickel-catalysed retro-hydroamidocarbonylation of aliphatic amides to olefins.

Authors:  Jiefeng Hu; Minyan Wang; Xinghui Pu; Zhuangzhi Shi
Journal:  Nat Commun       Date:  2017-05-05       Impact factor: 14.919

6.  Remote functionalization of hydrocarbons with reversibility enhanced stereocontrol.

Authors:  Alexandre Vasseur; Lionel Perrin; Odile Eisenstein; Ilan Marek
Journal:  Chem Sci       Date:  2015-03-03       Impact factor: 9.825

7.  Pillar[3]trianglamines: deeper cavity triangular macrocycles for selective hexene isomer separation.

Authors:  Yanjun Ding; Lukman O Alimi; Jing Du; Bin Hua; Avishek Dey; Pei Yu; Niveen M Khashab
Journal:  Chem Sci       Date:  2022-03-02       Impact factor: 9.825

8.  Highly selective acid-catalyzed olefin isomerization of limonene to terpinolene by kinetic suppression of overreactions in a confined space of porous metal-macrocycle frameworks.

Authors:  Wei He; Shohei Tashiro; Mitsuhiko Shionoya
Journal:  Chem Sci       Date:  2022-06-03       Impact factor: 9.969

9.  Palladium hydride promoted stereoselective isomerization of unactivated di(exo)methylenes to endocyclic dienes.

Authors:  Michael E Jung; Gloria S Lee; Hung V Pham; K N Houk
Journal:  Org Lett       Date:  2014-04-11       Impact factor: 6.005

10.  Controllable Isomerization of Alkenes by Dual Visible-Light-Cobalt Catalysis.

Authors:  Qing-Yuan Meng; Tobias E Schirmer; Kousuke Katou; Burkhard König
Journal:  Angew Chem Int Ed Engl       Date:  2019-03-26       Impact factor: 15.336

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