Literature DB >> 28835962

Palladium-catalysed alkene chain-running isomerization.

Andrew L Kocen1, Maurice Brookhart, Olafs Daugulis.   

Abstract

We report a method for palladium-catalysed chain-running isomerization of terminal and internal alkenes. Using an air-stable 2,9-dimethylphenanthroline-palladium catalyst in combination with NaBAr4 promoter, olefins are converted to the most stable double bond isomer at -30 to 20 °C. Silyl enol ethers are readily formed from silylated allylic alcohols. Fluorinated substituents are compatible with the reaction conditions, allowing the synthesis of fluoroenolates. Catalyst loading as low as 0.05% can be employed on a gram scale.

Entities:  

Year:  2017        PMID： 28835962      PMCID： PMC5705238          DOI： 10.1039/c7cc04953f

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  35 in total

1.  Stereochemical Control in Organic Synthesis Using Silicon-Containing Compounds.

Authors:  Ian Fleming; Asuncion Barbero; David Walter
Journal:  Chem Rev       Date:  1997-10-01       Impact factor: 60.622

2.  Rhodium catalyzed chelation-assisted C-H bond functionalization reactions.

Authors:  Denise A Colby; Andy S Tsai; Robert G Bergman; Jonathan A Ellman
Journal:  Acc Chem Res       Date:  2011-12-08       Impact factor: 22.384

3.  Palladium-Catalyzed Long-Range Deconjugative Isomerization of Highly Substituted α,β-Unsaturated Carbonyl Compounds.

Authors:  Luqing Lin; Ciro Romano; Clément Mazet
Journal:  J Am Chem Soc       Date:  2016-08-02       Impact factor: 15.419

4.  Remote carboxylation of halogenated aliphatic hydrocarbons with carbon dioxide.

Authors:  Francisco Juliá-Hernández; Toni Moragas; Josep Cornella; Ruben Martin
Journal:  Nature       Date:  2017-05-03       Impact factor: 49.962

5.  Synthesis of Z-alkenes from Rh(I)-catalyzed olefin isomerization of β,γ-unsaturated ketones.

Authors:  Lian-Gang Zhuo; Zhong-Ke Yao; Zhi-Xiang Yu
Journal:  Org Lett       Date:  2013-09-04       Impact factor: 6.005

6.  Supported imidazolylphosphine catalysts for highly (E)-selective alkene isomerization.

Authors:  Gulin Erdogan; Douglas B Grotjahn
Journal:  Org Lett       Date:  2014-05-08       Impact factor: 6.005

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

Authors:  Casey R Larsen; Gulin Erdogan; Douglas B Grotjahn
Journal:  J Am Chem Soc       Date:  2014-01-14       Impact factor: 15.419

8.  Activator-free olefin oligomerization and isomerization reactions catalyzed by an air- and water-tolerant Wacker oxidation intermediate.

Authors:  Matthew S Winston; Paul F Oblad; Jay A Labinger; John E Bercaw
Journal:  Angew Chem Int Ed Engl       Date:  2012-09-03       Impact factor: 15.336

9.  Michael Addition Catalyzed by Chiral Secondary Amine Phosphoramide Using Fluorinated Silyl Enol Ethers: Formation of Quaternary Carbon Stereocenters.

Authors:  Jin-Sheng Yu; Fu-Min Liao; Wei-Ming Gao; Kui Liao; Run-Lin Zuo; Jian Zhou
Journal:  Angew Chem Int Ed Engl       Date:  2015-05-07       Impact factor: 15.336

10.  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
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  1 in total

1.  Regioselectivity Influences in Platinum-Catalyzed Intramolecular Alkyne O-H and N-H Additions.

Authors:  Jeff P Costello; Eric M Ferreira
Journal:  Org Lett       Date:  2019-12-09       Impact factor: 6.072
  1 in total

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