Literature DB >> 20433144

Nickel-catalyzed allylic substitution of simple alkenes.

Ryosuke Matsubara1, Timothy F Jamison.   

Abstract

Nickel-catalyzed intermolecular allylic substitution of simple alkenes (ethylene and alpha olefins) is described. This method is the first catalytic intermolecular process for direct allylation of nonconjugated, nonstrained simple alkenes. Catalyst loadings as low as 2.5 mol % Ni afford the desired product in high yield in both gram-scale and smaller scale coupling reactions.

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Year:  2010        PMID： 20433144      PMCID： PMC2893574          DOI： 10.1021/ja101186p

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


  17 in total

1.  New synthetic strategies for the stereocontrolled synthesis of substituted "skipped" diepoxides.

Authors:  Christopher J Morten; Timothy F Jamison
Journal:  Tetrahedron       Date:  2009-08-15       Impact factor: 2.457

2.  Highly selective coupling of alkenes and aldehydes catalyzed by [Ni(NHC){P(OPh)3}]: synergy between a strong sigma donor and a strong pi acceptor.

Authors:  Chun-Yu Ho; Timothy F Jamison
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

3.  Nickel-Catalyzed Coupling Reactions of Alkenes.

Authors:  Sze-Sze Ng; Chun-Yu Ho; Kristin D Schleicher; Timothy F Jamison
Journal:  Pure Appl Chem       Date:  2008       Impact factor: 2.453

4.  Allylic ethers as educts for Suzuki-Miyaura couplings in water at room temperature.

Authors:  Takashi Nishikata; Bruce H Lipshutz
Journal:  J Am Chem Soc       Date:  2009-09-02       Impact factor: 15.419

5.  Simple alkenes as substitutes for organometallic reagents: nickel-catalyzed, intermolecular coupling of aldehydes, silyl triflates, and alpha olefins.

Authors:  Sze-Sze Ng; Timothy F Jamison
Journal:  J Am Chem Soc       Date:  2005-10-19       Impact factor: 15.419

6.  A Theoretical Investigation of the Ni(II)-Catalyzed Hydrovinylation of Styrene.

Authors:  Jorly Joseph; T V Rajanbabu; Eluvathingal D Jemmis
Journal:  Organometallics       Date:  2009-06-22       Impact factor: 3.876

7.  Catalytic Addition of Simple Alkenes to Carbonyl Compounds Using Group 10 Metals.

Authors:  Chun-Yu Ho; Kristin D Schleicher; Timothy F Jamison
Journal:  Synlett       Date:  2009-10-01       Impact factor: 2.454

8.  Nickel-catalyzed synthesis of acrylamides from alpha-olefins and isocyanates.

Authors:  Kristin D Schleicher; Timothy F Jamison
Journal:  Org Lett       Date:  2007-02-02       Impact factor: 6.005

9.  Palladium-catalyzed allylic alkenylation of allylic alcohols with n-butyl acrylate.

Authors:  Naofumi Tsukada; Tetsuo Sato; Yoshio Inoue
Journal:  Chem Commun (Camb)       Date:  2003-10-07       Impact factor: 6.222

10.  Nickel-catalyzed direct conjugate addition of simple alkenes to enones.

Authors:  Sensuke Ogoshi; Toshifumi Haba; Masato Ohashi
Journal:  J Am Chem Soc       Date:  2009-08-05       Impact factor: 15.419
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  19 in total

1.  Nickel-Catalyzed Allylic Alkylation with Diarylmethane Pronucleophiles: Reaction Development and Mechanistic Insights.

Authors:  Sheng-Chun Sha; Hui Jiang; Jianyou Mao; Ana Bellomo; Soo A Jeong; Patrick J Walsh
Journal:  Angew Chem Int Ed Engl       Date:  2015-12-03       Impact factor: 15.336

2.  Nickel-catalyzed Heck-type reactions of benzyl chlorides and simple olefins.

Authors:  Ryosuke Matsubara; Alicia C Gutierrez; Timothy F Jamison
Journal:  J Am Chem Soc       Date:  2011-11-08       Impact factor: 15.419

3.  Nickel Catalysis: Synergy between Method Development and Total Synthesis.

Authors:  Eric A Standley; Sarah Z Tasker; Kim L Jensen; Timothy F Jamison
Journal:  Acc Chem Res       Date:  2015-04-23       Impact factor: 22.384

4.  Ruthenium-Catalyzed C-H Allylation of Alkenes with Allyl Alcohols via C-H Bond Activation in Aqueous Solution.

Authors:  Xiaowei Wu; Haitao Ji
Journal:  J Org Chem       Date:  2018-09-21       Impact factor: 4.354

5.  Nickel-catalyzed Mizoroki-Heck reaction of aryl sulfonates and chlorides with electronically unbiased terminal olefins: high selectivity for branched products.

Authors:  Sarah Z Tasker; Alicia C Gutierrez; Timothy F Jamison
Journal:  Angew Chem Int Ed Engl       Date:  2014-01-08       Impact factor: 15.336

6.  Nickel-catalyzed allylic substitution of simple alkenes.

Authors:  Ryosuke Matsubara; Timothy F Jamison
Journal:  Chem Asian J       Date:  2011-03-08

7.  Scope and Mechanistic Study of the Coupling Reaction of α, β-Unsaturated Carbonyl Compounds with Alkenes: Uncovering Electronic Effects on Alkene Insertion vs Oxidative Coupling Pathways.

Authors:  Ki-Hyeok Kwon; Do W Lee; Chae S Yi
Journal:  Organometallics       Date:  2012-01-09       Impact factor: 3.876

8.  Ethylene in organic synthesis. Repetitive hydrovinylation of alkenes for highly enantioselective syntheses of pseudopterosins.

Authors:  Daniel J Mans; G Adam Cox; T V RajanBabu
Journal:  J Am Chem Soc       Date:  2011-03-30       Impact factor: 15.419

9.  Ni(II) salts and 2-propanol effect catalytic reductive coupling of epoxides and alkynes.

Authors:  Matthew G Beaver; Timothy F Jamison
Journal:  Org Lett       Date:  2011-06-30       Impact factor: 6.005

10.  Mechanistic investigation of the nickel-catalyzed Suzuki reaction of N,O-acetals: evidence for boronic acid assisted oxidative addition and an iminium activation pathway.

Authors:  Kevin T Sylvester; Kevin Wu; Abigail G Doyle
Journal:  J Am Chem Soc       Date:  2012-10-05       Impact factor: 15.419
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