Literature DB >> 18778055

Intramolecular arylcyanation of alkenes catalyzed by nickel/AlMe2Cl.

Yoshiaki Nakao1, Shiro Ebata, Akira Yada, Tamejiro Hiyama, Masashi Ikawa, Sensuke Ogoshi.   

Abstract

A catalyst system derived from nickel and cocatalytic AlMe2Cl effects the intramolecular arylcyanation of alkenes. The reaction takes place in an exclusive exo-dig manner to give a wide range of nitriles having a benzylic quaternary carbon in good yields. Detailed investigations are described on the scope and mechanism as well as preliminary results on the asymmetric version of the reaction to provide novel access to chiral quaternary stereocenters.

Entities:  

Year:  2008        PMID： 18778055     DOI： 10.1021/ja805088r

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


  20 in total

1.  Palladium catalyzed intramolecular acylcyanation of alkenes using α-iminonitriles.

Authors:  Naveen R Rondla; Jodi M Ogilvie; Zhongda Pan; Christopher J Douglas
Journal:  Chem Commun (Camb)       Date:  2014-08-18       Impact factor: 6.222

2.  Further Developments and Applications of Oxazoline-Containing Ligands in Asymmetric Catalysis.

Authors:  Robert Connon; Brendan Roche; Balaji V Rokade; Patrick J Guiry
Journal:  Chem Rev       Date:  2021-05-21       Impact factor: 60.622

3.  Diastereoselective Intramolecular Cyanoamidation with Alkenes.

Authors:  Ashley M Dreis; Sadie C Otte; Matthew S Eastwood; Elizabeth R Alonzi; Jason T Brethorst; Christopher J Douglas
Journal:  European J Org Chem       Date:  2016-12-13

4.  Kinetic Resolution via Rh-Catalyzed C-C Activation of Cyclobutanones at Room Temperature.

Authors:  Lin Deng; Yue Fu; Siu Yin Lee; Chengpeng Wang; Peng Liu; Guangbin Dong
Journal:  J Am Chem Soc       Date:  2019-10-02       Impact factor: 15.419

5.  Ethylene in organic synthesis: a new route to anticholenergic pyrrolidinoindolines, and other molecules with all carbon-quaternary centers via asymmetric hydrovinylation.

Authors:  Hwan Jung Lim; T V RajanBabu
Journal:  Org Lett       Date:  2011-11-21       Impact factor: 6.005

6.  Mechanistic Model for Enantioselective Intramolecular Alkene Cyanoamidation via Palladium-Catalyzed C-CN Bond Activation.

Authors:  Grant B Frost; Nicholas A Serratore; Jodi M Ogilvie; Christopher J Douglas
Journal:  J Org Chem       Date:  2017-03-15       Impact factor: 4.354

7.  Coupling of sterically hindered trisubstituted olefins and benzocyclobutenones by C-C activation: total synthesis and structural revision of cycloinumakiol.

Authors:  Tao Xu; Guangbin Dong
Journal:  Angew Chem Int Ed Engl       Date:  2014-08-19       Impact factor: 15.336

8.  Transition Metals Catalyzed Element-Cyano Bonds Activations.

Authors:  Rui Wang; John R Falck
Journal:  Catal Rev Sci Eng       Date:  2014-07       Impact factor: 20.217

9.  Recent developments in the catalytic, asymmetric construction of pyrroloindolines bearing all-carbon quaternary stereocenters.

Authors:  Lindsay M Repka; Sarah E Reisman
Journal:  J Org Chem       Date:  2013-12-02       Impact factor: 4.354

10.  "Cut and Sew" Transformations via Transition-Metal-Catalyzed Carbon-Carbon Bond Activation.

Authors:  Peng-Hao Chen; Brent A Billett; Tatsuhiro Tsukamoto; Guangbin Dong
Journal:  ACS Catal       Date:  2017-01-06       Impact factor: 13.084
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