Literature DB >> 23570365

Anti carbocyanative cyclization of enynes under nickel catalysis.

Tomohiro Igarashi1, Shigeru Arai, Atsushi Nishida.   

Abstract

Anti carbocyanative cyclization using 1,6-enynes under nickel catalysis is described. This reaction is triggered by hydronickelation to alkenes followed by carbometalation. Steric repulsion caused by the bulky substituents on alkynes promotes isomerization of the carbon-carbon double bond geometry in an organonickel intermediate to introduce both alkyl and cyano groups in an anti fashion.

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Year:  2013        PMID: 23570365     DOI: 10.1021/jo400342y

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  5 in total

1.  Rapid access to t-butylalkylated olefins enabled by Ni-catalyzed intermolecular regio- and trans-selective cross-electrophile t-butylalkylation of alkynes.

Authors:  Yi-Zhou Zhan; Huan Meng; Wei Shu
Journal:  Chem Sci       Date:  2022-03-30       Impact factor: 9.969

Review 2.  Direct cyanation, hydrocyanation, dicyanation and cyanofunctionalization of alkynes.

Authors:  Lifen Peng; Zhifang Hu; Hong Wang; Li Wu; Yinchun Jiao; Zilong Tang; Xinhua Xu
Journal:  RSC Adv       Date:  2020-03-10       Impact factor: 4.036

3.  Enantioselective Nickel-Catalyzed anti-Arylmetallative Cyclizations onto Acyclic Ketones.

Authors:  Harley Green; Stephen P Argent; Hon Wai Lam
Journal:  Chemistry       Date:  2021-03-05       Impact factor: 5.236

Review 4.  Nickel-Catalyzed Arylative Cyclizations of Alkyne- and Allene-Tethered Electrophiles using Arylboron Reagents.

Authors:  Simone M Gillbard; Hon Wai Lam
Journal:  Chemistry       Date:  2022-01-27       Impact factor: 5.020

5.  Enantioselective Synthesis of Chiral Cyclopent-2-enones by Nickel-Catalyzed Desymmetrization of Malonate Esters.

Authors:  Somnath Narayan Karad; Heena Panchal; Christopher Clarke; William Lewis; Hon Wai Lam
Journal:  Angew Chem Int Ed Engl       Date:  2018-06-19       Impact factor: 15.336

  5 in total

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