Literature DB >> 23259673

Annulation of α,β-unsaturated imines and alkynes via cobalt-catalyzed olefinic C-H activation.

Takeshi Yamakawa1, Naohiko Yoshikai.   

Abstract

A cobalt-triarylphosphine catalyst promotes an annulation reaction of an α,β-unsaturated imine and an internal alkyne to afford a polysubstituted dihydropyridine derivative in good yield under mild conditions. The reaction likely involves alkenylation of the olefinic C-H bond via cobalt-mediated nitrogen-assisted C-H activation followed by facile 6π electrocyclization of the resulting azatriene intermediate.

Entities:  

Year:  2012        PMID: 23259673     DOI: 10.1021/ol303259m

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  6 in total

1.  Cobalt-catalyzed, aminoquinoline-directed C(sp²)-H bond alkenylation by alkynes.

Authors:  Liene Grigorjeva; Olafs Daugulis
Journal:  Angew Chem Int Ed Engl       Date:  2014-07-24       Impact factor: 15.336

2.  Regio- and stereoselective 1,2-dihydropyridine alkylation/addition sequence for the synthesis of piperidines with quaternary centers.

Authors:  Simon Duttwyler; Shuming Chen; Colin Lu; Brandon Q Mercado; Robert G Bergman; Jonathan A Ellman
Journal:  Angew Chem Int Ed Engl       Date:  2014-03-06       Impact factor: 15.336

3.  Cobalt-Catalyzed, Aminoquinoline-Directed Functionalization of Phosphinic Amide sp2 C-H Bonds.

Authors:  Tung Thanh Nguyen; Liene Grigorjeva; Olafs Daugulis
Journal:  ACS Catal       Date:  2015-12-22       Impact factor: 13.084

4.  Copper-catalyzed condensation of imines and α-diazo-β-dicarbonyl compounds: modular and regiocontrolled synthesis of multisubstituted pyrroles.

Authors:  Wei Wen Tan; Naohiko Yoshikai
Journal:  Chem Sci       Date:  2015-08-03       Impact factor: 9.825

Review 5.  Convergent Synthesis of Diverse Tetrahydropyridines via Rh(I)-Catalyzed C-H Functionalization Sequences.

Authors:  Tehetena Mesganaw; Jonathan A Ellman
Journal:  Org Process Res Dev       Date:  2014-08-29       Impact factor: 3.317

6.  Cobalt(III)-catalyzed synthesis of indazoles and furans by C-H bond functionalization/addition/cyclization cascades.

Authors:  Joshua R Hummel; Jonathan A Ellman
Journal:  J Am Chem Soc       Date:  2014-12-24       Impact factor: 15.419

  6 in total

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