Literature DB >> 20704415

Copper-catalyzed synthesis of phenanthridine derivatives under an oxygen atmosphere starting from biaryl-2-carbonitriles and Grignard reagents.

Line Zhang1, Gim Yean Ang, Shunsuke Chiba.   

Abstract

A copper-catalyzed synthesis of phenanthridine derivatives was developed starting from biaryl-2-carbonitriles and Grignard reagents. The present transformation is carried out by a sequence of nucleophilic addition of Grignard reagents to biaryl-2-carbonitriles to form N-H imines and their Cu-catalyzed C-N bond formation on the aromatic C-H bond, where molecular oxygen is a prerequisite to achieve the catalytic process.

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Year:  2010        PMID: 20704415     DOI: 10.1021/ol101490n

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


  7 in total

Review 1.  Aerobic copper-catalyzed organic reactions.

Authors:  Scott E Allen; Ryan R Walvoord; Rosaura Padilla-Salinas; Marisa C Kozlowski
Journal:  Chem Rev       Date:  2013-06-20       Impact factor: 60.622

2.  Copper-catalyzed oxidative amination and allylic amination of alkenes.

Authors:  Timothy W Liwosz; Sherry R Chemler
Journal:  Chemistry       Date:  2013-07-22       Impact factor: 5.236

Review 3.  Photocatalyzed syntheses of phenanthrenes and their aza-analogues. A review.

Authors:  Alessandra Del Tito; Havall Othman Abdulla; Davide Ravelli; Stefano Protti; Maurizio Fagnoni
Journal:  Beilstein J Org Chem       Date:  2020-06-25       Impact factor: 2.883

4.  Cu(OAc)2 catalysed aerobic oxidation of aldehydes to nitriles under ligand-free conditions.

Authors:  Asit Kumar Das; Sneha Nandy; Sanjay Bhar
Journal:  RSC Adv       Date:  2022-02-04       Impact factor: 3.361

5.  Synthesis of phenanthridines via palladium-catalyzed picolinamide-directed sequential C-H functionalization.

Authors:  Ryan Pearson; Shuyu Zhang; Gang He; Nicola Edwards; Gong Chen
Journal:  Beilstein J Org Chem       Date:  2013-05-08       Impact factor: 2.883

6.  Copper-catalyzed aerobic radical C-C bond cleavage of N-H ketimines.

Authors:  Ya Lin Tnay; Gim Yean Ang; Shunsuke Chiba
Journal:  Beilstein J Org Chem       Date:  2015-10-19       Impact factor: 2.883

7.  Pivalophenone imine as a benzonitrile surrogate for directed C-H bond functionalization.

Authors:  Wengang Xu; Naohiko Yoshikai
Journal:  Chem Sci       Date:  2017-05-30       Impact factor: 9.825

  7 in total

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