Literature DB >> 25000283

Palladium-catalyzed C8 alkylation of 1-naphthylamides with alkyl halides via bidentate-chelation assistance.

Lehao Huang1, Xudong Sun, Qian Li, Chenze Qi.   

Abstract

A Pd-catalyzed regioselective alkylation of C8-H bonds in 1-naphthylamides containing a quinolinamide or picolinamide moiety as a bidentate directing group with alkyl halides is reported. The amide directing group can be easily hydrolyzed under basic conditions. Various alkyl halides including alkyl iodides and benzyl bromide or chloride can be employed as coupling partners, exclusively providing 8-alkyl-1-naphthylamide derivatives.

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Year:  2014        PMID: 25000283     DOI: 10.1021/jo500932x

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


  3 in total

1.  Iridium-Catalyzed, Silyl-Directed, peri-Borylation of C-H Bonds in Fused Polycyclic Arenes and Heteroarenes.

Authors:  Bo Su; John F Hartwig
Journal:  Angew Chem Int Ed Engl       Date:  2018-07-13       Impact factor: 15.336

2.  Overcoming peri- and ortho-selectivity in C-H methylation of 1-naphthaldehydes by a tunable transient ligand strategy.

Authors:  Yujian Mao; Jing Jiang; Dandan Yuan; Xiuzhen Chen; Yanan Wang; Lihong Hu; Yinan Zhang
Journal:  Chem Sci       Date:  2022-01-06       Impact factor: 9.825

3.  Ruthenium-Catalyzed Peri- and Ortho-Alkynylation with Bromoalkynes via Insertion and Elimination.

Authors:  Eric Tan; Andrey I Konovalov; Gabriela A Fernández; Ruth Dorel; Antonio M Echavarren
Journal:  Org Lett       Date:  2017-10-04       Impact factor: 6.005

  3 in total

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