Literature DB >> 22670792

Palladium-catalyzed alkenylation and alkynylation of ortho-C(sp2)-H bonds of benzylamine picolinamides.

Yingsheng Zhao1, Gang He, William A Nack, Gong Chen.   

Abstract

An efficient functionalization of ortho-C(sp(2))-H bonds of picolinamide (PA)-protected benzylamine substrates with a range of vinyl iodides as well as acetylenic bromide is reported. ortho-Phenyl benzoic acid (oPBA) acts as an effective promoter in this reaction system. This method provides a practical strategy to access highly functionalized benzylamine compounds for organic synthesis.

Entities:  

Year:  2012        PMID： 22670792     DOI： 10.1021/ol301214u

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


  6 in total

1.  Palladium-catalyzed C-H functionalization using guanidine as a directing group: ortho arylation and olefination of arylguanidines.

Authors:  Jiaan Shao; Wenteng Chen; Marc A Giulianotti; Richard A Houghten; Yongping Yu
Journal:  Org Lett       Date:  2012-10-24       Impact factor: 6.005

2.  Scope and limitations of auxiliary-assisted, palladium-catalyzed arylation and alkylation of sp2 and sp3 C-H bonds.

Authors:  Enrico T Nadres; Gerson Ivan Franco Santos; Dmitry Shabashov; Olafs Daugulis
Journal:  J Org Chem       Date:  2013-09-19       Impact factor: 4.354

3.  Palladium-catalyzed picolinamide-directed iodination of remote ortho-C-H bonds of arenes: Synthesis of tetrahydroquinolines.

Authors:  William A Nack; Xinmou Wang; Bo Wang; Gang He; Gong Chen
Journal:  Beilstein J Org Chem       Date:  2016-06-17       Impact factor: 2.883

4.  Ligand-assisted palladium-catalyzed C-H alkenylation of aliphatic amines for the synthesis of functionalized pyrrolidines.

Authors:  Chuan He; Matthew J Gaunt
Journal:  Chem Sci       Date:  2017-02-23       Impact factor: 9.825

5.  Picolinamides and Iodoalkynes Enable Palladium-Catalyzed syn-Aminoalkynylation of Di- and Trisubstituted Alkenes to Give Pyrrolidines.

Authors:  Nicolas Müller; Benedikt S Schreib; Sebastian U Leutenegger; Erick M Carreira
Journal:  Angew Chem Int Ed Engl       Date:  2022-05-16       Impact factor: 16.823

6.  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 in total

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