Literature DB >> 20196596

Palladium-catalyzed benzylic addition of 2-methyl azaarenes to N-sulfonyl aldimines via C-H bond activation.

Bo Qian1, Shengmei Guo, Jianping Shao, Qiming Zhu, Lei Yang, Chungu Xia, Hanmin Huang.   

Abstract

An efficient protocol for the generation of amines by palladium-catalyzed nucleophilic benzylic addition of 2-methyl-substituted azaarenes to N-sulfonyl aldimines under neutral conditions via C-H bond activation has been developed. This reaction represents a very efficient methodology for the synthesis of heterocycle-containing amines and thus opens a new way to access amines through C-H bond activation.

Entities:  

Year:  2010        PMID： 20196596     DOI： 10.1021/ja910104n

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  10 in total

1.  Rhodium(III)-catalyzed arylation of Boc-imines via C-H bond functionalization.

Authors:  Andy S Tsai; Michael E Tauchert; Robert G Bergman; Jonathan A Ellman
Journal:  J Am Chem Soc       Date:  2011-01-04       Impact factor: 15.419

2.  Rhodium-catalyzed synthesis of branched amines by direct addition of benzamides to imines.

Authors:  Kevin D Hesp; Robert G Bergman; Jonathan A Ellman
Journal:  Org Lett       Date:  2012-04-13       Impact factor: 6.005

3.  Transition-Metal-Catalyzed C-H Bond Addition to Carbonyls, Imines, and Related Polarized π Bonds.

Authors:  Joshua R Hummel; Jeffrey A Boerth; Jonathan A Ellman
Journal:  Chem Rev       Date:  2016-12-12       Impact factor: 60.622

4.  Convergent Synthesis of α-Branched Amines by Transition-Metal-Catalyzed C-H Bond Additions to Imines.

Authors:  Joshua R Hummel; Jonathan A Ellman
Journal:  Isr J Chem       Date:  2017-06-29       Impact factor: 3.333

5.  Palladium-Catalyzed Benzylic Arylation of Pyridylmethyl Silyl Ethers: One-Pot Synthesis of Aryl(pyridyl)methanols.

Authors:  Alexandra R Rivero; Byeong-Seon Kim; Patrick J Walsh
Journal:  Org Lett       Date:  2016-03-23       Impact factor: 6.005

6.  Chemoselective Palladium-Catalyzed Deprotonative Arylation/[1,2]-Wittig Rearrangement of Pyridylmethyl Ethers.

Authors:  Feng Gao; Byeong-Seon Kim; Patrick J Walsh
Journal:  Chem Sci       Date:  2015-10-27       Impact factor: 9.825

7.  A highly site-selective radical sp3 C-H amination of azaheterocycles.

Authors:  Keith W Bentley; Krysta A Dummit; Jeffrey F Van Humbeck
Journal:  Chem Sci       Date:  2018-07-10       Impact factor: 9.825

8.  An atom-economical addition of methyl azaarenes with aromatic aldehydes via benzylic C(sp3)-H bond functionalization under solvent- and catalyst-free conditions.

Authors:  Divya Rohini Yennamaneni; Vasu Amrutham; Krishna Sai Gajula; Rammurthy Banothu; Murali Boosa; Narender Nama
Journal:  Beilstein J Org Chem       Date:  2020-12-23       Impact factor: 2.883

9.  Pyridylic anions are soft nucleophiles in the palladium-catalyzed C(sp3)-H allylation of 4-alkylpyridines.

Authors:  Nour Wasfy; Faizan Rasheed; Raphaël Robidas; Isabelle Hunter; Jiaqi Shi; Brian Doan; Claude Y Legault; Dan Fishlock; Arturo Orellana
Journal:  Chem Sci       Date:  2020-12-10       Impact factor: 9.825

10.  Acetic Acid Promoted Redox Annulations with Dual C-H Functionalization.

Authors:  Zhengbo Zhu; Daniel Seidel
Journal:  Org Lett       Date:  2017-05-16       Impact factor: 6.005
  10 in total

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