Literature DB >> 34881902

Synthesis of α-Branched Amines by Three- and Four-Component C-H Functionalization Employing a Readily Diversifiable Hydrazone Directing Group.

Daniel S Brandes1, Alex D Muma1, Jonathan A Ellman1.   

Abstract

Efficient syntheses of α-branched amines by three- and four-component C-H functionalization employing a diversifiable hydrazone directing group have been developed. The hydrazone in the α-branched amine products has been readily converted to multiple desirable functionalities such as a nitrile, a carboxylic acid, alkenes, and heterocycles using diverse heterolytic chemistry and homolytic transition metal- or photoredox-catalyzed processes. This study represents the first example of a four-component C-H functionalization reaction.

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Year:  2021        PMID: 34881902      PMCID: PMC8785212          DOI: 10.1021/acs.orglett.1c03807

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


  9 in total

1.  Aza-Conjugate Addition Methodology for the Synthesis of N-Hydroxy-isoindolin-1-ones.

Authors:  Santiago Royo; Robert S L Chapman; Alisia M Sim; Lucy R Peacock; Steven D Bull
Journal:  Org Lett       Date:  2016-02-22       Impact factor: 6.005

2.  [3+2] Cycloaddition of azide with aldehyde hydrazone through an aminyl radical-polar crossover strategy.

Authors:  Zhongkai Wu; Pan Xu; Nengneng Zhou; Yingqian Duan; Muliang Zhang; Chengjian Zhu
Journal:  Chem Commun (Camb)       Date:  2017-01-17       Impact factor: 6.222

3.  Highly Stereoselective Cobalt(III)-Catalyzed Three-Component C-H Bond Addition Cascade.

Authors:  Jeffrey A Boerth; Joshua R Hummel; Jonathan A Ellman
Journal:  Angew Chem Int Ed Engl       Date:  2016-06-15       Impact factor: 15.336

4.  Three-Component Ruthenium-Catalyzed Direct Meta-Selective C-H Activation of Arenes: A New Approach to the Alkylarylation of Alkenes.

Authors:  Xin-Gang Wang; Yuke Li; Hong-Chao Liu; Bo-Sheng Zhang; Xue-Ya Gou; Qiang Wang; Jun-Wei Ma; Yong-Min Liang
Journal:  J Am Chem Soc       Date:  2019-08-20       Impact factor: 15.419

5.  Exploration of C-H Transformations of Aldehyde Hydrazones: Radical Strategies and Beyond.

Authors:  Pan Xu; Weipeng Li; Jin Xie; Chengjian Zhu
Journal:  Acc Chem Res       Date:  2018-01-23       Impact factor: 22.384

6.  Relay Visible-Light Photoredox Catalysis: Synthesis of Pyrazole Derivatives via Formal [4 + 1] Annulation and Aromatization.

Authors:  Jian Cheng; Weipeng Li; Yingqian Duan; Yixiang Cheng; Shouyun Yu; Chengjian Zhu
Journal:  Org Lett       Date:  2016-12-20       Impact factor: 6.005

7.  Palladium-catalyzed C-H activation/intramolecular amination reaction: a new route to 3-aryl/alkylindazoles.

Authors:  Kiyofumi Inamoto; Tadataka Saito; Mika Katsuno; Takao Sakamoto; Kou Hiroya
Journal:  Org Lett       Date:  2007-06-27       Impact factor: 6.005

8.  Rh(III)-Catalyzed Diastereoselective C-H Bond Addition/Cyclization Cascade of Enone Tethered Aldehydes.

Authors:  Jeffrey A Boerth; Jonathan A Ellman
Journal:  Chem Sci       Date:  2015-12-01       Impact factor: 9.825

9.  Sequential Catalytic Functionalization of Aryltriazenyl Aldehydes for the Synthesis of Complex Benzenes.

Authors:  Sangwon Seo; Ming Gao; Eva Paffenholz; Michael C Willis
Journal:  ACS Catal       Date:  2021-05-05       Impact factor: 13.084

  9 in total
  2 in total

Review 1.  C-H bond activation and sequential addition to two different coupling partners: a versatile approach to molecular complexity.

Authors:  Daniel S Brandes; Jonathan A Ellman
Journal:  Chem Soc Rev       Date:  2022-08-01       Impact factor: 60.615

2.  Stereoselective Synthesis of Allenyl Alcohols by Cobalt(III)-Catalyzed Sequential C-H Bond Addition to 1,3-Enynes and Aldehydes.

Authors:  Chaofan Xu; Joseph P Tassone; Brandon Q Mercado; Jonathan A Ellman
Journal:  Angew Chem Int Ed Engl       Date:  2022-04-29       Impact factor: 16.823

  2 in total

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