Literature DB >> 31050440

Synthesis of Alkyl Halides from Aldehydes via Deformylative Halogenation.

Shengzong Liang1, Tatsuya Kumon2, Ricardo A Angnes3, Melissa Sanchez4, Bo Xu5, Gerald B Hammond1.   

Abstract

An unprecedented deformylative halogenation of aldehydes to alkyl halides is presented. Under oxidative conditions, 1,4-dihydropyridine (DHP), derived from an aldehyde, generated a C(sp3)- radical that coupled with a halogen radical that was generated from inexpensive and atom-economical halogen sources (NaBr, NaI, or HCl), to yield an alkyl halide. Because of the mild conditions, a wide range of functional groups were tolerated, and excellent site selectivity was achieved.

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Year:  2019        PMID： 31050440      PMCID： PMC6525078          DOI： 10.1021/acs.orglett.9b01337

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


  87 in total

Review 1.  Halogen atoms in the modern medicinal chemistry: hints for the drug design.

Authors:  Marcelo Zaldini Hernandes; Suellen Melo T Cavalcanti; Diogo Rodrigo M Moreira; Walter Filgueira de Azevedo Junior; Ana Cristina Lima Leite
Journal:  Curr Drug Targets       Date:  2010-03       Impact factor: 3.465

2.  Direct Aldehyde C-H Arylation and Alkylation via the Combination of Nickel, Hydrogen Atom Transfer, and Photoredox Catalysis.

Authors:  Xiaheng Zhang; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2017-08-14       Impact factor: 15.419

3.  Synthesis of Non-Classical Arylated C-Saccharides through Nickel/Photoredox Dual Catalysis.

Authors:  Audrey Dumoulin; Jennifer K Matsui; Álvaro Gutiérrez-Bonet; Gary A Molander
Journal:  Angew Chem Int Ed Engl       Date:  2018-04-14       Impact factor: 15.336

4.  Site-selective aliphatic C-H bromination using N-bromoamides and visible light.

Authors:  Valerie A Schmidt; Ryan K Quinn; Andrew T Brusoe; Erik J Alexanian
Journal:  J Am Chem Soc       Date:  2014-10-03       Impact factor: 15.419

5.  Isolable and Readily Handled Halophosphonium Pre-reagents for Hydro- and Deuteriohalogenation.

Authors:  Florian T Schevenels; Minxing Shen; Scott A Snyder
Journal:  J Am Chem Soc       Date:  2017-05-02       Impact factor: 15.419

6.  Silver-Catalyzed Decarboxylative Bromination of Aliphatic Carboxylic Acids.

Authors:  Xinqiang Tan; Tao Song; Zhentao Wang; He Chen; Lei Cui; Chaozhong Li
Journal:  Org Lett       Date:  2017-03-13       Impact factor: 6.005

7.  Oxidative halogenation with "green" oxidants: oxygen and hydrogen peroxide.

Authors:  Ajda Podgorsek; Marko Zupan; Jernej Iskra
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

Review 8.  Recent advances in homogeneous nickel catalysis.

Authors:  Sarah Z Tasker; Eric A Standley; Timothy F Jamison
Journal:  Nature       Date:  2014-05-15       Impact factor: 49.962

9.  1,4-Dihydropyridines as Alkyl Radical Precursors: Introducing the Aldehyde Feedstock to Nickel/Photoredox Dual Catalysis.

Authors:  Álvaro Gutiérrez-Bonet; John C Tellis; Jennifer K Matsui; Brandon A Vara; Gary A Molander
Journal:  ACS Catal       Date:  2016-10-27       Impact factor: 13.084

10.  Bromination of hydrocarbons with CBr4, initiated by light-emitting diode irradiation.

Authors:  Yuta Nishina; Bunsho Ohtani; Kotaro Kikushima
Journal:  Beilstein J Org Chem       Date:  2013-08-14       Impact factor: 2.883
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  1 in total

1.  Theoretical investigation on the nature of 4-substituted Hantzsch esters as alkylation agents.

Authors:  Guang-Bin Shen; Li Xie; Hao-Yun Yu; Jie Liu; Yan-Hua Fu; Maocai Yan
Journal:  RSC Adv       Date:  2020-08-25       Impact factor: 4.036
  1 in total

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