Literature DB >> 26493363

Dioxygen-Mediated Decarbonylative C-H Alkylation of Heteroaromatic Bases with Aldehydes.

Subhasis Paul1, Joyram Guin2.   

Abstract

An operationally simple and economical method for the direct alkylation of heteroaromatic bases employing readily available aldehydes as alkyl radical precursors and molecular oxygen as a reagent is presented. This simple transformation demonstrates a broad substrate scope with respect to aldehydes and nitrogen heterocycles, enabling the introduction of several medicinally important yet challenging alkyl moieties, such as ethyl, isopropyl, tert-butyl, and cyclohexyl to the different classes of heterocyclic bases in good to excellent yields.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  CH functionalization; auto-oxidation; heterocycles; oxygen; radical reactions

Year:  2015        PMID: 26493363     DOI: 10.1002/chem.201503809

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  10 in total

1.  Late-Stage C-H Alkylation of Heterocycles and 1,4-Quinones via Oxidative Homolysis of 1,4-Dihydropyridines.

Authors:  Álvaro Gutiérrez-Bonet; Camille Remeur; Jennifer K Matsui; Gary A Molander
Journal:  J Am Chem Soc       Date:  2017-08-23       Impact factor: 15.419

2.  Oxidase catalysis via aerobically generated hypervalent iodine intermediates.

Authors:  Asim Maity; Sung-Min Hyun; David C Powers
Journal:  Nat Chem       Date:  2017-10-16       Impact factor: 24.427

3.  Synthesis of Alkyl Halides from Aldehydes via Deformylative Halogenation.

Authors:  Shengzong Liang; Tatsuya Kumon; Ricardo A Angnes; Melissa Sanchez; Bo Xu; Gerald B Hammond
Journal:  Org Lett       Date:  2019-05-03       Impact factor: 6.005

4.  Catalyst-Free Decarbonylative Trifluoromethylthiolation Enabled by Electron Donor-Acceptor Complex Photoactivation.

Authors:  Alexander Lipp; Shorouk O Badir; Ryan Dykstra; Osvaldo Gutierrez; Gary A Molander
Journal:  Adv Synth Catal       Date:  2021-05-19       Impact factor: 5.981

5.  The photochemical alkylation and reduction of heteroarenes.

Authors:  T McCallum; S P Pitre; M Morin; J C Scaiano; L Barriault
Journal:  Chem Sci       Date:  2017-09-11       Impact factor: 9.825

6.  Direct alkylation of heteroarenes with unactivated bromoalkanes using photoredox gold catalysis.

Authors:  T McCallum; L Barriault
Journal:  Chem Sci       Date:  2016-04-18       Impact factor: 9.825

7.  Ketones and aldehydes as alkyl radical equivalents for C─H functionalization of heteroarenes.

Authors:  Jianyang Dong; Zhen Wang; Xiaochen Wang; Hongjian Song; Yuxiu Liu; Qingmin Wang
Journal:  Sci Adv       Date:  2019-10-11       Impact factor: 14.957

8.  Autoxidation of Formaldehyde with Oxygen-A Comparison of Reaction Channels.

Authors:  Sandhiya Lakshmanan; Niranjanmurthi Lingappan
Journal:  ACS Omega       Date:  2022-02-18

9.  A Visible Light-Driven Minisci-Type Reaction with N-Hydroxyphthalimide Esters.

Authors:  Lisa Marie Kammer; Aliyaah Rahman; Till Opatz
Journal:  Molecules       Date:  2018-03-27       Impact factor: 4.411

10.  Fe-catalyzed Decarbonylative Alkylative Spirocyclization of N-Arylcinnamamides: Access to Alkylated 1-Azaspirocyclohexadienones.

Authors:  Xiang Peng; Ren-Xiang Liu; Xiang-Yan Xiao; Luo Yang
Journal:  Molecules       Date:  2020-01-21       Impact factor: 4.411

  10 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.