Literature DB >> 28230308

Iron-Catalyzed Decarboxylative Alkyl Etherification of Vinylarenes with Aliphatic Acids as the Alkyl Source.

Wujun Jian1, Liang Ge1, Yihang Jiao1, Bo Qian1, Hongli Bao1.   

Abstract

Because of the lack of effective alkylating reagents, alkyl etherification of olefins with general alkyl groups has not been previously reported. In this work, a variety of alkyl diacyl peroxides and peresters generated from aliphatic acids have been found to enable the first iron-catalyzed alkyl etherification of olefins with general alkyl groups. Primary, secondary and tertiary aliphatic acids are suitable for this reaction, delivering products with yields up to 97 %. Primary and secondary alcohols react well, affording products in up to 91 % yield.
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  aliphatic acids; alkyl etherification; diacyl peroxide; iron; perester

Year:  2017        PMID: 28230308     DOI: 10.1002/anie.201612365

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  11 in total

1.  Organocatalytic Olefin Aziridination via Iminium-Catalyzed Nitrene Transfer: Scope, Limitations, and Mechanistic Insight.

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3.  Copper-catalyzed formylation of alkenyl C-H bonds using BrCHCl2 as a stoichiometric formylating reagent.

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Journal:  Chem Sci       Date:  2018-02-14       Impact factor: 9.825

4.  Copper-catalyzed methylative difunctionalization of alkenes.

Authors:  Xu Bao; Takayuki Yokoe; Tu M Ha; Qian Wang; Jieping Zhu
Journal:  Nat Commun       Date:  2018-09-13       Impact factor: 14.919

5.  HOTf-Catalyzed Alkyl-Heck-type Reaction.

Authors:  Huan Zhou; Liang Ge; Jinshuai Song; Wujun Jian; Yajun Li; Chunsen Li; Hongli Bao
Journal:  iScience       Date:  2018-05-01

6.  Iron-catalyzed carboazidation of alkenes and alkynes.

Authors:  Haigen Xiong; Nagarajan Ramkumar; Mong-Feng Chiou; Wujun Jian; Yajun Li; Ji-Hu Su; Xinhao Zhang; Hongli Bao
Journal:  Nat Commun       Date:  2019-01-10       Impact factor: 14.919

7.  Saturated oxygen and nitrogen heterocycles via oxidative coupling of alkyltrifluoroborates with alkenols, alkenoic acids and protected alkenylamines.

Authors:  Jonathan M Shikora; Chanchamnan Um; Zainab M Khoder; Sherry R Chemler
Journal:  Chem Sci       Date:  2019-08-19       Impact factor: 9.825

Review 8.  Difunctionalization of Alkenes and Alkynes via Intermolecular Radical and Nucleophilic Additions.

Authors:  Hongjun Yao; Wenfei Hu; Wei Zhang
Journal:  Molecules       Date:  2020-12-28       Impact factor: 4.411

9.  Facile Electrochemical Intramolecular Amination of Urea-Tethered Terminal Alkenes for the Synthesis of Cyclic Ureas.

Authors:  Nisar Ahmed; Saira Khatoon
Journal:  ChemistryOpen       Date:  2018-07-09       Impact factor: 2.911

10.  Revealing the Iron-Catalyzed β-Methyl Scission of tert-Butoxyl Radicals via the Mechanistic Studies of Carboazidation of Alkenes.

Authors:  Mong-Feng Chiou; Haigen Xiong; Yajun Li; Hongli Bao; Xinhao Zhang
Journal:  Molecules       Date:  2020-03-09       Impact factor: 4.411

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