Literature DB >> 25425423

Interception of cobalt-based carbene radicals with α-aminoalkyl radicals: a tandem reaction for the construction of β-ester-γ-amino ketones.

Jie Zhang1, Jiewen Jiang, Dongmei Xu, Qiang Luo, Hongxiang Wang, Jijun Chen, Huihuang Li, Yaxiong Wang, Xiaobing Wan.   

Abstract

The interception of cobalt-based carbene radicals with α-aminoalkyl radicals was combined with the Kornblum-DeLaMare reaction and provides β-ester-γ-amino ketones, which are otherwise difficult to obtain in high chemoselectivity. Mechanistically, this transformation is an interplay of cobalt-based carbene radicals, organoradicals, and ionic intermediates and involves the construction of two C-C bonds and one C=O bond in a one-pot process. The reaction also features a wide substrate scope and is highly efficient and insensitive to moisture and air.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  Kornblum-DeLaMare reaction; carbene radicals; cobalt; radical reactions; tandem reactions

Year:  2014        PMID: 25425423     DOI: 10.1002/anie.201408874

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


  9 in total

1.  Asymmetric Radical Bicyclization of Allyl Azidoformates via Cobalt(II)-Based Metalloradical Catalysis.

Authors:  Huiling Jiang; Kai Lang; Hongjian Lu; Lukasz Wojtas; X Peter Zhang
Journal:  J Am Chem Soc       Date:  2017-06-29       Impact factor: 15.419

2.  Asymmetric Radical Cyclopropanation of Alkenes with In Situ-Generated Donor-Substituted Diazo Reagents via Co(II)-Based Metalloradical Catalysis.

Authors:  Yong Wang; Xin Wen; Xin Cui; Lukasz Wojtas; X Peter Zhang
Journal:  J Am Chem Soc       Date:  2017-01-12       Impact factor: 15.419

3.  Metal-free C(sp(3))-H functionalization: oxidative carbo-oxygenation of α-diazo carbonyls via radical dediazotization.

Authors:  Nan-Nan Wang; Wen-Juan Hao; Tian-Shu Zhang; Guigen Li; Ya-Nan Wu; Shu-Jiang Tu; Bo Jiang
Journal:  Chem Commun (Camb)       Date:  2016-03-21       Impact factor: 6.222

4.  Enantioselective Radical Cyclization for Construction of 5-Membered Ring Structures by Metalloradical C-H Alkylation.

Authors:  Yong Wang; Xin Wen; Xin Cui; X Peter Zhang
Journal:  J Am Chem Soc       Date:  2018-04-03       Impact factor: 15.419

5.  Catalytic 1,2-dihydronaphthalene and E-aryl-diene synthesis via CoIII-Carbene radical and o-quinodimethane intermediates.

Authors:  Colet Te Grotenhuis; Braja G Das; Petrus F Kuijpers; Wouter Hageman; Mees Trouwborst; Bas de Bruin
Journal:  Chem Sci       Date:  2017-10-12       Impact factor: 9.825

6.  Catalytic Synthesis of Indolines by Hydrogen Atom Transfer to Cobalt(III)-Carbene Radicals.

Authors:  Alexander S Karns; Monalisa Goswami; Bas de Bruin
Journal:  Chemistry       Date:  2017-12-05       Impact factor: 5.236

7.  A Carbene-Extended ATRA Reaction.

Authors:  Guojiao Wu; Jennifer Börger; Axel Jacobi von Wangelin
Journal:  Angew Chem Int Ed Engl       Date:  2019-10-15       Impact factor: 15.336

8.  Azodioxy compounds as precursors for C-radicals and their application in thermal styrene difunctionalization.

Authors:  Stefanie Plöger; Christian Mück-Lichtenfeld; Constantin G Daniliuc; Armido Studer
Journal:  Chem Sci       Date:  2022-08-05       Impact factor: 9.969

9.  New Catalytic Radical Process Involving 1,4-Hydrogen Atom Abstraction: Asymmetric Construction of Cyclobutanones.

Authors:  Jingjing Xie; Pan Xu; Yiling Zhu; Jingyi Wang; Wan-Chen Cindy Lee; X Peter Zhang
Journal:  J Am Chem Soc       Date:  2021-07-22       Impact factor: 16.383

  9 in total

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