Literature DB >> 29235224

Cobalt(II)-based Metalloradical Activation of 2-(Diazomethyl)pyridines for Radical Transannulation and Cyclopropanation.

Satyajit Roy1, Sandip Kumar Das1, Buddhadeb Chattopadhyay1.   

Abstract

A new catalytic method for the denitrogenative transannulation/cyclopropanation of in-situ-generated 2-(diazomethyl)pyridines is described using a cobalt-catalyzed radical-activation mechanism. The method takes advantage of the inherent properties of a CoIII -carbene radical intermediate and is the first report of denitrogenative transannulation/cyclopropanation by a radical-activation mechanism, which is supported by various control experiments. The synthetic benefits of the metalloradical approach are showcased with a short total synthesis of (±)-monomorine.
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  carbenes; cyclopropanation; homogeneous catalysis; nitrogen heterocycles; transannulation

Year:  2018        PMID： 29235224     DOI： 10.1002/anie.201711209

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


  16 in total

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Authors:  Jing Ke; Wan-Chen Cindy Lee; Xiaoxu Wang; Yong Wang; Xin Wen; X Peter Zhang
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Authors:  Yong Wang; Xin Wen; Xin Cui; X Peter Zhang
Journal:  J Am Chem Soc       Date:  2018-04-03       Impact factor: 15.419

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Authors:  Chaoqun Li; Kai Lang; Hongjian Lu; Yang Hu; Xin Cui; Lukasz Wojtas; X Peter Zhang
Journal:  Angew Chem Int Ed Engl       Date:  2018-11-16       Impact factor: 15.336

4.  Enantioconvergent Amination of Racemic Tertiary C-H Bonds.

Authors:  Kai Lang; Chaoqun Li; Isaac Kim; X Peter Zhang
Journal:  J Am Chem Soc       Date:  2020-11-29       Impact factor: 15.419

5.  Enantioselective Radical Construction of 5-Membered Cyclic Sulfonamides by Metalloradical C-H Amination.

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Journal:  J Am Chem Soc       Date:  2019-11-01       Impact factor: 15.419

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7.  Revisiting the Electronic Structure of Cobalt Porphyrin Nitrene and Carbene Radicals with NEVPT2-CASSCF Calculations: Doublet versus Quartet Ground States.

Authors:  Nicolaas P van Leest; Bas de Bruin
Journal:  Inorg Chem       Date:  2021-06-05       Impact factor: 5.165

8.  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.  Asymmetric Radical Process for General Synthesis of Chiral Heteroaryl Cyclopropanes.

Authors:  Xiaoxu Wang; Jing Ke; Yiling Zhu; Arghya Deb; Yijie Xu; X Peter Zhang
Journal:  J Am Chem Soc       Date:  2021-07-20       Impact factor: 16.383

10.  Controlling Enantioselectivity and Diastereoselectivity in Radical Cascade Cyclization for Construction of Bicyclic Structures.

Authors:  Congzhe Zhang; Duo-Sheng Wang; Wan-Chen Cindy Lee; Alexander M McKillop; X Peter Zhang
Journal:  J Am Chem Soc       Date:  2021-07-14       Impact factor: 16.383
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