Literature DB >> 30480350

Blue-Light-Induced Carbene-Transfer Reactions of Diazoalkanes.

Renè Hommelsheim1, Yujing Guo1, Zhen Yang1, Claire Empel1, Rene M Koenigs1.   

Abstract

Carbenes are very important reactive intermediates to access a variety of complex molecules and are applied widely in organic synthesis and drug discovery. Typically, their chemistry is accessed by the use of transition metal catalysts. Herein, we describe the application of low-energy blue light for the photochemical generation of carbenes from donor-acceptor diazoalkanes. This catalyst-free and operationally simple approach enables highly efficient cyclopropenation reactions with alkynes and the rearrangement of sulfides under mild reaction conditions, which can be utilized for both batch and continuous-flow processes.
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  continuous-flow; cyclopropenation; diazoalkanes; photochemistry; rearrangement

Year:  2018        PMID: 30480350     DOI: 10.1002/anie.201811991

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


  16 in total

Review 1.  Technological Innovations in Photochemistry for Organic Synthesis: Flow Chemistry, High-Throughput Experimentation, Scale-up, and Photoelectrochemistry.

Authors:  Laura Buglioni; Fabian Raymenants; Aidan Slattery; Stefan D A Zondag; Timothy Noël
Journal:  Chem Rev       Date:  2021-08-10       Impact factor: 60.622

Review 2.  Continuous Flow Technology as an Enabler for Innovative Transformations Exploiting Carbenes, Nitrenes, and Benzynes.

Authors:  Kian Donnelly; Marcus Baumann
Journal:  J Org Chem       Date:  2022-06-14       Impact factor: 4.198

3.  Rhodium-catalyzed cascade reactions of triazoles with organoselenium compounds - a combined experimental and mechanistic study.

Authors:  Fang Li; Chao Pei; Rene M Koenigs
Journal:  Chem Sci       Date:  2021-03-24       Impact factor: 9.825

4.  Photochemical ring expansion reactions: synthesis of tetrahydrofuran derivatives and mechanism studies.

Authors:  Sripati Jana; Zhen Yang; Chao Pei; Xinfang Xu; Rene M Koenigs
Journal:  Chem Sci       Date:  2019-09-06       Impact factor: 9.825

5.  Light-induced metal-free transformations of unactivated pyridotriazoles.

Authors:  Ziyan Zhang; Dongari Yadagiri; Vladimir Gevorgyan
Journal:  Chem Sci       Date:  2019-07-25       Impact factor: 9.825

6.  Catalytic Synthesis of Trifluoromethyl Cyclopropenes and Oligo-Cyclopropenes.

Authors:  Uyen P N Tran; Renè Hommelsheim; Zhen Yang; Claire Empel; Katharina J Hock; Thanh V Nguyen; René M Koenigs
Journal:  Chemistry       Date:  2020-01-20       Impact factor: 5.236

7.  Desaturation via Redox-Neutral Hydrogen Transfer Process: Synthesis of 2-Allyl Anilines, Mechanism and Applications.

Authors:  Yang Zheng; Ping Dai; Dafang Gao; Kemiao Hong; Luyao Kou; Shanliang Dong; Jundie Hu; Lihua Qiu; Wenhao Hu; Xiaoguang Bao; Xinfang Xu
Journal:  iScience       Date:  2020-05-15

8.  Synthesis of gem-Difluoro Olefins through C-H Functionalization and β-fluoride Elimination Reactions.

Authors:  Zhen Yang; Mieke Möller; Rene M Koenigs
Journal:  Angew Chem Int Ed Engl       Date:  2020-02-21       Impact factor: 15.336

9.  Stoichiometric Photochemical Carbene Transfer by Bamford-Stevens Reaction.

Authors:  Sripati Jana; Fang Li; Claire Empel; Dennis Verspeek; Polina Aseeva; Rene M Koenigs
Journal:  Chemistry       Date:  2020-02-21       Impact factor: 5.236

10.  Visible Light Induced Metal-Free Carbene N-Carbazolation.

Authors:  Claire Empel; Frederic W Patureau; Rene M Koenigs
Journal:  J Org Chem       Date:  2019-08-15       Impact factor: 4.354

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