Literature DB >> 30277643

Borocyclopropanation of Styrenes Mediated by UV-light Under Continuous Flow Conditions.

Morgane Sayes1, Guillaume Benoit1, André B Charette1.   

Abstract

Herein, we report a user-friendly and metal-free UV-A light mediated borocyclopropanation of styrenes using continuous flow technology. A broad range of styrene derivatives can be cyclopropanated in good yields within 1 h residence time to produce highly valuable cyclopropylboronate esters with modest to good diastereoselectivities. The reaction is also applicable to α-substituted styrenes. Mechanistic studies support a photoredox process during which xanthone, a well-known organic photosensitizer, can easily reach a photoexcited state that is available for both an oxidative and a reductive quenching.
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  UV-light; borocyclopropanes; continuous flow; photochemistry; radicals

Year:  2018        PMID: 30277643     DOI: 10.1002/anie.201807347

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


  4 in total

1.  Photocatalyzed Diastereoselective Isomerization of Cinnamyl Chlorides to Cyclopropanes.

Authors:  Bin Xu; Ludovic Troian-Gautier; Ryan Dykstra; Robert T Martin; Osvaldo Gutierrez; Uttam K Tambar
Journal:  J Am Chem Soc       Date:  2020-03-19       Impact factor: 15.419

Review 2.  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 3.  The Impact of Boron Hybridisation on Photocatalytic Processes.

Authors:  Alessandro Marotta; Callum E Adams; John J Molloy
Journal:  Angew Chem Int Ed Engl       Date:  2022-08-10       Impact factor: 16.823

4.  A transition-metal-free & diazo-free styrene cyclopropanation.

Authors:  Ana G Herraiz; Marcos G Suero
Journal:  Chem Sci       Date:  2019-08-28       Impact factor: 9.825

  4 in total

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