Journal article

Transition metal-free, visible light-mediated radical cyclisation of malonyl radicals onto 5-ring heteroaromatics

Abstract:: Annulated heteroaromatics can be accessed through the addition of malonyl radicals onto heterocycles. Current methods are applicable to electron-rich heteroaromatics and reliant on transition metals or toxic tin reagents. Here we report a metal-free, visible light-mediated cyclisation of malonates onto 5-ring heteroaromatics using iodomalonates as key intermediates. The iodomalonates are prepared and photolysed in situ to give the desired annulated products, in yields of 46–94% without the need for external catalysts. The scope of this transformation includes N-alkyl, N-acyl and carbon-tethered malonates adding onto a wide range of 5-membered heteroaromatics.

Publication status:: Published

Peer review status:: Peer reviewed

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APA Style

Hernandez-Llado, P., Garrec, K., Schmitt, D. C., & Burton, J. W. (2022). Transition metal-free, visible light-mediated radical cyclisation of malonyl radicals onto 5-ring heteroaromatics . Advanced Synthesis and Catalysis, 364(10), 1724–1731.

MLA Style

Hernandez-Llado, P., et al. “Transition Metal-Free, Visible Light-Mediated Radical Cyclisation of Malonyl Radicals onto 5-Ring Heteroaromatics .” Advanced Synthesis and Catalysis, vol. 364, no. 10, Wiley, 2022, pp. 1724–31.

Chicago Style

Hernandez-Llado, P, K Garrec, DC Schmitt, and JW Burton. 2022. “Transition Metal-Free, Visible Light-Mediated Radical Cyclisation of Malonyl Radicals onto 5-Ring Heteroaromatics .” Advanced Synthesis and Catalysis 364 (10): 1724–31.
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Files:: Hernandez-Llado_et_al_2022_Transition_Metal-FreeAM.pdf.pdf

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Hernandez-Llado_et_al_2022_Transition_Metal-FreeSM.pdf

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Publisher copy:: 10.1002/adsc.202101451

Authors

+ Hernandez-Llado, P More by this author

Role:: Author

+ Garrec, K More by this author

Role:: Author

+ Schmitt, DC More by this author

Role:: Author

+ Burton, JW More by this author

Institution:: University of Oxford
Division:: MPLS
Department:: Chemistry
Sub department:: Organic Chemistry
Oxford college:: Somerville College
Role:: Author

Publisher:: Wiley
Journal:: Advanced Synthesis and Catalysis More from this journal
Volume:: 364
Issue:: 10
Pages:: 1724-1731
Publication date:: 2022-04-04
Acceptance date:: 2022-03-22
DOI:: 10.1002/adsc.202101451
EISSN:: 1615-4169
ISSN:: 1615-4150

Language:: English
Keywords:: FFR

heterocycles

annulation

synthetic methods

photochemistry

radical reactions
Pubs id:: 1251464
Local pid:: pubs:1251464
Deposit date:: 2022-06-27

Terms of use

Copyright holder:: Wiley
Copyright date:: 2022
Rights statement:: ©2022 Wiley-VCH GmbH
Notes:: This is the accepted manuscript version of the article. The final version is available from Wiley at: 10.1002/adsc.202101451

Licence:: Terms and Conditions of Use for Oxford University Research Archive

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