Radical coupling of β-ketoesters and amides promoted by Brønsted/Lewis acids

Recent advances in photocatalysis have enabled radical methods with complementary chemoselectivity to established two electron bond forming approaches. While this radical strategy has previously been limited to substrates with favorable redox potentials, Brønsted/Lewis acid activation has emerged as...

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Main Authors:	Joshua L. Zhu, Stephen W. Laws, Michael J. Rourke, Karl A. Scheidt
Format:	Article
Language:	English
Published:	KeAi Communications Co. Ltd. 2020-06-01
Series:	Green Synthesis and Catalysis
Subjects:	Photochemistry Lewis acid Catalysis Alkylation Radicals
Online Access:	http://www.sciencedirect.com/science/article/pii/S2666554920300107

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spelling	doaj-7df9b633a72f48a6bd8cd02c009e14e12021-10-05T04:21:27ZengKeAi Communications Co. Ltd.Green Synthesis and Catalysis2666-55492020-06-01117074Radical coupling of β-ketoesters and amides promoted by Brønsted/Lewis acidsJoshua L. Zhu0Stephen W. Laws1Michael J. Rourke2Karl A. Scheidt3Department of Chemistry, Center for Molecular Innovation and Drug Discovery, Northwestern University, Evanston, IL 60208, United StatesDepartment of Chemistry, Center for Molecular Innovation and Drug Discovery, Northwestern University, Evanston, IL 60208, United StatesDepartment of Chemistry, Center for Molecular Innovation and Drug Discovery, Northwestern University, Evanston, IL 60208, United StatesCorresponding author.; Department of Chemistry, Center for Molecular Innovation and Drug Discovery, Northwestern University, Evanston, IL 60208, United StatesRecent advances in photocatalysis have enabled radical methods with complementary chemoselectivity to established two electron bond forming approaches. While this radical strategy has previously been limited to substrates with favorable redox potentials, Brønsted/Lewis acid activation has emerged as a means of facilitating otherwise difficult reductions. We report herein our investigations into the Lewis acid-promoted redox activation of β-ketocarbonyls in a model photocatalytic radical alkylation reaction. Rapid evaluation of substrates and reactions conditions was achieved by high throughput experimentation using 96-well plate photoreactors.http://www.sciencedirect.com/science/article/pii/S2666554920300107PhotochemistryLewis acidCatalysisAlkylationRadicals
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Joshua L. Zhu Stephen W. Laws Michael J. Rourke Karl A. Scheidt
spellingShingle	Joshua L. Zhu Stephen W. Laws Michael J. Rourke Karl A. Scheidt Radical coupling of β-ketoesters and amides promoted by Brønsted/Lewis acids Green Synthesis and Catalysis Photochemistry Lewis acid Catalysis Alkylation Radicals
author_facet	Joshua L. Zhu Stephen W. Laws Michael J. Rourke Karl A. Scheidt
author_sort	Joshua L. Zhu
title	Radical coupling of β-ketoesters and amides promoted by Brønsted/Lewis acids
title_short	Radical coupling of β-ketoesters and amides promoted by Brønsted/Lewis acids
title_full	Radical coupling of β-ketoesters and amides promoted by Brønsted/Lewis acids
title_fullStr	Radical coupling of β-ketoesters and amides promoted by Brønsted/Lewis acids
title_full_unstemmed	Radical coupling of β-ketoesters and amides promoted by Brønsted/Lewis acids
title_sort	radical coupling of β-ketoesters and amides promoted by brønsted/lewis acids
publisher	KeAi Communications Co. Ltd.
series	Green Synthesis and Catalysis
issn	2666-5549
publishDate	2020-06-01
description	Recent advances in photocatalysis have enabled radical methods with complementary chemoselectivity to established two electron bond forming approaches. While this radical strategy has previously been limited to substrates with favorable redox potentials, Brønsted/Lewis acid activation has emerged as a means of facilitating otherwise difficult reductions. We report herein our investigations into the Lewis acid-promoted redox activation of β-ketocarbonyls in a model photocatalytic radical alkylation reaction. Rapid evaluation of substrates and reactions conditions was achieved by high throughput experimentation using 96-well plate photoreactors.
topic	Photochemistry Lewis acid Catalysis Alkylation Radicals
url	http://www.sciencedirect.com/science/article/pii/S2666554920300107
work_keys_str_mv	AT joshualzhu radicalcouplingofbketoestersandamidespromotedbybrønstedlewisacids AT stephenwlaws radicalcouplingofbketoestersandamidespromotedbybrønstedlewisacids AT michaeljrourke radicalcouplingofbketoestersandamidespromotedbybrønstedlewisacids AT karlascheidt radicalcouplingofbketoestersandamidespromotedbybrønstedlewisacids
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Radical coupling of β-ketoesters and amides promoted by Brønsted/Lewis acids

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