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Laha, Joydev K., Gulati, Upma, Schulte, Tim and Breugst, Martin (2022). pH-Controlled Intramolecular Decarboxylative Cyclization ofBiarylacetic Acids: Implication on Umpolung Reactivity of Aroyl Radicals. J. Org. Chem., 87 (10). S. 6638 - 6657. WASHINGTON: AMER CHEMICAL SOC. ISSN 1520-6904

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Abstract

A simple approach for the intramolecular aroylation of electron-rich arenes under mild conditions has beendeveloped. A pH-controlled polarity umpolung strategy can be used to synthesize differentfluorenones, which are importantbuilding blocks for biological applications. Unlike previous acylation reactions involving nucleophilic aroyl radicals, this approachlikely relies on in situ generated electrophilic aroyl radicals. Detailed mechanistic and computational investigations provide detailedinsights into the reaction mechanism and support the hypothesis of a pH-mediated umpolung

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Laha, Joydev K. UNSPECIFIED UNSPECIFIED UNSPECIFIED Gulati, Upma UNSPECIFIED UNSPECIFIED UNSPECIFIED Schulte, Tim UNSPECIFIED UNSPECIFIED UNSPECIFIED Breugst, Martin UNSPECIFIED UNSPECIFIED UNSPECIFIED
URN:	urn:nbn:de:hbz:38-674943
DOI:	10.1021/acs.joc.2c00295
Journal or Publication Title:	J. Org. Chem.
Volume:	87
Number:	10
Page Range:	S. 6638 - 6657
Date:	2022
Publisher:	AMER CHEMICAL SOC
Place of Publication:	WASHINGTON
ISSN:	1520-6904
Language:	English
Faculty:	Unspecified
Divisions:	Unspecified
Subjects:	no entry
Uncontrolled Keywords:	Keywords Language DEHYDROGENATIVE ARYLATION; PHOTOCATALYTIC UMPOLUNG; BENZYLIC OXIDATION; BASIS-SETS; ACYLATION; FLUORENONES; CHEMISTRY; ALDEHYDES; ACTIVATION; COMPLEXES Multiple languages Chemistry, Organic Multiple languages
URI:	http://kups.ub.uni-koeln.de/id/eprint/67494