Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 61, Issue 1, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202113658
Keywords
cyclopropanol; heterocycles; photocatalysis; pyridinium salt; reaction mechanisms
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Funding
- Institute for Basic Science [IBS-R010-A2]
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This study presents a general strategy for site-selective C-H functionalization of heteroarenes, specifically achieving high site selectivity at the C4 position of pyridines through visible-light-induced beta-carbonyl alkylation. The method enables the synthesis of valuable beta-pyridylated (aryl)ketones, aldehydes, and esters with broad functional-group tolerance, serving as an effective tool for late-stage functionalization of complex and medicinally relevant molecules.
The site-selective C-H functionalization of heteroarenes is of considerable importance for streamlining the rapid modification of bioactive molecules. Herein, we report a general strategy for visible-light-induced beta-carbonyl alkylation at the C4 position of pyridines with high site selectivity using various cyclopropanols and N-amidopyridinium salts. In this process, hydrogen-atom transfer between the generated sulfonamidyl radicals and O-H bonds of cyclopropanols generates beta-carbonyl radicals, providing efficient access to synthetically valuable beta-pyridylated (aryl)ketones, aldehydes, and esters with broad functional-group tolerance. In addition, the mild method serves as an effective tool for the site-selective late-stage functionalization of complex and medicinally relevant molecules.
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