Access to Multifunctionalized Tetrasubstituted Carbon Centers Bearing up to Three Different Heteroatoms via Tandem Geminal Chlorofluorination of 1,2-Dicarbonyl Compounds
The incorporation of noncarbon heteroatoms into organic molecules typically instills characteristic and often valuable functionalities. The copresence of different heteroatoms can further broaden their utility through the synergistic cooperative effects, which may even lead to the discovery of forme...
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Published in | Organic letters Vol. 25; no. 49; pp. 8839 - 8844 |
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Main Authors | , , , |
Format | Journal Article |
Language | English |
Published |
WASHINGTON
American Chemical Society
15.12.2023
Amer Chemical Soc |
Subjects | |
Online Access | Get full text |
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Summary: | The incorporation of noncarbon heteroatoms into organic molecules typically instills characteristic and often valuable functionalities. The copresence of different heteroatoms can further broaden their utility through the synergistic cooperative effects, which may even lead to the discovery of formerly unavailable properties that are not just a simple accumulation of each function. However, despite increasing interest in the controllable installation of heteroatoms, it has been extremely challenging to construct carbon centers having three different heteroatoms in a synthetically useful manner. In this work, our group’s tandem geminal chlorofluorination (Cl, F) strategy was applied to rationally designed heteroatom-bearing 1,2-dicarbonyl substrates, including α-keto thioesters (S), α-keto N-acylindoles (N), and α-keto acylsilane (Si), which resulted in the practical production of doubly or triply heterofunctionalized tetrasubstituted carbon centers with excellent site-selectivity. |
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Bibliography: | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
ISSN: | 1523-7060 1523-7052 |
DOI: | 10.1021/acs.orglett.3c03527 |