Difluoroenoxysilane: Expanding Allenamide Hydrodifluoroalkylation for Diverse Carbon Frameworks

This study presents an effective route to access functionalizable fluorinated enamides characterized by their high regiospecificity around the allenamide. Synthetic applications of the resulting difluorocarbonyl-bearing enamide products were pursued through straightforward synthetic transformations...

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Veröffentlicht in:	Organic letters 2024-07, Vol.26 (27), p.5676-5681
Hauptverfasser:	Sagar, Kadiyala, Srimannarayana, Malempati, Teegala, Raju, Merja, Bhailal C., Pradhan, Tapas R., Park, Jin Kyoon
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Sprache:	eng
Schlagworte:	carbon heterocyclic oxygen compounds Lewis acids regioselectivity
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creator	Sagar, Kadiyala Srimannarayana, Malempati Teegala, Raju Merja, Bhailal C. Pradhan, Tapas R. Park, Jin Kyoon
description	This study presents an effective route to access functionalizable fluorinated enamides characterized by their high regiospecificity around the allenamide. Synthetic applications of the resulting difluorocarbonyl-bearing enamide products were pursued through straightforward synthetic transformations to prepare unknown functionalized valuable halogenated O-heterocycles and C5 skeletons. Experimental mechanistic studies showed that hydrodifluoroalkylation occurs via a hidden Brønsted acid activation, thereby establishing a new electrophilic activation mode for allenamide through a conjugated iminium intermediate.
doi_str_mv	10.1021/acs.orglett.4c01703
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subjects	carbon heterocyclic oxygen compounds Lewis acids regioselectivity
title	Difluoroenoxysilane: Expanding Allenamide Hydrodifluoroalkylation for Diverse Carbon Frameworks
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