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Chalcogenative spirocyclization of N-aryl propiolamides with diselenides/disulfides promoted by Selectfluor

Chalcogenative spirocyclization of N-aryl propiolamides with diselenides/disulfides promoted by... AbstractA practical and efficient synthetic route to construct a variety of 3-arylselenenyl/3-arylthio spiro[4.5]trienones was developed using Selectfluor reagent as a mild oxidant. This reaction proceeds via a sequence of electrophilic cation addition, spirocyclization and dearomatization, then offers an approach to introduce Se/S-centered cation into the C–C triple bonds. The utility of this protocol were justified by the excellent compatibility of a wide range of functional groups, good yields and scalability under mild reaction conditions. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Zeitschrift für Naturforschung B de Gruyter

Chalcogenative spirocyclization of N-aryl propiolamides with diselenides/disulfides promoted by Selectfluor

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Publisher
de Gruyter
Copyright
© 2021 Walter de Gruyter GmbH, Berlin/Boston
ISSN
0932-0776
eISSN
1865-7117
DOI
10.1515/znb-2021-0154
Publisher site
See Article on Publisher Site

Abstract

AbstractA practical and efficient synthetic route to construct a variety of 3-arylselenenyl/3-arylthio spiro[4.5]trienones was developed using Selectfluor reagent as a mild oxidant. This reaction proceeds via a sequence of electrophilic cation addition, spirocyclization and dearomatization, then offers an approach to introduce Se/S-centered cation into the C–C triple bonds. The utility of this protocol were justified by the excellent compatibility of a wide range of functional groups, good yields and scalability under mild reaction conditions.

Journal

Zeitschrift für Naturforschung Bde Gruyter

Published: Jan 27, 2022

Keywords: cation pathway; chalcogenation; N -aryl propiolamides; Selectfluor; spirocyclization

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