NIS/HFIP‐Mediated Synthesis of Indene‐Based β‐Iodoalkenyl Sulfides from Propargylic Sulfides

NIS/HFIP‐Mediated Synthesis of Indene‐Based β‐Iodoalkenyl Sulfides from Propargylic Sulfides

A tandem 1,3‐sulfur migration followed by iodocyclization reaction of propargylic sulfides in the presence of NIS in HFIP has been developed to synthesize indene‐based β‐iodoalkenyl sulfides. The choice of the reaction media is crucial to promote the reaction. The proposed mechanism involving the in...

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Veröffentlicht in:Advanced synthesis & catalysis 2022-09, Vol.364 (17), p.2932-2938
Hauptverfasser: Velasco, Noelia, Martínez‐Núñez, Clara, Fernández‐Rodríguez, Manuel A., Sanz, Roberto, Suárez‐Pantiga, Samuel
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Sprache:eng
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alkenes
alkynes
halogens
Indene
Sulfides
Sulfur
synthetic methods
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container_end_page 2938
container_issue 17
container_start_page 2932
container_title Advanced synthesis & catalysis
container_volume 364
creator Velasco, Noelia
Martínez‐Núñez, Clara
Fernández‐Rodríguez, Manuel A.
Sanz, Roberto
Suárez‐Pantiga, Samuel
description A tandem 1,3‐sulfur migration followed by iodocyclization reaction of propargylic sulfides in the presence of NIS in HFIP has been developed to synthesize indene‐based β‐iodoalkenyl sulfides. The choice of the reaction media is crucial to promote the reaction. The proposed mechanism involving the initial NIS activation by HFIP and favoring the sulfur migration of the starting propargylic thioether via cationic intermediates is experimentally supported. In addition, the suitability of selected indene‐based β‐iodoalkenyl sulfides as building blocks for subsequent C−C bond‐forming reactions has been demonstrated.
doi_str_mv 10.1002/adsc.202200613
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subjects alkenes
alkynes
halogens
Indene
Sulfides
Sulfur
synthetic methods
title NIS/HFIP‐Mediated Synthesis of Indene‐Based β‐Iodoalkenyl Sulfides from Propargylic Sulfides
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