Stereodivergent Synthesis of (Z)‑/(E)‑β-Sulfonylacrylamides via Tandem Difunctionalization of Alkynes with Sulfinates and Isocyanides

Stereodivergent Synthesis of (Z)‑/(E)‑β-Sulfonylacrylamides via Tandem Difunctionalization of Alkynes with Sulfinates and Isocyanides

Stereoselective difunctionalizations of the terminal and internal alkynes with various sulfinates and isocyanides have been achieved to prepare (Z)-/(E)-β-sulfonylacrylamides. The (Z)-β-sulfonylacrylamides were generated via a one-pot process that involves the reaction of terminal alkynes with sulfi...

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Veröffentlicht in:Organic letters 2022-10, Vol.24 (41), p.7632-7636
Hauptverfasser: Tripathi, Shashank, Kumar, Monty, Ambule, Mayur D., Saxena, Ankit, Kant, Ruchir, Shukla, Sanjeev K., Srivastava, Ajay Kumar
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Sprache:eng
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Alkynes
Catalysis
Cyanides
Iodine
Palladium
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container_end_page 7636
container_issue 41
container_start_page 7632
container_title Organic letters
container_volume 24
creator Tripathi, Shashank
Kumar, Monty
Ambule, Mayur D.
Saxena, Ankit
Kant, Ruchir
Shukla, Sanjeev K.
Srivastava, Ajay Kumar
description Stereoselective difunctionalizations of the terminal and internal alkynes with various sulfinates and isocyanides have been achieved to prepare (Z)-/(E)-β-sulfonylacrylamides. The (Z)-β-sulfonylacrylamides were generated via a one-pot process that involves the reaction of terminal alkynes with sulfinates and isocyanides in the presence of iodine in sequential manner. The (E)-β-sulfonylacrylamides were prepared in a two-step synthesis via palladium­(II)-catalyzed addition of isocyanide to (E)-β-iodovinylsulfones synthesized from alkynes.
doi_str_mv 10.1021/acs.orglett.2c03092
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source MEDLINE; ACS Publications
subjects Alkynes
Catalysis
Cyanides
Iodine
Palladium
title Stereodivergent Synthesis of (Z)‑/(E)‑β-Sulfonylacrylamides via Tandem Difunctionalization of Alkynes with Sulfinates and Isocyanides
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