Chemoselective Ullmann Reaction of α-Trisubstituted Thioamides: Synthesis of Novel 2-Iminobenzothiolanes

[Image: see text] New classes of unexplored benzo[b]thiolanes are synthesized from trisubstituted thioamides through copper-catalyzed intramolecular S-arylation of thioamides for the first time. This method provides good to excellent yields with fully controlled chemoselectivity. Unusually, iminoben...

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Autores principales: Bhattacharya, Anwesha, Thirupathi, Annaram, Natarajan, Pradeep, Peruncheralathan, Saravanan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8375098/
https://www.ncbi.nlm.nih.gov/pubmed/34423225
http://dx.doi.org/10.1021/acsomega.1c03410
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author Bhattacharya, Anwesha
Thirupathi, Annaram
Natarajan, Pradeep
Peruncheralathan, Saravanan
author_facet Bhattacharya, Anwesha
Thirupathi, Annaram
Natarajan, Pradeep
Peruncheralathan, Saravanan
author_sort Bhattacharya, Anwesha
collection PubMed
description [Image: see text] New classes of unexplored benzo[b]thiolanes are synthesized from trisubstituted thioamides through copper-catalyzed intramolecular S-arylation of thioamides for the first time. This method provides good to excellent yields with fully controlled chemoselectivity. Unusually, iminobenzo[b]thiolanes are very stable under mild acidic conditions. A plausible mechanism is proposed for the chemoselective S-arylation process.
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spelling pubmed-83750982021-08-20 Chemoselective Ullmann Reaction of α-Trisubstituted Thioamides: Synthesis of Novel 2-Iminobenzothiolanes Bhattacharya, Anwesha Thirupathi, Annaram Natarajan, Pradeep Peruncheralathan, Saravanan ACS Omega [Image: see text] New classes of unexplored benzo[b]thiolanes are synthesized from trisubstituted thioamides through copper-catalyzed intramolecular S-arylation of thioamides for the first time. This method provides good to excellent yields with fully controlled chemoselectivity. Unusually, iminobenzo[b]thiolanes are very stable under mild acidic conditions. A plausible mechanism is proposed for the chemoselective S-arylation process. American Chemical Society 2021-08-04 /pmc/articles/PMC8375098/ /pubmed/34423225 http://dx.doi.org/10.1021/acsomega.1c03410 Text en © 2021 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Bhattacharya, Anwesha
Thirupathi, Annaram
Natarajan, Pradeep
Peruncheralathan, Saravanan
Chemoselective Ullmann Reaction of α-Trisubstituted Thioamides: Synthesis of Novel 2-Iminobenzothiolanes
title Chemoselective Ullmann Reaction of α-Trisubstituted Thioamides: Synthesis of Novel 2-Iminobenzothiolanes
title_full Chemoselective Ullmann Reaction of α-Trisubstituted Thioamides: Synthesis of Novel 2-Iminobenzothiolanes
title_fullStr Chemoselective Ullmann Reaction of α-Trisubstituted Thioamides: Synthesis of Novel 2-Iminobenzothiolanes
title_full_unstemmed Chemoselective Ullmann Reaction of α-Trisubstituted Thioamides: Synthesis of Novel 2-Iminobenzothiolanes
title_short Chemoselective Ullmann Reaction of α-Trisubstituted Thioamides: Synthesis of Novel 2-Iminobenzothiolanes
title_sort chemoselective ullmann reaction of α-trisubstituted thioamides: synthesis of novel 2-iminobenzothiolanes
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8375098/
https://www.ncbi.nlm.nih.gov/pubmed/34423225
http://dx.doi.org/10.1021/acsomega.1c03410
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