A copper(ii)-catalyzed annulative formylation of o-alkynylanilines with DMF: a single-step strategy for 3-formyl indoles

In this paper, a copper(ii)-catalyzed reaction of o-alkynylanilines with dimethylformamide (DMF) in the presence of oxygen has been developed for synthesizing multisubstituted 3-formyl indole scaffolds. This one-pot reaction proceeds through a cascade 5-endo-dig cyclization followed by formylation t...

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Autores principales: Ganesan, Balaji, Senadi, Gopal Chandru, Guo, Bing-Chun, Hung, Min-Yuan, Lin, Wei-Yu
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2018
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9092273/
https://www.ncbi.nlm.nih.gov/pubmed/35557929
http://dx.doi.org/10.1039/c8ra09214a
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author Ganesan, Balaji
Senadi, Gopal Chandru
Guo, Bing-Chun
Hung, Min-Yuan
Lin, Wei-Yu
author_facet Ganesan, Balaji
Senadi, Gopal Chandru
Guo, Bing-Chun
Hung, Min-Yuan
Lin, Wei-Yu
author_sort Ganesan, Balaji
collection PubMed
description In this paper, a copper(ii)-catalyzed reaction of o-alkynylanilines with dimethylformamide (DMF) in the presence of oxygen has been developed for synthesizing multisubstituted 3-formyl indole scaffolds. This one-pot reaction proceeds through a cascade 5-endo-dig cyclization followed by formylation to construct 1,2-disubstituted 3-formyl indoles. The key aspects of this synthesis method are the broad substrate scope (with 38 examples), and well tolerating various functional groups. In addition, a detailed mechanism has been proposed, where DMF may serve as a carbon source for the in situ C3 formylation of the obtained indole derivatives.
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spelling pubmed-90922732022-05-11 A copper(ii)-catalyzed annulative formylation of o-alkynylanilines with DMF: a single-step strategy for 3-formyl indoles Ganesan, Balaji Senadi, Gopal Chandru Guo, Bing-Chun Hung, Min-Yuan Lin, Wei-Yu RSC Adv Chemistry In this paper, a copper(ii)-catalyzed reaction of o-alkynylanilines with dimethylformamide (DMF) in the presence of oxygen has been developed for synthesizing multisubstituted 3-formyl indole scaffolds. This one-pot reaction proceeds through a cascade 5-endo-dig cyclization followed by formylation to construct 1,2-disubstituted 3-formyl indoles. The key aspects of this synthesis method are the broad substrate scope (with 38 examples), and well tolerating various functional groups. In addition, a detailed mechanism has been proposed, where DMF may serve as a carbon source for the in situ C3 formylation of the obtained indole derivatives. The Royal Society of Chemistry 2018-12-07 /pmc/articles/PMC9092273/ /pubmed/35557929 http://dx.doi.org/10.1039/c8ra09214a Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Ganesan, Balaji
Senadi, Gopal Chandru
Guo, Bing-Chun
Hung, Min-Yuan
Lin, Wei-Yu
A copper(ii)-catalyzed annulative formylation of o-alkynylanilines with DMF: a single-step strategy for 3-formyl indoles
title A copper(ii)-catalyzed annulative formylation of o-alkynylanilines with DMF: a single-step strategy for 3-formyl indoles
title_full A copper(ii)-catalyzed annulative formylation of o-alkynylanilines with DMF: a single-step strategy for 3-formyl indoles
title_fullStr A copper(ii)-catalyzed annulative formylation of o-alkynylanilines with DMF: a single-step strategy for 3-formyl indoles
title_full_unstemmed A copper(ii)-catalyzed annulative formylation of o-alkynylanilines with DMF: a single-step strategy for 3-formyl indoles
title_short A copper(ii)-catalyzed annulative formylation of o-alkynylanilines with DMF: a single-step strategy for 3-formyl indoles
title_sort copper(ii)-catalyzed annulative formylation of o-alkynylanilines with dmf: a single-step strategy for 3-formyl indoles
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9092273/
https://www.ncbi.nlm.nih.gov/pubmed/35557929
http://dx.doi.org/10.1039/c8ra09214a
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