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Ag(2)O nanoparticle-catalyzed substrate-controlled regioselectivities: direct access to 3-ylidenephthalides and isocoumarins

Herein, we disclose the first example of an efficient, silver oxide nanoparticle-catalyzed, direct regioselective synthesis of 3-ylidenephthalides 11–16 and isocoumarins 17–20via sonogashira type coupling followed by substrate-controlled 5-exo-dig or 6-endo-dig cyclization reaction, respectively. Th...

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Autores principales: Chaudhary, Sandeep, Shyamlal, Bharti Rajesh K., Yadav, Lalit, Tiwari, Mohit K., Kumar, Krishan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9081558/
https://www.ncbi.nlm.nih.gov/pubmed/35540153
http://dx.doi.org/10.1039/c8ra03926g
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author Chaudhary, Sandeep
Shyamlal, Bharti Rajesh K.
Yadav, Lalit
Tiwari, Mohit K.
Kumar, Krishan
author_facet Chaudhary, Sandeep
Shyamlal, Bharti Rajesh K.
Yadav, Lalit
Tiwari, Mohit K.
Kumar, Krishan
author_sort Chaudhary, Sandeep
collection PubMed
description Herein, we disclose the first example of an efficient, silver oxide nanoparticle-catalyzed, direct regioselective synthesis of 3-ylidenephthalides 11–16 and isocoumarins 17–20via sonogashira type coupling followed by substrate-controlled 5-exo-dig or 6-endo-dig cyclization reaction, respectively. This one pot coupling involves reaction of substituted 2-halobenzoic acid with meta/para-substituted and ortho-substituted terminal alkynes, which proceeded in a regioselective manner resulting in the formation of 3-ylidenephthalides or isocoumarins, respectively, in excellent yields (up to 95%) with complete Z-selectivity. This protocol features relatively broad substrate scope, mild conditions, operational simplicity, and is favourable with aromatic/alicyclic terminal alkynes. The competition experiments and gram-scale synthesis further highlight the importance and versatility of the methodology. The proposed mechanistic pathways illustrate that the regioselectivity is substantially being controlled by the substituent(s) present on the acetylenic phenyl ring.
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spelling pubmed-90815582022-05-09 Ag(2)O nanoparticle-catalyzed substrate-controlled regioselectivities: direct access to 3-ylidenephthalides and isocoumarins Chaudhary, Sandeep Shyamlal, Bharti Rajesh K. Yadav, Lalit Tiwari, Mohit K. Kumar, Krishan RSC Adv Chemistry Herein, we disclose the first example of an efficient, silver oxide nanoparticle-catalyzed, direct regioselective synthesis of 3-ylidenephthalides 11–16 and isocoumarins 17–20via sonogashira type coupling followed by substrate-controlled 5-exo-dig or 6-endo-dig cyclization reaction, respectively. This one pot coupling involves reaction of substituted 2-halobenzoic acid with meta/para-substituted and ortho-substituted terminal alkynes, which proceeded in a regioselective manner resulting in the formation of 3-ylidenephthalides or isocoumarins, respectively, in excellent yields (up to 95%) with complete Z-selectivity. This protocol features relatively broad substrate scope, mild conditions, operational simplicity, and is favourable with aromatic/alicyclic terminal alkynes. The competition experiments and gram-scale synthesis further highlight the importance and versatility of the methodology. The proposed mechanistic pathways illustrate that the regioselectivity is substantially being controlled by the substituent(s) present on the acetylenic phenyl ring. The Royal Society of Chemistry 2018-06-26 /pmc/articles/PMC9081558/ /pubmed/35540153 http://dx.doi.org/10.1039/c8ra03926g Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Chaudhary, Sandeep
Shyamlal, Bharti Rajesh K.
Yadav, Lalit
Tiwari, Mohit K.
Kumar, Krishan
Ag(2)O nanoparticle-catalyzed substrate-controlled regioselectivities: direct access to 3-ylidenephthalides and isocoumarins
title Ag(2)O nanoparticle-catalyzed substrate-controlled regioselectivities: direct access to 3-ylidenephthalides and isocoumarins
title_full Ag(2)O nanoparticle-catalyzed substrate-controlled regioselectivities: direct access to 3-ylidenephthalides and isocoumarins
title_fullStr Ag(2)O nanoparticle-catalyzed substrate-controlled regioselectivities: direct access to 3-ylidenephthalides and isocoumarins
title_full_unstemmed Ag(2)O nanoparticle-catalyzed substrate-controlled regioselectivities: direct access to 3-ylidenephthalides and isocoumarins
title_short Ag(2)O nanoparticle-catalyzed substrate-controlled regioselectivities: direct access to 3-ylidenephthalides and isocoumarins
title_sort ag(2)o nanoparticle-catalyzed substrate-controlled regioselectivities: direct access to 3-ylidenephthalides and isocoumarins
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9081558/
https://www.ncbi.nlm.nih.gov/pubmed/35540153
http://dx.doi.org/10.1039/c8ra03926g
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