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A direct route to six and seven membered lactones via γ-C(sp(3))–H activation: a simple protocol to build molecular complexity

Lactones comprise a class of valuable compounds having biological as well as industrial importance. Development of a methodology to synthesize such molecules directly from readily available materials such as aliphatic carboxylic acid is highly desirable. Herein, we have reported synthesis of δ-lacto...

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Autores principales: Das, Jayabrata, Dolui, Pravas, Ali, Wajid, Biswas, Jyoti Prasad, Chandrashekar, Hediyala B., Prakash, Gaurav, Maiti, Debabrata
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8162128/
https://www.ncbi.nlm.nih.gov/pubmed/34094235
http://dx.doi.org/10.1039/d0sc03144e
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author Das, Jayabrata
Dolui, Pravas
Ali, Wajid
Biswas, Jyoti Prasad
Chandrashekar, Hediyala B.
Prakash, Gaurav
Maiti, Debabrata
author_facet Das, Jayabrata
Dolui, Pravas
Ali, Wajid
Biswas, Jyoti Prasad
Chandrashekar, Hediyala B.
Prakash, Gaurav
Maiti, Debabrata
author_sort Das, Jayabrata
collection PubMed
description Lactones comprise a class of valuable compounds having biological as well as industrial importance. Development of a methodology to synthesize such molecules directly from readily available materials such as aliphatic carboxylic acid is highly desirable. Herein, we have reported synthesis of δ-lactones and ε-lactones via selective γ-C(sp(3))–H activation. The γ-C–H bond containing aliphatic carboxylic acids provide six or seven membered lactones depending on the olefin partner in the presence of a palladium catalyst. A mechanistic investigation suggests that C–H activation is the rate-determining step. Further transformations of the lactones have been carried out to showcase the applicability of the present strategy.
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spelling pubmed-81621282021-06-04 A direct route to six and seven membered lactones via γ-C(sp(3))–H activation: a simple protocol to build molecular complexity Das, Jayabrata Dolui, Pravas Ali, Wajid Biswas, Jyoti Prasad Chandrashekar, Hediyala B. Prakash, Gaurav Maiti, Debabrata Chem Sci Chemistry Lactones comprise a class of valuable compounds having biological as well as industrial importance. Development of a methodology to synthesize such molecules directly from readily available materials such as aliphatic carboxylic acid is highly desirable. Herein, we have reported synthesis of δ-lactones and ε-lactones via selective γ-C(sp(3))–H activation. The γ-C–H bond containing aliphatic carboxylic acids provide six or seven membered lactones depending on the olefin partner in the presence of a palladium catalyst. A mechanistic investigation suggests that C–H activation is the rate-determining step. Further transformations of the lactones have been carried out to showcase the applicability of the present strategy. The Royal Society of Chemistry 2020-08-19 /pmc/articles/PMC8162128/ /pubmed/34094235 http://dx.doi.org/10.1039/d0sc03144e Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Das, Jayabrata
Dolui, Pravas
Ali, Wajid
Biswas, Jyoti Prasad
Chandrashekar, Hediyala B.
Prakash, Gaurav
Maiti, Debabrata
A direct route to six and seven membered lactones via γ-C(sp(3))–H activation: a simple protocol to build molecular complexity
title A direct route to six and seven membered lactones via γ-C(sp(3))–H activation: a simple protocol to build molecular complexity
title_full A direct route to six and seven membered lactones via γ-C(sp(3))–H activation: a simple protocol to build molecular complexity
title_fullStr A direct route to six and seven membered lactones via γ-C(sp(3))–H activation: a simple protocol to build molecular complexity
title_full_unstemmed A direct route to six and seven membered lactones via γ-C(sp(3))–H activation: a simple protocol to build molecular complexity
title_short A direct route to six and seven membered lactones via γ-C(sp(3))–H activation: a simple protocol to build molecular complexity
title_sort direct route to six and seven membered lactones via γ-c(sp(3))–h activation: a simple protocol to build molecular complexity
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8162128/
https://www.ncbi.nlm.nih.gov/pubmed/34094235
http://dx.doi.org/10.1039/d0sc03144e
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