Cargando…
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...
Autores principales: | , , , , , , |
---|---|
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 |
_version_ | 1783700646443089920 |
---|---|
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. |
format | Online Article Text |
id | pubmed-8162128 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
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 |
work_keys_str_mv | AT dasjayabrata adirectroutetosixandsevenmemberedlactonesviagcsp3hactivationasimpleprotocoltobuildmolecularcomplexity AT doluipravas adirectroutetosixandsevenmemberedlactonesviagcsp3hactivationasimpleprotocoltobuildmolecularcomplexity AT aliwajid adirectroutetosixandsevenmemberedlactonesviagcsp3hactivationasimpleprotocoltobuildmolecularcomplexity AT biswasjyotiprasad adirectroutetosixandsevenmemberedlactonesviagcsp3hactivationasimpleprotocoltobuildmolecularcomplexity AT chandrashekarhediyalab adirectroutetosixandsevenmemberedlactonesviagcsp3hactivationasimpleprotocoltobuildmolecularcomplexity AT prakashgaurav adirectroutetosixandsevenmemberedlactonesviagcsp3hactivationasimpleprotocoltobuildmolecularcomplexity AT maitidebabrata adirectroutetosixandsevenmemberedlactonesviagcsp3hactivationasimpleprotocoltobuildmolecularcomplexity AT dasjayabrata directroutetosixandsevenmemberedlactonesviagcsp3hactivationasimpleprotocoltobuildmolecularcomplexity AT doluipravas directroutetosixandsevenmemberedlactonesviagcsp3hactivationasimpleprotocoltobuildmolecularcomplexity AT aliwajid directroutetosixandsevenmemberedlactonesviagcsp3hactivationasimpleprotocoltobuildmolecularcomplexity AT biswasjyotiprasad directroutetosixandsevenmemberedlactonesviagcsp3hactivationasimpleprotocoltobuildmolecularcomplexity AT chandrashekarhediyalab directroutetosixandsevenmemberedlactonesviagcsp3hactivationasimpleprotocoltobuildmolecularcomplexity AT prakashgaurav directroutetosixandsevenmemberedlactonesviagcsp3hactivationasimpleprotocoltobuildmolecularcomplexity AT maitidebabrata directroutetosixandsevenmemberedlactonesviagcsp3hactivationasimpleprotocoltobuildmolecularcomplexity |