Cargando…

Assessing Methodologies to Synthesize α‐Sulfenylated Carbonyl Compounds by Green Chemistry Metrics

α‐Sulfenylated carbonyl compounds are important both as active pharmaceutical ingredients and as intermediates in organic synthesis. Owing to their relevance in synthetic organic chemistry, this Minireview focuses on assessing the most relevant synthetic procedures based on green chemistry metrics....

Descripción completa

Detalles Bibliográficos
Autores principales: Margalef, Jèssica, Samec, Joseph S. M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7894555/
https://www.ncbi.nlm.nih.gov/pubmed/33180999
http://dx.doi.org/10.1002/cssc.202002409
_version_ 1783653276227469312
author Margalef, Jèssica
Samec, Joseph S. M.
author_facet Margalef, Jèssica
Samec, Joseph S. M.
author_sort Margalef, Jèssica
collection PubMed
description α‐Sulfenylated carbonyl compounds are important both as active pharmaceutical ingredients and as intermediates in organic synthesis. Owing to their relevance in synthetic organic chemistry, this Minireview focuses on assessing the most relevant synthetic procedures based on green chemistry metrics. The Minireview starts with the traditional routes and then focuses on more recently developed methodologies. These routes include sulfenylating reagents using organocatalysis, cross‐dehydrogenative couplings using in situ halogenations to prevent reactive intermediates in high concentrations, oxidative couplings using terminal oxidants such as DDQ or TEMPO, and redox‐neutral couplings using transition metal catalysis. These methodologies have been evaluated on the basis of atom economy, E factor, and the safety and toxicity of the transformations and the solvents used. Besides using green metrics to evaluate these novel methodologies, the synthetic utility is also assessed with regard to the availability of starting materials and the generality of the reactions. This Minireview aims to inspire researchers to apply green assessments to other methodologies and also for them to take measures to increase the greenness of their developed transformations.
format Online
Article
Text
id pubmed-7894555
institution National Center for Biotechnology Information
language English
publishDate 2020
publisher John Wiley and Sons Inc.
record_format MEDLINE/PubMed
spelling pubmed-78945552021-03-02 Assessing Methodologies to Synthesize α‐Sulfenylated Carbonyl Compounds by Green Chemistry Metrics Margalef, Jèssica Samec, Joseph S. M. ChemSusChem Minireviews α‐Sulfenylated carbonyl compounds are important both as active pharmaceutical ingredients and as intermediates in organic synthesis. Owing to their relevance in synthetic organic chemistry, this Minireview focuses on assessing the most relevant synthetic procedures based on green chemistry metrics. The Minireview starts with the traditional routes and then focuses on more recently developed methodologies. These routes include sulfenylating reagents using organocatalysis, cross‐dehydrogenative couplings using in situ halogenations to prevent reactive intermediates in high concentrations, oxidative couplings using terminal oxidants such as DDQ or TEMPO, and redox‐neutral couplings using transition metal catalysis. These methodologies have been evaluated on the basis of atom economy, E factor, and the safety and toxicity of the transformations and the solvents used. Besides using green metrics to evaluate these novel methodologies, the synthetic utility is also assessed with regard to the availability of starting materials and the generality of the reactions. This Minireview aims to inspire researchers to apply green assessments to other methodologies and also for them to take measures to increase the greenness of their developed transformations. John Wiley and Sons Inc. 2020-11-23 2021-02-05 /pmc/articles/PMC7894555/ /pubmed/33180999 http://dx.doi.org/10.1002/cssc.202002409 Text en © 2020 The Authors. ChemSusChem published by Wiley-VCH GmbH This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Minireviews
Margalef, Jèssica
Samec, Joseph S. M.
Assessing Methodologies to Synthesize α‐Sulfenylated Carbonyl Compounds by Green Chemistry Metrics
title Assessing Methodologies to Synthesize α‐Sulfenylated Carbonyl Compounds by Green Chemistry Metrics
title_full Assessing Methodologies to Synthesize α‐Sulfenylated Carbonyl Compounds by Green Chemistry Metrics
title_fullStr Assessing Methodologies to Synthesize α‐Sulfenylated Carbonyl Compounds by Green Chemistry Metrics
title_full_unstemmed Assessing Methodologies to Synthesize α‐Sulfenylated Carbonyl Compounds by Green Chemistry Metrics
title_short Assessing Methodologies to Synthesize α‐Sulfenylated Carbonyl Compounds by Green Chemistry Metrics
title_sort assessing methodologies to synthesize α‐sulfenylated carbonyl compounds by green chemistry metrics
topic Minireviews
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7894555/
https://www.ncbi.nlm.nih.gov/pubmed/33180999
http://dx.doi.org/10.1002/cssc.202002409
work_keys_str_mv AT margalefjessica assessingmethodologiestosynthesizeasulfenylatedcarbonylcompoundsbygreenchemistrymetrics
AT samecjosephsm assessingmethodologiestosynthesizeasulfenylatedcarbonylcompoundsbygreenchemistrymetrics