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Cobalt catalyzed carbonylation of unactivated C(sp(3))–H bonds

A general efficient regioselective cobalt catalyzed carbonylation of unactivated C(sp(3))–H bonds of aliphatic amides was demonstrated using atmospheric (1–2 atm) carbon monoxide as a C1 source. This straightforward approach provides access to α-spiral succinimide regioselectively in a good yield. C...

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Detalles Bibliográficos
Autores principales: Barsu, Nagaraju, Bolli, Shyam Kumar, Sundararaju, Basker
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2017
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5369400/
https://www.ncbi.nlm.nih.gov/pubmed/28451350
http://dx.doi.org/10.1039/c6sc05026c
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author Barsu, Nagaraju
Bolli, Shyam Kumar
Sundararaju, Basker
author_facet Barsu, Nagaraju
Bolli, Shyam Kumar
Sundararaju, Basker
author_sort Barsu, Nagaraju
collection PubMed
description A general efficient regioselective cobalt catalyzed carbonylation of unactivated C(sp(3))–H bonds of aliphatic amides was demonstrated using atmospheric (1–2 atm) carbon monoxide as a C1 source. This straightforward approach provides access to α-spiral succinimide regioselectively in a good yield. Cobalt catalyzed sp(3) C–H bond carbonylation is reported for the first time including the functionalization of (β)-C–H bonds of α-1°, 2°, 3° carbons and even internal (β)-C–H bonds. Our initial mechanistic investigation reveals that the C–H activation step is irreversible and will possibly be the rate determining step.
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spelling pubmed-53694002017-04-27 Cobalt catalyzed carbonylation of unactivated C(sp(3))–H bonds Barsu, Nagaraju Bolli, Shyam Kumar Sundararaju, Basker Chem Sci Chemistry A general efficient regioselective cobalt catalyzed carbonylation of unactivated C(sp(3))–H bonds of aliphatic amides was demonstrated using atmospheric (1–2 atm) carbon monoxide as a C1 source. This straightforward approach provides access to α-spiral succinimide regioselectively in a good yield. Cobalt catalyzed sp(3) C–H bond carbonylation is reported for the first time including the functionalization of (β)-C–H bonds of α-1°, 2°, 3° carbons and even internal (β)-C–H bonds. Our initial mechanistic investigation reveals that the C–H activation step is irreversible and will possibly be the rate determining step. Royal Society of Chemistry 2017-03-01 2016-12-20 /pmc/articles/PMC5369400/ /pubmed/28451350 http://dx.doi.org/10.1039/c6sc05026c Text en This journal is © The Royal Society of Chemistry 2017 http://creativecommons.org/licenses/by-nc/3.0/ This is an Open Access article distributed under the terms of the Creative Commons Attribution-NonCommercial 3.0 Unported License (http://creativecommons.org/licenses/by-nc/3.0/) which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited.
spellingShingle Chemistry
Barsu, Nagaraju
Bolli, Shyam Kumar
Sundararaju, Basker
Cobalt catalyzed carbonylation of unactivated C(sp(3))–H bonds
title Cobalt catalyzed carbonylation of unactivated C(sp(3))–H bonds
title_full Cobalt catalyzed carbonylation of unactivated C(sp(3))–H bonds
title_fullStr Cobalt catalyzed carbonylation of unactivated C(sp(3))–H bonds
title_full_unstemmed Cobalt catalyzed carbonylation of unactivated C(sp(3))–H bonds
title_short Cobalt catalyzed carbonylation of unactivated C(sp(3))–H bonds
title_sort cobalt catalyzed carbonylation of unactivated c(sp(3))–h bonds
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5369400/
https://www.ncbi.nlm.nih.gov/pubmed/28451350
http://dx.doi.org/10.1039/c6sc05026c
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AT sundararajubasker cobaltcatalyzedcarbonylationofunactivatedcsp3hbonds