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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...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Royal Society of Chemistry
2017
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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. |
format | Online Article Text |
id | pubmed-5369400 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2017 |
publisher | Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
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
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title_full | Cobalt catalyzed carbonylation of unactivated C(sp(3))–H bonds
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title_fullStr | Cobalt catalyzed carbonylation of unactivated C(sp(3))–H bonds
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title_full_unstemmed | Cobalt catalyzed carbonylation of unactivated C(sp(3))–H bonds
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title_short | Cobalt catalyzed carbonylation of unactivated C(sp(3))–H bonds
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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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