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Rhodium‐Catalyzed C−H Methylation and Alkylation Reactions by Carbene‐Transfer Reactions

In this combined computational and experimental study, the C−H functionalization of 2‐phenyl pyridine with diazoalkanes was investigated. Initial evaluation by computational methods allowed the evaluation of different metal catalysts and diazoalkanes and their compatibility in this C−H functionaliza...

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Autores principales: Empel, Claire, Jana, Sripati, Langletz, Tim, Koenigs, Rene M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9302633/
https://www.ncbi.nlm.nih.gov/pubmed/35015327
http://dx.doi.org/10.1002/chem.202104321
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author Empel, Claire
Jana, Sripati
Langletz, Tim
Koenigs, Rene M.
author_facet Empel, Claire
Jana, Sripati
Langletz, Tim
Koenigs, Rene M.
author_sort Empel, Claire
collection PubMed
description In this combined computational and experimental study, the C−H functionalization of 2‐phenyl pyridine with diazoalkanes was investigated. Initial evaluation by computational methods allowed the evaluation of different metal catalysts and diazoalkanes and their compatibility in this C−H functionalization reaction. With these findings, suitable reaction conditions for the C−H methylation reactions were quickly identified by using highly reactive TMS diazomethane and C−H alkylation reactions with donor/acceptor diazoalkanes, which is applied to a broad scope on alkylation reactions of 2‐aryl pyridines with TMS diazomethane and donor/acceptor diazoalkane (51 examples, up to 98 % yield).
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spelling pubmed-93026332022-07-22 Rhodium‐Catalyzed C−H Methylation and Alkylation Reactions by Carbene‐Transfer Reactions Empel, Claire Jana, Sripati Langletz, Tim Koenigs, Rene M. Chemistry Research Articles In this combined computational and experimental study, the C−H functionalization of 2‐phenyl pyridine with diazoalkanes was investigated. Initial evaluation by computational methods allowed the evaluation of different metal catalysts and diazoalkanes and their compatibility in this C−H functionalization reaction. With these findings, suitable reaction conditions for the C−H methylation reactions were quickly identified by using highly reactive TMS diazomethane and C−H alkylation reactions with donor/acceptor diazoalkanes, which is applied to a broad scope on alkylation reactions of 2‐aryl pyridines with TMS diazomethane and donor/acceptor diazoalkane (51 examples, up to 98 % yield). John Wiley and Sons Inc. 2022-02-02 2022-02-24 /pmc/articles/PMC9302633/ /pubmed/35015327 http://dx.doi.org/10.1002/chem.202104321 Text en © 2022 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH https://creativecommons.org/licenses/by-nc/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc/4.0/ (https://creativecommons.org/licenses/by-nc/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes.
spellingShingle Research Articles
Empel, Claire
Jana, Sripati
Langletz, Tim
Koenigs, Rene M.
Rhodium‐Catalyzed C−H Methylation and Alkylation Reactions by Carbene‐Transfer Reactions
title Rhodium‐Catalyzed C−H Methylation and Alkylation Reactions by Carbene‐Transfer Reactions
title_full Rhodium‐Catalyzed C−H Methylation and Alkylation Reactions by Carbene‐Transfer Reactions
title_fullStr Rhodium‐Catalyzed C−H Methylation and Alkylation Reactions by Carbene‐Transfer Reactions
title_full_unstemmed Rhodium‐Catalyzed C−H Methylation and Alkylation Reactions by Carbene‐Transfer Reactions
title_short Rhodium‐Catalyzed C−H Methylation and Alkylation Reactions by Carbene‐Transfer Reactions
title_sort rhodium‐catalyzed c−h methylation and alkylation reactions by carbene‐transfer reactions
topic Research Articles
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9302633/
https://www.ncbi.nlm.nih.gov/pubmed/35015327
http://dx.doi.org/10.1002/chem.202104321
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