Practical Catalytic Cleavage of C(sp(3))−C(sp(3)) Bonds in Amines

The selective cleavage of thermodynamically stable C(sp(3))−C(sp(3)) single bonds is rare compared to their ubiquitous formation. Herein, we describe a general methodology for such transformations using homogeneous copper‐based catalysts in the presence of air. The utility of this novel methodology...

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Detalles Bibliográficos
Autores principales: Li, Wu, Liu, Weiping, Leonard, David K., Rabeah, Jabor, Junge, Kathrin, Brückner, Angelika, Beller, Matthias
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2019
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6771714/
https://www.ncbi.nlm.nih.gov/pubmed/31125156
http://dx.doi.org/10.1002/anie.201903019
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author Li, Wu
Liu, Weiping
Leonard, David K.
Rabeah, Jabor
Junge, Kathrin
Brückner, Angelika
Beller, Matthias
author_facet Li, Wu
Liu, Weiping
Leonard, David K.
Rabeah, Jabor
Junge, Kathrin
Brückner, Angelika
Beller, Matthias
author_sort Li, Wu
collection PubMed
description The selective cleavage of thermodynamically stable C(sp(3))−C(sp(3)) single bonds is rare compared to their ubiquitous formation. Herein, we describe a general methodology for such transformations using homogeneous copper‐based catalysts in the presence of air. The utility of this novel methodology is demonstrated for C(α)−C(β) bond scission in >70 amines with excellent functional group tolerance. This transformation establishes tertiary amines as a general synthon for amides and provides valuable possibilities for their scalable functionalization in, for example, natural products and bioactive molecules.
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spelling pubmed-67717142019-10-07 Practical Catalytic Cleavage of C(sp(3))−C(sp(3)) Bonds in Amines Li, Wu Liu, Weiping Leonard, David K. Rabeah, Jabor Junge, Kathrin Brückner, Angelika Beller, Matthias Angew Chem Int Ed Engl Communications The selective cleavage of thermodynamically stable C(sp(3))−C(sp(3)) single bonds is rare compared to their ubiquitous formation. Herein, we describe a general methodology for such transformations using homogeneous copper‐based catalysts in the presence of air. The utility of this novel methodology is demonstrated for C(α)−C(β) bond scission in >70 amines with excellent functional group tolerance. This transformation establishes tertiary amines as a general synthon for amides and provides valuable possibilities for their scalable functionalization in, for example, natural products and bioactive molecules. John Wiley and Sons Inc. 2019-07-01 2019-07-29 /pmc/articles/PMC6771714/ /pubmed/31125156 http://dx.doi.org/10.1002/anie.201903019 Text en © 2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc-nd/4.0/ License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made.
spellingShingle Communications
Li, Wu
Liu, Weiping
Leonard, David K.
Rabeah, Jabor
Junge, Kathrin
Brückner, Angelika
Beller, Matthias
Practical Catalytic Cleavage of C(sp(3))−C(sp(3)) Bonds in Amines
title Practical Catalytic Cleavage of C(sp(3))−C(sp(3)) Bonds in Amines
title_full Practical Catalytic Cleavage of C(sp(3))−C(sp(3)) Bonds in Amines
title_fullStr Practical Catalytic Cleavage of C(sp(3))−C(sp(3)) Bonds in Amines
title_full_unstemmed Practical Catalytic Cleavage of C(sp(3))−C(sp(3)) Bonds in Amines
title_short Practical Catalytic Cleavage of C(sp(3))−C(sp(3)) Bonds in Amines
title_sort practical catalytic cleavage of c(sp(3))−c(sp(3)) bonds in amines
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6771714/
https://www.ncbi.nlm.nih.gov/pubmed/31125156
http://dx.doi.org/10.1002/anie.201903019
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