Ni-Catalyzed Electrochemical Decarboxylative C–C Couplings in Batch and Continuous Flow

[Image: see text] An electrochemically driven, nickel-catalyzed reductive coupling of N-hydroxyphthalimide esters with aryl halides is reported. The reaction proceeds under mild conditions in a divided electrochemical cell and employs a tertiary amine as the reductant. This decarboxylative C(sp(3))–...

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Autores principales: Li, Hui, Breen, Christopher P., Seo, Hyowon, Jamison, Timothy F., Fang, Yuan-Qing, Bio, Matthew M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2018
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5838802/
https://www.ncbi.nlm.nih.gov/pubmed/29431449
http://dx.doi.org/10.1021/acs.orglett.8b00070
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author Li, Hui
Breen, Christopher P.
Seo, Hyowon
Jamison, Timothy F.
Fang, Yuan-Qing
Bio, Matthew M.
author_facet Li, Hui
Breen, Christopher P.
Seo, Hyowon
Jamison, Timothy F.
Fang, Yuan-Qing
Bio, Matthew M.
author_sort Li, Hui
collection PubMed
description [Image: see text] An electrochemically driven, nickel-catalyzed reductive coupling of N-hydroxyphthalimide esters with aryl halides is reported. The reaction proceeds under mild conditions in a divided electrochemical cell and employs a tertiary amine as the reductant. This decarboxylative C(sp(3))–C(sp(2)) bond-forming transformation exhibits excellent substrate generality and functional group compatibility. An operationally simple continuous-flow version of this transformation using a commercial electrochemical flow reactor represents a robust and scalable synthesis of value added coupling process.
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spelling pubmed-58388022018-03-07 Ni-Catalyzed Electrochemical Decarboxylative C–C Couplings in Batch and Continuous Flow Li, Hui Breen, Christopher P. Seo, Hyowon Jamison, Timothy F. Fang, Yuan-Qing Bio, Matthew M. Org Lett [Image: see text] An electrochemically driven, nickel-catalyzed reductive coupling of N-hydroxyphthalimide esters with aryl halides is reported. The reaction proceeds under mild conditions in a divided electrochemical cell and employs a tertiary amine as the reductant. This decarboxylative C(sp(3))–C(sp(2)) bond-forming transformation exhibits excellent substrate generality and functional group compatibility. An operationally simple continuous-flow version of this transformation using a commercial electrochemical flow reactor represents a robust and scalable synthesis of value added coupling process. American Chemical Society 2018-02-12 2018-03-02 /pmc/articles/PMC5838802/ /pubmed/29431449 http://dx.doi.org/10.1021/acs.orglett.8b00070 Text en Copyright © 2018 American Chemical Society This is an open access article published under a Creative Commons Attribution (CC-BY) License (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html) , which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
spellingShingle Li, Hui
Breen, Christopher P.
Seo, Hyowon
Jamison, Timothy F.
Fang, Yuan-Qing
Bio, Matthew M.
Ni-Catalyzed Electrochemical Decarboxylative C–C Couplings in Batch and Continuous Flow
title Ni-Catalyzed Electrochemical Decarboxylative C–C Couplings in Batch and Continuous Flow
title_full Ni-Catalyzed Electrochemical Decarboxylative C–C Couplings in Batch and Continuous Flow
title_fullStr Ni-Catalyzed Electrochemical Decarboxylative C–C Couplings in Batch and Continuous Flow
title_full_unstemmed Ni-Catalyzed Electrochemical Decarboxylative C–C Couplings in Batch and Continuous Flow
title_short Ni-Catalyzed Electrochemical Decarboxylative C–C Couplings in Batch and Continuous Flow
title_sort ni-catalyzed electrochemical decarboxylative c–c couplings in batch and continuous flow
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5838802/
https://www.ncbi.nlm.nih.gov/pubmed/29431449
http://dx.doi.org/10.1021/acs.orglett.8b00070
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