Single-Electron Transmetalation: Protecting-Group-Independent Synthesis of Secondary Benzylic Alcohol Derivatives via Photoredox/Nickel Dual Catalysis

[Image: see text] Protecting-group-independent cross-coupling of α-alkoxyalkyl- and α-acyloxyalkyltrifluoroborates with aryl and heteroaryl bromides is achieved through application of photoredox/nickel dual catalysis. Reactions occur under exceptionally mild conditions, with outstanding functional g...

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Autores principales: Karimi-Nami, Rahman, Tellis, John C., Molander, Gary A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2016
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4900145/
https://www.ncbi.nlm.nih.gov/pubmed/27218884
http://dx.doi.org/10.1021/acs.orglett.6b00911
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author Karimi-Nami, Rahman
Tellis, John C.
Molander, Gary A.
author_facet Karimi-Nami, Rahman
Tellis, John C.
Molander, Gary A.
author_sort Karimi-Nami, Rahman
collection PubMed
description [Image: see text] Protecting-group-independent cross-coupling of α-alkoxyalkyl- and α-acyloxyalkyltrifluoroborates with aryl and heteroaryl bromides is achieved through application of photoredox/nickel dual catalysis. Reactions occur under exceptionally mild conditions, with outstanding functional group compatibility and excellent observed tolerance of heteroarenes. This method offers expedient access to protected secondary benzylic alcohol motifs bearing benzyl, pivaloyl, and N,N-diisopropylcarbamoyl protecting groups.
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spelling pubmed-49001452017-05-24 Single-Electron Transmetalation: Protecting-Group-Independent Synthesis of Secondary Benzylic Alcohol Derivatives via Photoredox/Nickel Dual Catalysis Karimi-Nami, Rahman Tellis, John C. Molander, Gary A. Org Lett [Image: see text] Protecting-group-independent cross-coupling of α-alkoxyalkyl- and α-acyloxyalkyltrifluoroborates with aryl and heteroaryl bromides is achieved through application of photoredox/nickel dual catalysis. Reactions occur under exceptionally mild conditions, with outstanding functional group compatibility and excellent observed tolerance of heteroarenes. This method offers expedient access to protected secondary benzylic alcohol motifs bearing benzyl, pivaloyl, and N,N-diisopropylcarbamoyl protecting groups. American Chemical Society 2016-05-24 2016-06-03 /pmc/articles/PMC4900145/ /pubmed/27218884 http://dx.doi.org/10.1021/acs.orglett.6b00911 Text en Copyright © 2016 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Karimi-Nami, Rahman
Tellis, John C.
Molander, Gary A.
Single-Electron Transmetalation: Protecting-Group-Independent Synthesis of Secondary Benzylic Alcohol Derivatives via Photoredox/Nickel Dual Catalysis
title Single-Electron Transmetalation: Protecting-Group-Independent Synthesis of Secondary Benzylic Alcohol Derivatives via Photoredox/Nickel Dual Catalysis
title_full Single-Electron Transmetalation: Protecting-Group-Independent Synthesis of Secondary Benzylic Alcohol Derivatives via Photoredox/Nickel Dual Catalysis
title_fullStr Single-Electron Transmetalation: Protecting-Group-Independent Synthesis of Secondary Benzylic Alcohol Derivatives via Photoredox/Nickel Dual Catalysis
title_full_unstemmed Single-Electron Transmetalation: Protecting-Group-Independent Synthesis of Secondary Benzylic Alcohol Derivatives via Photoredox/Nickel Dual Catalysis
title_short Single-Electron Transmetalation: Protecting-Group-Independent Synthesis of Secondary Benzylic Alcohol Derivatives via Photoredox/Nickel Dual Catalysis
title_sort single-electron transmetalation: protecting-group-independent synthesis of secondary benzylic alcohol derivatives via photoredox/nickel dual catalysis
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4900145/
https://www.ncbi.nlm.nih.gov/pubmed/27218884
http://dx.doi.org/10.1021/acs.orglett.6b00911
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