Aerobic Oxidation of Benzylic Carbons Using a Guanidine Base

[Image: see text] Metal-free reaction conditions featuring oxygen and 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) were employed for the selective oxidation of benzyl amines and active methylene compounds to afford various amides and ketones. Owing to the strong basicity of guanidine bases, TBD is pres...

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Autores principales: Lee, Seulchan, Kim, Si Ae, Jang, Hye-Young
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2019
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6822219/
https://www.ncbi.nlm.nih.gov/pubmed/31681903
http://dx.doi.org/10.1021/acsomega.9b03064
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author Lee, Seulchan
Kim, Si Ae
Jang, Hye-Young
author_facet Lee, Seulchan
Kim, Si Ae
Jang, Hye-Young
author_sort Lee, Seulchan
collection PubMed
description [Image: see text] Metal-free reaction conditions featuring oxygen and 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) were employed for the selective oxidation of benzyl amines and active methylene compounds to afford various amides and ketones. Owing to the strong basicity of guanidine bases, TBD is presumed to play an important role in the cleavage of the C–H bond at the benzylic position of peroxide intermediates, which were formed by the reaction with oxygen.
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spelling pubmed-68222192019-11-01 Aerobic Oxidation of Benzylic Carbons Using a Guanidine Base Lee, Seulchan Kim, Si Ae Jang, Hye-Young ACS Omega [Image: see text] Metal-free reaction conditions featuring oxygen and 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) were employed for the selective oxidation of benzyl amines and active methylene compounds to afford various amides and ketones. Owing to the strong basicity of guanidine bases, TBD is presumed to play an important role in the cleavage of the C–H bond at the benzylic position of peroxide intermediates, which were formed by the reaction with oxygen. American Chemical Society 2019-10-15 /pmc/articles/PMC6822219/ /pubmed/31681903 http://dx.doi.org/10.1021/acsomega.9b03064 Text en Copyright © 2019 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 Lee, Seulchan
Kim, Si Ae
Jang, Hye-Young
Aerobic Oxidation of Benzylic Carbons Using a Guanidine Base
title Aerobic Oxidation of Benzylic Carbons Using a Guanidine Base
title_full Aerobic Oxidation of Benzylic Carbons Using a Guanidine Base
title_fullStr Aerobic Oxidation of Benzylic Carbons Using a Guanidine Base
title_full_unstemmed Aerobic Oxidation of Benzylic Carbons Using a Guanidine Base
title_short Aerobic Oxidation of Benzylic Carbons Using a Guanidine Base
title_sort aerobic oxidation of benzylic carbons using a guanidine base
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6822219/
https://www.ncbi.nlm.nih.gov/pubmed/31681903
http://dx.doi.org/10.1021/acsomega.9b03064
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AT kimsiae aerobicoxidationofbenzyliccarbonsusingaguanidinebase
AT janghyeyoung aerobicoxidationofbenzyliccarbonsusingaguanidinebase

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