Selective carboxylation of reactive benzylic C–H bonds by a hypervalent iodine(III)/inorganic bromide oxidation system

An oxidation system comprising phenyliodine(III) diacetate (PIDA) and iodosobenzene with inorganic bromide, i.e., sodium bromide, in an organic solvent led to the direct introduction of carboxylic acids into benzylic C–H bonds under mild conditions. The unique radical species, generated by the homol...

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Detalles Bibliográficos
Autores principales: Dohi, Toshifumi, Ueda, Shohei, Iwasaki, Kosuke, Tsunoda, Yusuke, Morimoto, Koji, Kita, Yasuyuki
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2018
Materias:
Letter
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6009330/
https://www.ncbi.nlm.nih.gov/pubmed/29977380
http://dx.doi.org/10.3762/bjoc.14.94
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author Dohi, Toshifumi
Ueda, Shohei
Iwasaki, Kosuke
Tsunoda, Yusuke
Morimoto, Koji
Kita, Yasuyuki
author_facet Dohi, Toshifumi
Ueda, Shohei
Iwasaki, Kosuke
Tsunoda, Yusuke
Morimoto, Koji
Kita, Yasuyuki
author_sort Dohi, Toshifumi
collection PubMed
description An oxidation system comprising phenyliodine(III) diacetate (PIDA) and iodosobenzene with inorganic bromide, i.e., sodium bromide, in an organic solvent led to the direct introduction of carboxylic acids into benzylic C–H bonds under mild conditions. The unique radical species, generated by the homolytic cleavage of the labile I(III)–Br bond of the in situ-formed bromo-λ(3)-iodane, initiated benzylic carboxylation with a high degree of selectivity for the secondary benzylic position.
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spelling pubmed-60093302018-07-05 Selective carboxylation of reactive benzylic C–H bonds by a hypervalent iodine(III)/inorganic bromide oxidation system Dohi, Toshifumi Ueda, Shohei Iwasaki, Kosuke Tsunoda, Yusuke Morimoto, Koji Kita, Yasuyuki Beilstein J Org Chem Letter An oxidation system comprising phenyliodine(III) diacetate (PIDA) and iodosobenzene with inorganic bromide, i.e., sodium bromide, in an organic solvent led to the direct introduction of carboxylic acids into benzylic C–H bonds under mild conditions. The unique radical species, generated by the homolytic cleavage of the labile I(III)–Br bond of the in situ-formed bromo-λ(3)-iodane, initiated benzylic carboxylation with a high degree of selectivity for the secondary benzylic position. Beilstein-Institut 2018-05-16 /pmc/articles/PMC6009330/ /pubmed/29977380 http://dx.doi.org/10.3762/bjoc.14.94 Text en Copyright © 2018, Dohi et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Letter
Dohi, Toshifumi
Ueda, Shohei
Iwasaki, Kosuke
Tsunoda, Yusuke
Morimoto, Koji
Kita, Yasuyuki
Selective carboxylation of reactive benzylic C–H bonds by a hypervalent iodine(III)/inorganic bromide oxidation system
title Selective carboxylation of reactive benzylic C–H bonds by a hypervalent iodine(III)/inorganic bromide oxidation system
title_full Selective carboxylation of reactive benzylic C–H bonds by a hypervalent iodine(III)/inorganic bromide oxidation system
title_fullStr Selective carboxylation of reactive benzylic C–H bonds by a hypervalent iodine(III)/inorganic bromide oxidation system
title_full_unstemmed Selective carboxylation of reactive benzylic C–H bonds by a hypervalent iodine(III)/inorganic bromide oxidation system
title_short Selective carboxylation of reactive benzylic C–H bonds by a hypervalent iodine(III)/inorganic bromide oxidation system
title_sort selective carboxylation of reactive benzylic c–h bonds by a hypervalent iodine(iii)/inorganic bromide oxidation system
topic Letter
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6009330/
https://www.ncbi.nlm.nih.gov/pubmed/29977380
http://dx.doi.org/10.3762/bjoc.14.94
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