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Iridium(I)-Catalyzed Isoindolinone-Directed Branched-Selective Aromatic C–H Alkylation with Simple Alkenes

We report an iridium(I)-catalyzed branched-selective C–H alkylation of N-arylisoindolinones with simple alkenes as the alkylating agents. The amide carbonyl group of the isoindolinone motif acts as the directing group to assist the ortho C–H activation of the N-aryl ring. With this atom-economic and...

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Detalles Bibliográficos
Autores principales: Xiong, Maoqian, Shu, Yuhang, Tang, Jie, Yang, Fan, Xing, Dong
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8954050/
https://www.ncbi.nlm.nih.gov/pubmed/35335286
http://dx.doi.org/10.3390/molecules27061923
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author Xiong, Maoqian
Shu, Yuhang
Tang, Jie
Yang, Fan
Xing, Dong
author_facet Xiong, Maoqian
Shu, Yuhang
Tang, Jie
Yang, Fan
Xing, Dong
author_sort Xiong, Maoqian
collection PubMed
description We report an iridium(I)-catalyzed branched-selective C–H alkylation of N-arylisoindolinones with simple alkenes as the alkylating agents. The amide carbonyl group of the isoindolinone motif acts as the directing group to assist the ortho C–H activation of the N-aryl ring. With this atom-economic and highly branched-selective protocol, an array of biologically relevant N-arylisoindolinones were obtained in good yields. Asymmetric control was achieved with up to 87:13 er when a BiPhePhos-like chiral ligand was employed.
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spelling pubmed-89540502022-03-26 Iridium(I)-Catalyzed Isoindolinone-Directed Branched-Selective Aromatic C–H Alkylation with Simple Alkenes Xiong, Maoqian Shu, Yuhang Tang, Jie Yang, Fan Xing, Dong Molecules Article We report an iridium(I)-catalyzed branched-selective C–H alkylation of N-arylisoindolinones with simple alkenes as the alkylating agents. The amide carbonyl group of the isoindolinone motif acts as the directing group to assist the ortho C–H activation of the N-aryl ring. With this atom-economic and highly branched-selective protocol, an array of biologically relevant N-arylisoindolinones were obtained in good yields. Asymmetric control was achieved with up to 87:13 er when a BiPhePhos-like chiral ligand was employed. MDPI 2022-03-16 /pmc/articles/PMC8954050/ /pubmed/35335286 http://dx.doi.org/10.3390/molecules27061923 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Xiong, Maoqian
Shu, Yuhang
Tang, Jie
Yang, Fan
Xing, Dong
Iridium(I)-Catalyzed Isoindolinone-Directed Branched-Selective Aromatic C–H Alkylation with Simple Alkenes
title Iridium(I)-Catalyzed Isoindolinone-Directed Branched-Selective Aromatic C–H Alkylation with Simple Alkenes
title_full Iridium(I)-Catalyzed Isoindolinone-Directed Branched-Selective Aromatic C–H Alkylation with Simple Alkenes
title_fullStr Iridium(I)-Catalyzed Isoindolinone-Directed Branched-Selective Aromatic C–H Alkylation with Simple Alkenes
title_full_unstemmed Iridium(I)-Catalyzed Isoindolinone-Directed Branched-Selective Aromatic C–H Alkylation with Simple Alkenes
title_short Iridium(I)-Catalyzed Isoindolinone-Directed Branched-Selective Aromatic C–H Alkylation with Simple Alkenes
title_sort iridium(i)-catalyzed isoindolinone-directed branched-selective aromatic c–h alkylation with simple alkenes
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8954050/
https://www.ncbi.nlm.nih.gov/pubmed/35335286
http://dx.doi.org/10.3390/molecules27061923
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AT tangjie iridiumicatalyzedisoindolinonedirectedbranchedselectivearomaticchalkylationwithsimplealkenes
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