Cargando…

Nickel-Catalyzed Amidoalkylation Reaction of γ-Hydroxy Lactams: An Access to 3-Substituted Isoindolinones†

[Image: see text] An efficient Ni(ClO(4))(2)·6H(2)O-promoted amidoalkylation reaction for the synthesis of 3-substituted isoindolinones involving various γ-hydroxy lactams and nucleophiles has been successfully developed. The transformation proceeds with both carbon (ketones and arenes) and heteroat...

Descripción completa

Detalles Bibliográficos
Autores principales: Zhang, Shuo, Shi, Xinhua, Li, Jichao, Hou, Zitong, Song, Zihe, Su, Xiaofeng, Peng, Dan, Wang, Feng, Yu, Yitao, Zhao, Guilong
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2019
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6868882/
https://www.ncbi.nlm.nih.gov/pubmed/31763566
http://dx.doi.org/10.1021/acsomega.9b02853
_version_ 1783472366013120512
author Zhang, Shuo
Shi, Xinhua
Li, Jichao
Hou, Zitong
Song, Zihe
Su, Xiaofeng
Peng, Dan
Wang, Feng
Yu, Yitao
Zhao, Guilong
author_facet Zhang, Shuo
Shi, Xinhua
Li, Jichao
Hou, Zitong
Song, Zihe
Su, Xiaofeng
Peng, Dan
Wang, Feng
Yu, Yitao
Zhao, Guilong
author_sort Zhang, Shuo
collection PubMed
description [Image: see text] An efficient Ni(ClO(4))(2)·6H(2)O-promoted amidoalkylation reaction for the synthesis of 3-substituted isoindolinones involving various γ-hydroxy lactams and nucleophiles has been successfully developed. The transformation proceeds with both carbon (ketones and arenes) and heteroatom (alcohols, thiols, and amines) nucleophiles and in both intermolecular and intramolecular manners. The prominent features of the present strategy are wide substrate scope, excellent group tolerability, and moderate to good yields (up to 96% yield). The present strategy is also characterized by remarkable superiority over the current synthetic methods. Furthermore, the reaction could be scaled up to the multigram scale.
format Online
Article
Text
id pubmed-6868882
institution National Center for Biotechnology Information
language English
publishDate 2019
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-68688822019-11-22 Nickel-Catalyzed Amidoalkylation Reaction of γ-Hydroxy Lactams: An Access to 3-Substituted Isoindolinones† Zhang, Shuo Shi, Xinhua Li, Jichao Hou, Zitong Song, Zihe Su, Xiaofeng Peng, Dan Wang, Feng Yu, Yitao Zhao, Guilong ACS Omega [Image: see text] An efficient Ni(ClO(4))(2)·6H(2)O-promoted amidoalkylation reaction for the synthesis of 3-substituted isoindolinones involving various γ-hydroxy lactams and nucleophiles has been successfully developed. The transformation proceeds with both carbon (ketones and arenes) and heteroatom (alcohols, thiols, and amines) nucleophiles and in both intermolecular and intramolecular manners. The prominent features of the present strategy are wide substrate scope, excellent group tolerability, and moderate to good yields (up to 96% yield). The present strategy is also characterized by remarkable superiority over the current synthetic methods. Furthermore, the reaction could be scaled up to the multigram scale. American Chemical Society 2019-11-05 /pmc/articles/PMC6868882/ /pubmed/31763566 http://dx.doi.org/10.1021/acsomega.9b02853 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 Zhang, Shuo
Shi, Xinhua
Li, Jichao
Hou, Zitong
Song, Zihe
Su, Xiaofeng
Peng, Dan
Wang, Feng
Yu, Yitao
Zhao, Guilong
Nickel-Catalyzed Amidoalkylation Reaction of γ-Hydroxy Lactams: An Access to 3-Substituted Isoindolinones†
title Nickel-Catalyzed Amidoalkylation Reaction of γ-Hydroxy Lactams: An Access to 3-Substituted Isoindolinones†
title_full Nickel-Catalyzed Amidoalkylation Reaction of γ-Hydroxy Lactams: An Access to 3-Substituted Isoindolinones†
title_fullStr Nickel-Catalyzed Amidoalkylation Reaction of γ-Hydroxy Lactams: An Access to 3-Substituted Isoindolinones†
title_full_unstemmed Nickel-Catalyzed Amidoalkylation Reaction of γ-Hydroxy Lactams: An Access to 3-Substituted Isoindolinones†
title_short Nickel-Catalyzed Amidoalkylation Reaction of γ-Hydroxy Lactams: An Access to 3-Substituted Isoindolinones†
title_sort nickel-catalyzed amidoalkylation reaction of γ-hydroxy lactams: an access to 3-substituted isoindolinones†
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6868882/
https://www.ncbi.nlm.nih.gov/pubmed/31763566
http://dx.doi.org/10.1021/acsomega.9b02853
work_keys_str_mv AT zhangshuo nickelcatalyzedamidoalkylationreactionofghydroxylactamsanaccessto3substitutedisoindolinones
AT shixinhua nickelcatalyzedamidoalkylationreactionofghydroxylactamsanaccessto3substitutedisoindolinones
AT lijichao nickelcatalyzedamidoalkylationreactionofghydroxylactamsanaccessto3substitutedisoindolinones
AT houzitong nickelcatalyzedamidoalkylationreactionofghydroxylactamsanaccessto3substitutedisoindolinones
AT songzihe nickelcatalyzedamidoalkylationreactionofghydroxylactamsanaccessto3substitutedisoindolinones
AT suxiaofeng nickelcatalyzedamidoalkylationreactionofghydroxylactamsanaccessto3substitutedisoindolinones
AT pengdan nickelcatalyzedamidoalkylationreactionofghydroxylactamsanaccessto3substitutedisoindolinones
AT wangfeng nickelcatalyzedamidoalkylationreactionofghydroxylactamsanaccessto3substitutedisoindolinones
AT yuyitao nickelcatalyzedamidoalkylationreactionofghydroxylactamsanaccessto3substitutedisoindolinones
AT zhaoguilong nickelcatalyzedamidoalkylationreactionofghydroxylactamsanaccessto3substitutedisoindolinones