N-Phthalimide as a Site-Protecting and Stereodirecting Group in Rhodium-Catalyzed C–H Functionalization with Donor/Acceptor Carbenes

[Image: see text] The rhodium-catalyzed enantioselective C–H functionalization of unactivated C–H bonds by means of donor/acceptor carbene-induced C–H insertion was extended to substrates containing nitrogen functionality. The rhodium-stabilized donor/acceptor carbenes were generated by rhodium-cata...

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Autores principales: Chen, Ziyi, Cai, Qinyan, Boni, Yannick T., Liu, Wenbin, Fu, Jiantao, Davies, Huw M. L.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10262272/
https://www.ncbi.nlm.nih.gov/pubmed/37253354
http://dx.doi.org/10.1021/acs.orglett.3c00844
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author Chen, Ziyi
Cai, Qinyan
Boni, Yannick T.
Liu, Wenbin
Fu, Jiantao
Davies, Huw M. L.
author_facet Chen, Ziyi
Cai, Qinyan
Boni, Yannick T.
Liu, Wenbin
Fu, Jiantao
Davies, Huw M. L.
author_sort Chen, Ziyi
collection PubMed
description [Image: see text] The rhodium-catalyzed enantioselective C–H functionalization of unactivated C–H bonds by means of donor/acceptor carbene-induced C–H insertion was extended to substrates containing nitrogen functionality. The rhodium-stabilized donor/acceptor carbenes were generated by rhodium-catalyzed decomposition of aryldiazoacetates. The phthalimido group was the optimum nitrogen protecting group. C–H functionalization at the most sterically accessible methylene site was achieved using Rh(2)(S-2-Cl-5-BrTPCP)(4) as catalyst, whereas Rh(2)(S-TPPTTL)(4) was the most effective catalyst for C–H functionalization at tertiary C–H bonds and for the desymmetrization of N-phthalimidocyclohexane.
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spelling pubmed-102622722023-06-15 N-Phthalimide as a Site-Protecting and Stereodirecting Group in Rhodium-Catalyzed C–H Functionalization with Donor/Acceptor Carbenes Chen, Ziyi Cai, Qinyan Boni, Yannick T. Liu, Wenbin Fu, Jiantao Davies, Huw M. L. Org Lett [Image: see text] The rhodium-catalyzed enantioselective C–H functionalization of unactivated C–H bonds by means of donor/acceptor carbene-induced C–H insertion was extended to substrates containing nitrogen functionality. The rhodium-stabilized donor/acceptor carbenes were generated by rhodium-catalyzed decomposition of aryldiazoacetates. The phthalimido group was the optimum nitrogen protecting group. C–H functionalization at the most sterically accessible methylene site was achieved using Rh(2)(S-2-Cl-5-BrTPCP)(4) as catalyst, whereas Rh(2)(S-TPPTTL)(4) was the most effective catalyst for C–H functionalization at tertiary C–H bonds and for the desymmetrization of N-phthalimidocyclohexane. American Chemical Society 2023-05-30 /pmc/articles/PMC10262272/ /pubmed/37253354 http://dx.doi.org/10.1021/acs.orglett.3c00844 Text en © 2023 American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Chen, Ziyi
Cai, Qinyan
Boni, Yannick T.
Liu, Wenbin
Fu, Jiantao
Davies, Huw M. L.
N-Phthalimide as a Site-Protecting and Stereodirecting Group in Rhodium-Catalyzed C–H Functionalization with Donor/Acceptor Carbenes
title N-Phthalimide as a Site-Protecting and Stereodirecting Group in Rhodium-Catalyzed C–H Functionalization with Donor/Acceptor Carbenes
title_full N-Phthalimide as a Site-Protecting and Stereodirecting Group in Rhodium-Catalyzed C–H Functionalization with Donor/Acceptor Carbenes
title_fullStr N-Phthalimide as a Site-Protecting and Stereodirecting Group in Rhodium-Catalyzed C–H Functionalization with Donor/Acceptor Carbenes
title_full_unstemmed N-Phthalimide as a Site-Protecting and Stereodirecting Group in Rhodium-Catalyzed C–H Functionalization with Donor/Acceptor Carbenes
title_short N-Phthalimide as a Site-Protecting and Stereodirecting Group in Rhodium-Catalyzed C–H Functionalization with Donor/Acceptor Carbenes
title_sort n-phthalimide as a site-protecting and stereodirecting group in rhodium-catalyzed c–h functionalization with donor/acceptor carbenes
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10262272/
https://www.ncbi.nlm.nih.gov/pubmed/37253354
http://dx.doi.org/10.1021/acs.orglett.3c00844
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