Chemodivergent photocatalytic access to 1-pyrrolines and 1-tetralones involving switchable C(sp(3))–H functionalization

A chemodivergent photocatalytic approach to 1-pyrrolines and 1-tetralones from alkyl bromides and vinyl azides has been developed through chemoselectively controllable intermolecular [3 + 2] and [4 + 2] cyclization. This photoredox-neutral two-component protocol involves intermolecular radical addit...

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Autores principales: Tu, Shijing, Qi, Zhongyu, Li, Weicai, Zhang, Shiqi, Zhang, Zhijie, Wei, Jun, Yang, Lin, Wei, Siping, Du, Xi, Yi, Dong
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Frontiers Media S.A. 2022
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9641198/
https://www.ncbi.nlm.nih.gov/pubmed/36385998
http://dx.doi.org/10.3389/fchem.2022.1058596
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author Tu, Shijing
Qi, Zhongyu
Li, Weicai
Zhang, Shiqi
Zhang, Zhijie
Wei, Jun
Yang, Lin
Wei, Siping
Du, Xi
Yi, Dong
author_facet Tu, Shijing
Qi, Zhongyu
Li, Weicai
Zhang, Shiqi
Zhang, Zhijie
Wei, Jun
Yang, Lin
Wei, Siping
Du, Xi
Yi, Dong
author_sort Tu, Shijing
collection PubMed
description A chemodivergent photocatalytic approach to 1-pyrrolines and 1-tetralones from alkyl bromides and vinyl azides has been developed through chemoselectively controllable intermolecular [3 + 2] and [4 + 2] cyclization. This photoredox-neutral two-component protocol involves intermolecular radical addition and switchable distal C(sp(3))–H functionalization enabled by iminyl radical-mediated 1,5-hydrogen atom transfer. Meanwhile, chemoselectivity between C(sp(3))–N bond formation and C(sp(3))–C(sp(2)) bond formation is precisely switched by photocatalysts (Ru(bpy)(3)(PF(6))(2) vs. fac-Ir(ppy)(3)) and additives (base vs. acid).
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spelling pubmed-96411982022-11-15 Chemodivergent photocatalytic access to 1-pyrrolines and 1-tetralones involving switchable C(sp(3))–H functionalization Tu, Shijing Qi, Zhongyu Li, Weicai Zhang, Shiqi Zhang, Zhijie Wei, Jun Yang, Lin Wei, Siping Du, Xi Yi, Dong Front Chem Chemistry A chemodivergent photocatalytic approach to 1-pyrrolines and 1-tetralones from alkyl bromides and vinyl azides has been developed through chemoselectively controllable intermolecular [3 + 2] and [4 + 2] cyclization. This photoredox-neutral two-component protocol involves intermolecular radical addition and switchable distal C(sp(3))–H functionalization enabled by iminyl radical-mediated 1,5-hydrogen atom transfer. Meanwhile, chemoselectivity between C(sp(3))–N bond formation and C(sp(3))–C(sp(2)) bond formation is precisely switched by photocatalysts (Ru(bpy)(3)(PF(6))(2) vs. fac-Ir(ppy)(3)) and additives (base vs. acid). Frontiers Media S.A. 2022-10-25 /pmc/articles/PMC9641198/ /pubmed/36385998 http://dx.doi.org/10.3389/fchem.2022.1058596 Text en Copyright © 2022 Tu, Qi, Li, Zhang, Zhang, Wei, Yang, Wei, Du and Yi. https://creativecommons.org/licenses/by/4.0/This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner(s) are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms.
spellingShingle Chemistry
Tu, Shijing
Qi, Zhongyu
Li, Weicai
Zhang, Shiqi
Zhang, Zhijie
Wei, Jun
Yang, Lin
Wei, Siping
Du, Xi
Yi, Dong
Chemodivergent photocatalytic access to 1-pyrrolines and 1-tetralones involving switchable C(sp(3))–H functionalization
title Chemodivergent photocatalytic access to 1-pyrrolines and 1-tetralones involving switchable C(sp(3))–H functionalization
title_full Chemodivergent photocatalytic access to 1-pyrrolines and 1-tetralones involving switchable C(sp(3))–H functionalization
title_fullStr Chemodivergent photocatalytic access to 1-pyrrolines and 1-tetralones involving switchable C(sp(3))–H functionalization
title_full_unstemmed Chemodivergent photocatalytic access to 1-pyrrolines and 1-tetralones involving switchable C(sp(3))–H functionalization
title_short Chemodivergent photocatalytic access to 1-pyrrolines and 1-tetralones involving switchable C(sp(3))–H functionalization
title_sort chemodivergent photocatalytic access to 1-pyrrolines and 1-tetralones involving switchable c(sp(3))–h functionalization
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9641198/
https://www.ncbi.nlm.nih.gov/pubmed/36385998
http://dx.doi.org/10.3389/fchem.2022.1058596
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