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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Detalles Bibliográficos
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
Descripción
Sumario: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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