Chemodivergent photocatalytic access to 1-pyrrolines and 1-tetralones involving switchable C(sp3)-H functionalization.
Front Chem
; 10: 1058596, 2022.
Article
em En
| MEDLINE
| ID: mdl-36385998
ABSTRACT
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(sp3)-H functionalization enabled by iminyl radical-mediated 1,5-hydrogen atom transfer. Meanwhile, chemoselectivity between C(sp3)-N bond formation and C(sp3)-C(sp2) bond formation is precisely switched by photocatalysts (Ru(bpy)3(PF6)2 vs. fac-Ir(ppy)3) and additives (base vs. acid).
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MEDLINE
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En
Ano de publicação:
2022
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Article