AUTHOR=Tu Shijing , Qi Zhongyu , Li Weicai , Zhang Shiqi , Zhang Zhijie , Wei Jun , Yang Lin , Wei Siping , Du Xi , Yi Dong 

TITLE=Chemodivergent photocatalytic access to 1-pyrrolines and 1-tetralones involving switchable C(sp3)–H functionalization

JOURNAL=Frontiers in Chemistry

VOLUME=10

YEAR=2022

URL=https://www.frontiersin.org/journals/chemistry/articles/10.3389/fchem.2022.1058596

DOI=10.3389/fchem.2022.1058596

ISSN=2296-2646

ABSTRACT=<p>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<sup>3</sup>)–H functionalization enabled by iminyl radical-mediated 1,5-hydrogen atom transfer. Meanwhile, chemoselectivity between C(sp<sup>3</sup>)–N bond formation and C(sp<sup>3</sup>)–C(sp<sup>2</sup>) bond formation is precisely switched by photocatalysts (Ru(bpy)<sub>3</sub>(PF<sub>6</sub>)<sub>2</sub> vs. <italic>fac</italic>-Ir(ppy)<sub>3</sub>) and additives (base vs. acid).</p>