Frontiers in Chemistry (Oct 2022)

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

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

DOI
https://doi.org/10.3389/fchem.2022.1058596
Journal volume & issue
Vol. 10

Abstract

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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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