jo9b02502_si_002.cif (544.06 kB)
Photoredox-Mediated Remote C(sp3)–H Heteroarylation of N‑Alkyl Sulfonamides
dataset
posted on 2019-12-10, 20:42 authored by Zhiqiang Deng, Guo-Xing Li, Gang He, Gong ChenA Minisci-type δ-selective C(sp3)–H
heteroarylation
of sulfonyl-protected primary aliphatic amines with N-heteroarenes under photoredox-catalyzed conditions was developed.
The reaction typically uses a slight excess of amine reactant. The
use of benziodoxole acetate (BI-OAc) oxidant and hexafluoroisopropanol
solvent is critical to achieve high yield. Besides methylene C–H
bonds, heteroarylation reactions of δ methyl C–H bonds
also worked under more forced conditions. The reactions show a broad
scope for both amine and N-heteroarene substrates,
offering a straightforward method for synthesis of complex δ-heteroarylalkylmines
from simple precursors.