Premium
Visible‐Light‐Mediated Two‐Fold Unsymmetrical C(sp 3 )−H Functionalization and Double C−F Substitution
Author(s) -
Li Linyong,
Xiao Tiebo,
Chen Haoguo,
Zhou Lei
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201605919
Subject(s) - surface modification , chemistry , trifluoromethyl , annulation , visible spectrum , photoredox catalysis , catalysis , ring (chemistry) , stereochemistry , medicinal chemistry , organic chemistry , materials science , photocatalysis , alkyl , optoelectronics
A visible‐light‐mediated [3+3] annulation of tertiary amines with α‐trifluoromethyl alkenes was developed. The reaction offers a direct route to fluorinated tetrahydropyridines and azabicyclo[3.m.1] frameworks under very mild conditions. This protocol presents a rare example of dual sp 3 C−H functionalization of tertiary amines with the formation of two different C−C bonds (one sp 3 –sp 3 bond, one sp 2 –sp 3 bond). Moreover, two consecutive C−F substitutions in a trifluoromethyl group were achieved in one pot using visible light photoredox catalysis, which enables an unprecedented ring construction.