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Frontispiece: 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 - Reports
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201781062
Subject(s) - surface modification , photoredox catalysis , chemistry , trifluoromethyl , visible spectrum , catalysis , annulation , ring (chemistry) , stereochemistry , medicinal chemistry , photochemistry , organic chemistry , photocatalysis , materials science , alkyl , optoelectronics
Photoredox Catalysis 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. More information can be found in the Communication by L. Zhou et al. on page 2249 ff.