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Cooperative Polar/Steric Strategy in Achieving Site‐Selective Photocatalyzed C(sp 3 )−H Functionalization
Author(s) -
Yamada Keiichi,
Fukuyama Takahide,
Fujii Saki,
Ravelli Davide,
Fagi Maurizio,
Ryu Ilhyong
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.201701865
Subject(s) - steric effects , chemistry , surface modification , cyclohexanone , photocatalysis , hydrogen bond , photochemistry , methylene , stereochemistry , medicinal chemistry , catalysis , organic chemistry , molecule
Synergistic control over the S H 2 transition states of hydrogen abstraction exploiting polar and steric effects provides a promising cooperative strategy for site‐selective C(sp 3 )−H functionalization using decatungstate anion photocatalysis. By using this photocatalytic approach, the C−H bonds of substituted lactones and cyclic ketones were functionalized selectively. In the remarkable case of 2‐isoamyl 4‐tert‐butyl cyclohexanone ( 1 t ) bearing five methyl, five methylene, and three methine C−H bonds, one methine C−H bond in the isoamyl tether was selectively functionalized.