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Iron(II)‐Catalyzed Site‐Selective Functionalization of Unactivated C(sp 3 )−H Bonds Guided by Alkoxyl Radicals
Author(s) -
Guan Honghao,
Sun Shutao,
Mao Ying,
Chen Lei,
Lu Ran,
Huang Jiancheng,
Liu Lei
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201806434
Subject(s) - surface modification , chemistry , amination , radical , catalysis , alkoxy group , functional group , methylene , alkane , alkynylation , combinatorial chemistry , photochemistry , organic chemistry , alkyl , polymer
An alkoxyl radical guided strategy for site‐selective functionalization of unactivated methylene and methine C−H bonds enabled by an Fe II ‐catalyzed redox process is described. The mild, expeditious, and modular protocol allows efficient remote aliphatic fluorination, chlorination, amination, and alkynylation of structurally and electronically varied primary, secondary, and tertiary hydroperoxides with excellent functional‐group tolerance. The application for one‐pot 1,4‐hydroxyl functionalization of non‐oxygenated alkane substrates initiated by aerobic C−H oxygenation is also demonstrated.