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This article is cited in 21 scientific papers (total in 21 papers)
Methods for selective benzylic $\mathrm{C}$–$\mathrm{H}$ oxofunctionalization of organic compounds
D. P. Lubovab, E. P. Talsiab, K. P. Bryliakovab a Novosibirsk State University
b Boreskov Institute of Catalysis SB RAS, Novosibirsk
Abstract:
The development of methods for the selective oxidation of $\mathrm{C}$–$\mathrm{H}$ groups of organic compounds resulting in the formation of $\mathrm{C}$–$\mathrm{O}$ bonds is a challenging problem in modern synthetic organic chemistry. Versatile methods for oxofunctionalization of these groups are currently lacking. Approaches for the oxidation of benzylic $\mathrm{C}$–$\mathrm{H}$ groups having a relatively weak $\mathrm{C}$–$\mathrm{H}$ bond (the homolytic dissociation energy is $\sim80$–$90$ kcal/mol) differ from the methods used for the oxidation of aliphatic and aromatic $\mathrm{C}$–$\mathrm{H}$ groups with stronger $\mathrm{C}$–$\mathrm{H}$ bonds. The review summarizes homogeneous catalytic and non-catalytic methods for the selective oxofunctionalization of benzylic groups of organic compounds developed in the past $40$ years. Reactions involving various oxidizing agents in the presence or in the absence of transition metal compounds are considered. Putative mechanisms of selected transformations are discussed, with a particular focus on selective oxidation of various substrates. The bibliography includes 278 references.
Keywords:
Benzylic, C-H activation, homogeneous catalysis, mechanism, selective oxidation.
Received: 10.08.2019
Citation:
D. P. Lubov, E. P. Talsi, K. P. Bryliakov, “Methods for selective benzylic $\mathrm{C}$–$\mathrm{H}$ oxofunctionalization of organic compounds”, Usp. Khim., 89:6 (2020), 587–628; Russian Chem. Reviews, 89:6 (2020), 587–628
Linking options:
https://www.mathnet.ru/eng/rcr4296https://doi.org/10.1070/RCR4918 https://www.mathnet.ru/eng/rcr/v89/i6/p587
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