Synergistic control over the SH2 transition states of hydrogen abstraction exploiting polar and steric effects provides a promising cooperative strategy for site‐selective C(sp3)−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.

Cooperative Polar/Steric Strategy in Achieving Site-Selective Photocatalyzed C(sp3)-H Functionalization

RAVELLI, DAVIDE;FAGNONI, MAURIZIO;
2017-01-01

Abstract

Synergistic control over the SH2 transition states of hydrogen abstraction exploiting polar and steric effects provides a promising cooperative strategy for site‐selective C(sp3)−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.
2017
The Organic Chemistry/Polymer Science category includes resources concerned with the related fields of organic chemistry and polymer science. The organic chemistry resources deal with compounds of carbon with the exception of certain simple ones, such as the carbon oxides, carbonates, cyanides and cyanates (see Inorganic & Nuclear Chemistry). This category includes research on synthetic and natural organic compounds that may include other elements, such as hydrogen and oxygen, but also nitrogen, halogens, sulphur and phosphorous. Resources concerned with hydrocarbons, organic compounds containing only the elements carbon and hydrogen, are also included in this category. Examples are the alkanes, alkenes, alkynes and aromatics, such as benzene and naphthalene. Polymer science includes all resources dealing with the study, production and technology of polymers, which are compounds composed of very large molecules made up of repeating molecular units (monomers). Polymers may be natural substances, such as polysaccharides or proteins, or synthetic materials, such as nylon or polyethylene.
Esperti anonimi
Inglese
Internazionale
ELETTRONICO
23
36
8615
8618
4
photocatalysis, decatungstate salts, Polar/Steric effects, C(sp3)-H Functionalization
https://doi.org/10.1002/chem.201701865
6
info:eu-repo/semantics/article
262
Yamada, K; Fukuyama, T; Fujii, S; Ravelli, Davide; Fagnoni, Maurizio; Ryu, I.
1 Contributo su Rivista::1.1 Articolo in rivista
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11571/1180971
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