Journal
ACS CATALYSIS
Volume 11, Issue 12, Pages 6810-6815Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.1c01350
Keywords
C-H functionalization; N-oxyl radical; molecular tweezer; expanded porphyrin; PCET
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Funding
- National Natural Science Foundation of China [21908255, 21938001, 21961160741]
- Key-Area Research and Development Program of Guangdong Province [2020B010188001]
- National Key Research and Development Program Nanotechnology Specific Project [2020YFA0210900]
- Local Innovative and Research Teams Project of Guangdong Pearl River Talents Program [2017BT01C102]
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An expanded porphyrin-biscopper hexaphyrin was introduced as a bioinspired molecular tweezer to co-catalyze functionalization of C(sp(3))-H bonds. Theoretical and experimental investigations suggested that the biscopper hexaphyrin served as a molecular tweezer to mimic the enzymatic orientation/proximity effect, efficiently activating the N-hydroxyphthalimide (NHPI) via light-free proton-coupled electron transfer (PCET), at an exceptionally low catalyst loading of 10 mol ppm. The resulting N-oxyl radical (PINO) was versatile for chemoselective C-H oxidation and amination of hydrocarbons.
An expanded porphyrin-biscopper hexaphyrin was introduced as a bioinspired molecular tweezer to co-catalyze functionalization of C(sp(3))-H bonds. Theoretical and experimental investigations suggested that the biscopper hexaphyrin served as a molecular tweezer to mimic the enzymatic orientation/proximity effect, efficiently activating the N-hydroxyphthalimide (NHPI) via light-free proton-coupled electron transfer (PCET), at an exceptionally low catalyst loading of 10 mol ppm. The resulting N-oxyl radical (PINO) was versatile for chemoselective C-H oxidation and amination of hydrocarbons.
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