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Difunctionalization of Olefins by Radicals and Nucleophiles

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Liu,  Sensheng
Research Group Klußmann, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Liu, S. (2021). Difunctionalization of Olefins by Radicals and Nucleophiles. PhD Thesis, Universität zu Köln, Köln.


Cite as: https://hdl.handle.net/21.11116/0000-0009-BB67-1
Abstract
Transition metal free, difunctionalization of olefins by radical and nucleophile is presented in this PhD's work. The combination of benzoyl peroxide with strong Brønsted acid HPF6 allows the
difunctionalizationn of alkenes with radicals derived from thioxanthene, xanthene and
thiophenols together with nitrile and alcohol nucleophiles. Mechanistic studies suggest the acid
promotes the electron transfer step by making BPO as a better electron acceptor.
By using of triarylamine as organo-redox catalyst under transition metal and acid free in
difunctionalization of alkenes was further studied. BPO with catalytic amount of
triarylamine, alkenes can be difunctionalized by a wide range of alkyl radical, generated
from C(sp3)-H or halogenated hydrocarbon, nucleophiles, including nitriles, acetic acid,
alcohols and fluoride. Moreover, the oxidative Ritter reaction of allylic or benzylic C-H bonds
can be also achieved under this reaction system.