Bring to light: The first visible‐light‐promoted somophilic isocyanide insertion occurs using an iridium photocatalyst. This efficient synthetic approach provides a rapid entry to 6‐alkylated phenanthridine derivatives (see scheme). The reactions proceed at room temperature in good to excellent yields with broad substrate scope and under environmentally friendly conditions.
An electron-donor-acceptor (EDA) complex between Togni's reagent and a tertiary amine has been introduced. The existence of this EDA complex was supported by NMR titration experiments. The hydrotrifluoromethylation of unactivated aliphatic alkenes and alkynes enabled by this EDA complex has also been developed. This hydrotrifluoromethylation protocol is operationally simple and promoted by a tertiary amine.
A conceptually new strategy has been described for the mild, practical, and environmentally friendly preparation of naphthols and furans using a visible-light promoted photoredox neutral approach. These reactions between accessible electron-deficient bromides and commercially available alkynes could be carried out at room temperature in good-to-excellent chemical yields without any external stoichiometric oxidants.
A mild, practical method to prepare α‐sulfonyl and α‐trifluoromethyl ketones from readily available enol acetates and sulfonyl chlorides has been developed using visible‐light photoredox catalysis. The method could be used with a wide range of enol acetates and sulfonyl chlorides, and gave the desired products in satisfactory to excellent yields.
Radical alkynyltrifluoromethylation of alkenes with actylenic triflones has been achieved. This radical chain reaction is initiated by a catalytic amount of an electron-donor-acceptor complex composed of Togni's reagent and N-methylmorpholine. This transformation proceeds under exceptionally mild and operationally simple conditions. A variety of alkenes are compatible in this protocol including aliphatic alkenes, vinyl ethers, enecarbamates, styrenes, and even acrylates, providing diverse β- trifluoromethyl alkynes in good to excellent yields.
A mechanistically new strategy has been described for the simple, practical, and environmentally friendly preparation of 6-(trifluoromethyl)phenanthridine derivatives using ionic isocyanide insertion from biphenyl isocyanide derivatives and Umemoto's reagent. These reactions were promoted only by inorganic base in good-to-excellent chemical yields without any external stoichiometric oxidants and radical initiators.
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