A novel and efficient copper-catalyzed cascade cyclization/trifluoromethylthiolation of unactivated olefins has been achieved with the stable and readily available AgSCF as the SCF source. A range of SCF-substituted pyrrolines have been easily obtained under mild conditions in good yields via the present process. This method represents a facile and rapid access to valuable pyrrolines with fluorine-containing groups, and it is amenable to gram-scale synthesis.
A novel transition‐metal‐free iminotrifluoromethylation of unsaturated oxime esters has been achieved through Rhodamine B photoredox catalysis under mild conditions. This methodology provides facile access to various CF3‐tethered pyrroline derivatives in high efficiency. The gram‐scale reaction demonstrates the potential value of this protocol in organic synthesis.
A photoredox catalyzed trifluoromethyl radical‐triggered trifunctionalization of 5‐hexenenitriles via cyano group migration is reported. The cyano group migration is of high chemo‐selectivity even in the presence of aryl or heteroaryl groups as competitors. This protocol provides a facile access to a broad scope of CF3‐containing compounds with high molecular complexity and functional group diversity. The success of gram‐scale reaction and the versatility of products in derivative synthesis illustrate the potential value of this transformation in synthetic chemistry.
A mild and highly efficient Cu‐catalyzed cascade cyclization/thiocyanation of unactivated alkenes bearing hydrazones has been developed. A broad range of SCN‐substituted pyrazolines have been readily obtained in good to excellent yields with commercially available and very cheap Cu(acac)2 and NH4SCN. This present method provides a rapid, facile, and practical access to valuable pyrazolines with the important SCN functionality, and it is amenable to the gram scale.
A visible‐light photoredox‐catalyzed tandem trifluoromethylation/cyclization/remote oxidation of 1,6‐dienes has been achieved. A broad range of trifluoromethyl group‐containing tetrahydrofurans or tetrahydropyrroles could be generated in good yields and with excellent diastereoselectivity by using dimethyl sulfoxide (DMSO) as the oxidant. The mild and facile protocol affords direct access to trifluoromethyl group‐bearing tetrahydrofurans and tetrahydropyrroles via difunctionalization of olefins.magnified image
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.