Divergent cyanoalkylation/cyanoalkylsulfonylation of enamides under organophotoredox catalytic conditions

Abstract

An organophotoredox-catalyzed divergent cyanoalkylation /cyanoalkylsulfonylation of enamides in a highly regio- and stereoselective manner has been reported. In this mild and efficient protocol, cyclobutanone oxime esters serve as cyanoalkylating source...

Recent advances in ring-opening of cyclobutanone oximes for capturing SO2, CO or O2via a radical process

“…41 Meanwhile, Akondi's group used enamides 14 instead of alkenes 2 and accomplished cyanoalkylsulfonylation of enamides 14 with cyclobutanone oxime esters 1, using K 2 S 2 O 5 as a sulfur dioxide surrogate (Scheme 7). 42 This radical tandem reaction proceeds with excellent regio-and stereoselectivity to generate diverse (E)-β-(sulfonyl)enamines 15 under organophotoredox catalytic rose bengal conditions. Based on the result of control experiments, a similar process of photoredox-catalyzed cyanoalkylsulfonylation of enamides involves C-C bond cleavage of cyclobutanone oxime esters, insertion of sulfur dioxide and deprotonation of the cation intermediate.…”

Ferrocene catalyzed carbohydroxylation of alkenes using H2O and cycloketone oxime esters

“…Additionally, photochemically enabled direct carbohydroxylation of alkenes was achieved by the Zeitler, 11 Heinrich 12 and Chen's 13 groups. Building upon the recent success of our group in the carbo-imidation of alkenes using ferrocene (Cp 2 Fe) catalysis, 14 we envision the possibility of achieving cyanoalkyl-hydroxylation of aryl alkenes using cycloketone oxime esters and a solvent mixture composed of water.…”