16256-47-6Relevant articles and documents
Photoredox-Catalyzed Cα-H Cyanation of Unactivated Secondary and Tertiary Aliphatic Amines: Late-Stage Functionalization and Mechanistic Studies
Yilmaz, Ozgur,Oderinde, Martins S.,Emmert, Marion H.
, p. 11089 - 11100 (2018/09/12)
This paper describes the development and mechanistic studies of a general, high-yielding amine Cα-H cyanation protocol via photoredox catalysis. Inexpensive NaCN is employed as the cyanide source and air is the external oxidant, resulting in mild and highly functional group tolerant conditions. Notably, efficient Cα-H cyanations of secondary and tertiary aliphatic amines and of complex, biologically active compounds (drugs) can be performed using the established methodology. Mechanistic studies suggest that the carboxylic acid additive has three effects: formation of a stabilizing hemiaminal intermediate, prevention of catalyst decomposition by protonating the substrate, and modulation of fluorescence quenching of the photoexcited catalyst species.
Synthesis of a variety of 2-alkyl-2-azabicyclo[31.1]heptane-1-carbonitriles via a dynamic addition-intramolecular substitution sequence
De Blieck, Ann,Stevens, Christian V.
supporting information; experimental part, p. 1748 - 1752 (2011/09/20)
An improved two-step synthetic approach towards 3-(2-chloroethyl) cyclobutanone is described and used in the synthesis of a class of 2-alkyl-2-azabicyclo[3.1.1]heptane-1-carbonitriles. The key step consists of a reversible addition of hydrogen cyanide ont
