29110-74-5Relevant articles and documents
Decarboxylative Bromination of Heteroarenes: Initial Mechanistic Insights
Patel, Pritesh R.,Henderson, Scott H.,Roe, Mark S.,Honey, Mark A.
supporting information, p. 1603 - 1607 (2020/09/09)
After an initial report from our laboratory describing metal-free decarboxylative halogenation of various azaheteroarenes, we set out to investigate the possible mechanism by which this chemistry occurs. Evidence from this mechanistic investigation sugges
Visible-light photocatalytic activation of N-chlorosuccinimide by organic dyes for the chlorination of arenes and heteroarenes
Rogers, David A.,Gallegos, Jillian M.,Hopkins, Megan D.,Lignieres, Austin A.,Pitzel, Amy K.,Lamar, Angus A.
, (2019/08/12)
A variety of arenes and heteroarenes are chlorinated in moderate to excellent yields using N-chlorosuccinimide (NCS) under visible-light activated conditions. A screening of known organic dye photocatalysts resulted in the identification of methylene green as the most efficient catalyst to use with NCS. According to mechanistic studies described within, the reaction is speculated to proceed via a single electron oxidation of NCS utilizing methylene green under visible-light photoredox pathway. The photo-oxidation of NCS amplifies the electrophilicity of the chlorine atom of the NCS, thus leading to enhanced reactivity as a chlorinating reagent with aromatic substrates.
An efficient method for the N-debenzylation of aromatic heterocycles
Haddach, Aubrey A.,Kelleman, Audrey,Deaton-Rewolinski, Melissa V.
, p. 399 - 402 (2007/10/03)
The treatment of N-benzylated heterocycles with potassium tert-butoxide/DMSO and oxygen at room temperature cleanly affords N-debenzylated products in high yield. This procedure can be utilized on a variety of functionalized nitrogen-containing heterocycles such as imidazoles, benzimidazoles, pyrazoles, indazoles, carbazoles, and indoles.
