Hydroalkylation of Styrenes with Benzylamines by Potassium Hydride

Abstract

A method for the synthesis of 1,3‐diarylpropylamines through hydroalkylation of styrenes with benzylamines by potassium hydride has been developed. The protocol is initiated by solvothermal treatment of benzylamines with KH at 100 °C to generate deprotonated anionic species, which undergo selective C‐alkylation with arylalkenes at 0 °C to ambient temperature to afford 1,3‐diarylpropylamines as the major product.

Base-Induced Dehydrogenative and Dearomative Transformation of 1-Naphthylmethylamines to 1,4-Dihydronaphthalene-1-carbonitriles

“…Our group has recently reported hydroalkylation of styrenes with benzylamines mediated by potassium hydride (KH) . Solvothermal treatment of benzylamine ( 1 ) with KH at 100 °C in THF forms deprotonated anionic species ( I and II ), which react with styrene ( 2 ) as a C-nucleophile to form 1,3-diarylpropylamine 3 (Scheme A).…”

“…Our group has recently reported hydroalkylation of styrenes with benzylamines mediated by potassium hydride (KH). 17 Solvothermal treatment of benzylamine ( 1) with KH at 100 °C in THF forms deprotonated anionic species (I and II), which react with styrene (2) as a C-nucleophile to form 1,3diarylpropylamine 3 (Scheme 2A). It should be noted that large excess use of benzylamine (1) to KH is essential to keep the anionic species (I and II) derived from deprotonation of benzylamine (1).…”