6284-07-7Relevant academic research and scientific papers
Reaction of O-Benzyl-N-methylenehydroxylamine with Organolithium Compounds, a CH2+-NH+ Synthetic Equivalent
Basha, Anwer,Brooks, Dee W.
, p. 305 - 306 (1987)
Lithium carbanions add sequentially to O-benzyl-N-methylenehydroxylamine (1), first at the electrophilic carbon and subsequently, at higher temperature, on the nitrogen with concomitant loss of the benzyloxy group, resulting in a CH2+-NH+ synthetic equivalent, the amines (4) being produced.
Benzylamines via Iron-Catalyzed Direct Amination of Benzyl Alcohols
Yan, Tao,Feringa, Ben L.,Barta, Katalin
, p. 381 - 388 (2016/01/12)
Benzylamines play a prominent role in numerous pharmaceutically active compounds. Thus, the development of novel, sustainable catalytic methodologies to provide access to these privileged structural motifs is of central importance. Herein we describe a systematic study for the construction of a large variety of benzylamines using a well-defined homogeneous iron complex. The methodology consists of the direct coupling of readily available benzyl alcohols with simpler amines through the borrowing hydrogen methodology, producing a variety of substituted secondary and tertiary benzylamines in moderate to excellent yields for the first time with an iron catalyst. Notably, we explore the versatility of this methodology in the one-pot synthesis of nonsymmetric tertiary amines, sequential functionalization of diols with distinctly different amines, and the synthesis of N-benzyl piperidines via various synthetic pathways. In addition, direct conversion of the renewable building block 2,5-furan-dimethanol to pharmaceutically relevant compounds is achieved.
