17214-47-0Relevant academic research and scientific papers
Palladium-catalyzed highly selective intramolecular bromoamination of alkenes: Efficient synthesis of substituted pyrrolidines
Zhang, Jingfang,Wang, Xie,Liu, Yulong,Wang, Xiaoyun,He, Wei
, (2017/05/22)
A new method has been developed for the preparation of substituted pyrrolidines by the palladium-catalyzed intramolecular bromoamination of substituted aminoalkenes. The catalytic system and reaction conditions used for this transformation have been fully optimized. Notably, this reaction exhibits excellent selectivity, affording the pyrrolidine products as single 5-exo-bromoalkylpyrrolidines in excellent yields. Furthermore, this reaction occurs at room temperature under mild conditions, reaching completion within 1?h.
Reactions of Allylic Grignard Reagents and Unsaturated Amines
Richey, Herman G.,Moses, L. Meredith,Domalski, M.S.,Erickson, Wayne F.,Heyn, Alan S.
, p. 3773 - 3780 (2007/10/02)
Reactions were studied of allylic Grignard reagents with allylic and propargylic amines.Additions were observed to N-allylaniline (1), cinnamylamine (6), N,N-dimethylcinnamylamine (10), and 3-(dimethylamino)-1-phenyl-1-propyne (12) but not to allylamine, diallylamine, N-allyl-N-methylaniline, N,N-dimethylallylamine, or N,N-diethylallylamine.Reactions of 3-amino-1-phenyl-1-propyne (8) furnished phenylacetylene rather than an addition product.By comparing reactivities of the amines and comparablehydrocarbons, it is concluded that tertiary amino functions and metalated primary and secondary amino functions can assist Grignard reagent additions to alkene and alkyne functions.Comparisons of reactivities of theunsaturated amines and comparable alcohols suggest that assistance by a metalated amino function is less effective than by a metalated hydroxyl function but more effective than by a tertiary amino function.Another comparison suggests that a metalated phenylamino group is more effective than a metalated primary amino group.
