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Upstream product

• 1122-91-4 4-bromo-benzaldehyde 
• 100-46-9 benzylamine 
• 55096-89-4 N-benzyl-1-(4-bromophenyl)methanamine 

Downstream Products

• 80311-89-3 4-bromo-N-benzylbenzamide 
• 27845-50-7 (E)-N-benzylidenebenzylamine 

Relevant academic research and scientific papers

Preparation of homoallylic amines via a three-component coupling process

A three-component synthesis of homoallylic amines is described. The allylboronic species were generated in situ by homologation of vinyl boroxines with trimethylsilyldiazomethane, then followed by trapping of the allylboron intermediate with imines. Twenty-seven compounds were successfully prepared in moderate to high yields. Imines bearing various functional groups were tolerated, including aliphatic, aromatic and heteroaromatic substituents. Further elaboration of some of the homoallylic amines to form azeditines is also reported.

Trans-Symmetric Dynamic Covalent Systems: Connected Transamination and Transimination Reactions

The development of chemical transaminations as a new type of dynamic covalent reaction is described. The key 1,3-proton shift is under complete catalytic control and can be conducted orthogonally to, or simultaneous with, transimination in the presence of an amine to rapidly yield two-dimensional dynamic systems with a high degree of complexity evolution. The transamination-transimination systems are proven to be fully reversible, stable over several days, compatible with a range of functional groups, and highly tunable. Kinetic studies show transamination to be the rate-limiting reaction in the network. Furthermore, it was discovered that readily available quinuclidine is a highly potent catalyst for aldimine transaminations. This study demonstrates how connected dynamic reactions give rise to significantly larger systems than the unconnected counterparts, and shows how reversible isomerizations can be utilized as an effective diversity-generating element. Constant exchange: The development of chemical transaminations as a new type of dynamic covalent reactions is described (see figure). This study demonstrates how connected dynamic reactions give rise to significantly larger systems than the unconnected counterparts, and shows how reversible isomerizations can be utilized as an effective diversity-generating element.

An integrated microreactor for the multicomponent synthesis of α-aminonitriles

Initial steps have been taken to develop an integrated microreactor, capable of performing multicomponent reactions consisting of both solution phase and heterogeneously catalyzed steps. Using the multicomponent Strecker reaction as a model, five α-aminonitriles were synthesized in excellent yields (>99.5%) and analytical purity, under continuous flow conditions.

Scandium triflate catalyzed cycloaddition of imines with 1,1-cyclopropanediesters: Efficient and diastereoselective synthesis of multisubstituted pyrrolidines

A tandem ring-opening-cyclization reaction of cyclopropanes with imines in the presence of 5 mol% of scandium triflate was developed for the highly diastereoselective synthesis of multisubstituted pyrrolidines. The Royal Society of Chemistry 2006.

o-Iodoxybenzoic Acid (IBX) as a Viable Reagent in the Manipulation of Nitrogen- and Sulfur-Containing Substrates: Scope, Generality, and Mechanism of IBX-Mediated Amine Oxidations and Dithiane Deprotections

o-Iodoxybenzoic acid (IBX), a highly versatile hypervalent iodine(V) reagent, was found to efficiently mediate the dehydrogenation of amines in addition to facilitating the oxidative cleavage of dithioacetals and dithioketals. Through the development of relevant IBX-based protocols, a plethora of useful synthetic intermediates, including imines, oximes, ketones, and aromatic N-heterocycles, were found to be readily accessible under notably mild conditions. Further investigation of these transformations led to the elucidation of valuable mechanistic details, resulting in the conclusion that they proceed via ionic rather than single electron transfer (SET) pathways.

Oxidation of N-benzylaldimines to N-benzylamides by MCPBA and BF3·OEt2

N-Benzylamides were obtained from the corresponding N-benzylaldimines in high yields. N-Benzylaldimines are readily prepared from the corresponding aldehydes with benzylamine. This procedure involves the oxidation of N-benzylaldimines with MCPBA with BF3·OEt2. In this reaction, the reaction presumably follows an internal hydrogen abstraction to provide only N-benzylamide.