145472-41-9

Upstream product

• 86658-76-6 1-<(4-methyl-phenyl)sulfonyl>-2-methoxy-pyrrolidine 
• 762-72-1 allyl-trimethyl-silane 
• 145472-39-5 1-[(4-methylphenyl)sulfonyl]-2-pyrrolidinol 
• 91645-35-1 (RS)-[1-(toluene-4-sulfonyl)-pyrrolidine-2-yl]-methanol 
• 98-59-9 p-toluenesulfonyl chloride 
• 498-63-5 2-hydroxymethylpyrrolidine 
• 10019-95-1 N-tosylpyrrolidinone 
• 1254328-94-3 (E)-N-(hepta-4,6-dienyl)-4-methylbenzenesulfonamide 
• 127611-47-6 (Z)-7-azidohepta-1,3-diene 
• 127611-49-8 (Z)-hepta-4,6-dien-1-amine 
• 1510846-89-5 (Z)-N-(hepta-4,6-dienyl)-4-methylbenzenesulfonamide 
• 6435-78-5 N-tosylpyrrolidine 
• 1730-25-2 allylmagnesium bromide 

Relevant academic research and scientific papers

Anodic benzylic C(sp3)-H amination: Unified access to pyrrolidines and piperidines

An electrochemical aliphatic C-H amination strategy was developed to access the important heterocyclic motifs of pyrrolidines and piperidines within a uniform reaction protocol. The mechanism of this unprecedented C-H amination strategy involves anodic C-H activation to generate a benzylic cation, which is efficiently trapped by a nitrogen nucleophile. The applicability of the process is demonstrated for 40 examples comprising both 5- and 6-membered ring formations.

Direct Dehydroxylative Coupling Reaction of Alcohols with Organosilanes through Si-X Bond Activation by Halogen Bonding

The combined use of a halogen bond (XB) donor with trimethylsilyl halide was found to be an efficient cocatalytic system for the direct dehydroxylative coupling reaction of alcohol with various nucleophiles, such as allyltrimethylsilane and trimethylcyanide, to give the corresponding adduct in moderate to excellent yields. Detailed control experiments and mechanistic studies revealed that the XB interaction was crucial for the reaction. The application of this coupling reaction is also described.

A heterogeneous mercury salt catalyst stabilized by m-carbaborane

Development of reusable heterogeneous catalysts has attracted a great deal of attention for both environmental and atom-economic reasons. In particular, a considerable amount of work has focused on reusable heavy- and rare-metal catalysts in order to limit the use and/or minimize the generation of problematic metal waste upon disposal. Herein is reported the development of a new polysiloxane-linked m-carbaboranylmercury (SiCB-Hg) catalyst, which can be used for various mercury salt-induced reactions such as the regioselective cyclization of 1,3-dienes and allyl alcohols, the intermolecular amination of allyl alcohols with sulfamates, and the cycloisomerization of alkynes. The catalyst can be completely recovered by simple filtration, with residual mercury in the filtrate 0.001% (nearly the quantitative limit). Furthermore, the catalyst can be reactivated by treatment with aqueous HCl and then AgOTf for reuse.

Palladium(II)-catalyzed intramolecular hydroamination of 1,3-dienes to give homoallylic amines

A pincer for high selectivity: A mild palladium-catalyzed hydroamination of protected amino-1,3-dienes is possible. This highly regioselective reaction employs a tridentate PNP pincer ligand and leads to cyclic and homoallylic protected amines in high yields. Substrates with a wide array of amine protecting groups and diene substitution patterns were cyclized to form five- and six-membered heterocycles. PG=protecting group.

A carbaboranylmercuric salt catalyzed reaction; Highly regioselective cycloisomerization of 1,3-dienes

The combination of carbaboranylmercuric chloride (new type of bulky Lewis acid) and silver triflate efficiently catalyzes cycloisomerization of 1,3-dienes at room temperature. The catalytic system gives allyl-substituted azacycles and cycloalkanes in exce

Synthesis of alkaloid analogues from β-amino alcohols by β-fragmentation of primary alkoxyl radicals

The fragmentation of primary alkoxyl radicals is usually a minor process with respect to hydrogen abstraction and other competing reactions. However, when β-amino alcohols were used as substrates, the scission proceeded in good to excellent yields and no side reactions were observed. The fragmentation can be coupled with an allylation or alkylation reaction, to give alkaloid analogues and functionalized nitrogen heterocycles. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

Synthesis of alkaloids from aminol derivatives by β-fragmentation of primary alkoxyl radicals

The fragmentation of primary alkoxyl radicals, often described as low yielding and plagued by side reactions, proceeded in good to excellent yields when aminol derivatives were used as substrates. Remarkably, no side reactions such as hydrogen abstraction

Carbon-Carbon Bond Formation via N-Tosyliminium Ions

Addition of carbon nucleophiles to cyclic N-tosyliminium ions, derived from α-hydroxy and α-methoxy tosylamides (5a,b and 6a,b, respectively) is described.In general, good to excellent yields were obtained when allyltrimethylsilane, 1-t-butyldimethylsilyl