69957-80-8Relevant academic research and scientific papers
Nickel(II) Catalyzed Hydroboration: A Route to Selective Reduction of Aldehydes and N-Allylimines
Hossain, Istiak,Schmidt, Joseph A. R.
, p. 1877 - 1884 (2020/05/25)
A cationic [(iminophosphine)nickel(allyl)]+ complex was found to be sufficiently electrophilic to activate aldehydes and N-allylimines to undergo hydroboration with pinacolborane (HBpin) under mild reaction conditions. The catalyst displayed excellent selectivity toward aldehydes in the presence of ketones. A wide variety of functional groups were tolerated, including halogens, NO2, CN, OMe, and alkenes for both aldehydes and imines. Electron-rich substrates were found to be significantly more reactive than their electron poor counterparts, a feature that was correlated to their enhanced ability to coordinate to the Lewis acidic nickel center.
Selective hydrosilylation of N-allylimines using a (3-iminophosphine)palladium precatalyst
Tafazolian, Hosein,Schmidt, Joseph A.R.
, p. 685 - 689 (2016/02/18)
Hydrosilylation utilizing a (3-iminophosphine)palladium catalyst leads to the selective reduction of the imine unit of allylimines. Successful reduction of twenty-five different substituted aromatic and alkyl allylimines demonstrated the scope and selecti
SONIC HEDGEHOG MODULATORS
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Paragraph 0966, (2014/04/17)
Sonic Hedgehog modulators and methods of use thereof are provided for.
Ring-closing metathesis of vinyl fluorides towards α-fluorinated α,β-unsaturated lactams and lactones
Marhold, Michael,Stillig, Christian,Fr?hlich, Roland,Haufe, Günter
supporting information, p. 5777 - 5785 (2014/10/15)
Ring-closing olefin metathesis reactions (RCM) using Grubbs II or Hoveyda's catalysts have been applied to a series of N-alkenyl-N-benzyl-α-fluoroacrylamides. α-Fluoro-α,β-unsaturated γ- or δ-lactams incorporating a fluorinated double bond were obtained in moderate to good yields, depending on the nature of substituents on the benzyl ring. The corresponding seven- and eight-membered lactams were not formed under similar conditions. When the N-benzyl group was replaced by an N-tosyl group, the corresponding ε-lactam was also formed in 38% yield. When N-(2-fluoroallyl) derivatives were used instead of fluoroacryloyl derivatives, six-, seven-, and eight-membered N-heterocycles were obtained in low yields. This method was also used to synthesize fluorinated α,β-unsaturated analogues of pyrrolizidine and indolizidine alkaloids from prolinol, and also to synthesize N-benzyl-3-fluoroquinolone in three steps from commercially available 2-vinylaniline in 44% overall yield. Also 3-fluorocoumarin and 3-fluorochromene were prepared from ovinylphenol, and 3-fluoro-benzoxepine was available from o-allylphenol.
A one-pot, three-component synthesis of thiazolidine-2-thiones
Ziyaei-Halimehjani, Azim,Marjani, Katayoun,Ashouri, Akram
body text, p. 3490 - 3492 (2012/08/27)
An efficient method for the synthesis of thiazolidine-2-thiones is described via regiospecific iodocyclization of an allyl amine, carbon disulfide, and iodine. Dehydrohalogenation of the iodo-derivatives gives thiazole-2(3H)-thiones. In addition, nucleoph
Coupling of 1-alkyl-2-(bromomethyl)aziridines with lithium dialkylcuprates towards 1,2-dialkylaziridines
D'Hooghe, Matthias,Rottiers, Mario,Jolie, Robrecht,De Kimpe, Norbert
, p. 931 - 934 (2007/10/03)
The reactivity of 1-alkyl-2-(bromomethyl)aziridines with respect to lithium dialkylcuprates (Gilman reagents) has been evaluated for the first time, pointing to the conclusion that these substrates can be applied successfully as synthetic equivalents for
Electron transfer induced ring opening of 2-(bromomethyl)aziridines by magnesium in methanol
Tehrani, Kourosch Abbaspour,NguyenVan, Tuyen,Karikomi, Michinori,Rottiers, Mario,De Kimpe, Norbert
, p. 7145 - 7152 (2007/10/03)
Magnesium metal in methanol was used as a simple electron transfer induced ring-opening reagent of 2-(bromomethyl)aziridines to afford allylamines derivatives in 70-90% yield.
Sonochemical Cleavage of 2-(Bromomethyl)aziridines by a Zinc-Copper Couple
Kimpe, Norbert De,Jolie, Rob,Smaele, Dirk De
, p. 1221 - 1222 (2007/10/02)
1-Alkyl- and 1-arylmethyl-2-(bromomethyl)aziridines are readily cleaved by the sonochemical zinc-copper couple in aqueous methanol at room temp. to afford allylamines.
