- Nickel(II) Catalyzed Hydroboration: A Route to Selective Reduction of Aldehydes and N-Allylimines
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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.
- Hossain, Istiak,Schmidt, Joseph A. R.
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p. 1877 - 1884
(2020/05/25)
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- FLUORINATED 2-AMINO-4-(SUBSTITUTED AMINO)PHENYL CARBAMATE DERIVATIVES
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The application relates to 2-amino-4-(substituted amino)phenyl carbamate derivatives, or pharmaceutically acceptable salts or solvates thereof, as KCNQ2/3 potassium channel modulators, and methods of their uses.
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Paragraph 0334
(2018/01/14)
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- Selective hydrosilylation of N-allylimines using a (3-iminophosphine)palladium precatalyst
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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
- Tafazolian, Hosein,Schmidt, Joseph A.R.
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p. 685 - 689
(2016/02/18)
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- Ring-closing metathesis of vinyl fluorides towards α-fluorinated α,β-unsaturated lactams and lactones
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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.
- Marhold, Michael,Stillig, Christian,Fr?hlich, Roland,Haufe, Günter
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supporting information
p. 5777 - 5785
(2014/10/15)
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- Structure and property based design, synthesis and biological evaluation of γ-lactam based HDAC inhibitors: Part II
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Histone deacetylases (HDACs) are involved in post-translational modification and epi-genetic expression, and have been the intriguing targets for treatment of cancer. In previous study, we reported synthesis and the biological preliminary results of γ-lactam based HDAC inhibitors. Based on the previous results, smaller γ-lactam core HDAC inhibitors are more active than the corresponding series of larger δ-lactam based analogues and the hydrophobic and bulky cap groups are required for better potency which decreased microsomal stability. Thus, γ-lactam analogues with methoxy, trifluoromethyl groups of ortho-, meta-, para-positions of cap group were prepared and evaluated their biological potency. Among them, trifluoromethyl analogues, which have larger lipophilicity, showed better HDAC inhibitory activity than other analogues. In overall, lipophilicity leads to increase hydrophobic interaction between surface of HDAC active site and HDAC inhibitor, improves HDAC inhibitory activity.
- Lee, Chulho,Choi, Eunhyun,Cho, Misun,Lee, Boah,Oh, Soo Jin,Park, Song-Kyu,Lee, Kiho,Kim, Hwan Mook,Han, Gyoonhee
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scheme or table
p. 4189 - 4192
(2012/07/03)
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