- Intramolecular Pd-catalyzed reductive amination of enolizable sp3-C-H bonds
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A palladium-catalyzed reductive cyclization of nitroarenes has been designed to construct sp3-C-NHAr bonds from sp3-C-H bonds by using an enolizable nucleophile to intercept a nitrosoarene intermediate. Exposure of ortho-substituted nitroarenes to 5 mol ?% of Pd(OAc)2 and 10 mol ?% of phenanthroline under 2 atm of CO constructs partially saturated 5-, 6-, or 7-membered N-heterocycles using α-pyridyl carboxylates, malonates, 1,3-dimethylbarbituric acid, 1,3-diones, or difurans as the nucleophile.
- Ford, Russell L.,Alt, Isabel,Jana, Navendu,Driver, Tom G.
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supporting information
p. 8827 - 8831
(2019/10/28)
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- Rotational features of carbon-nitrogen bonds in N-aryl maleimides. Atroposelective reactions of o-tert-butylphenylmaleimides
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Atroposelective addition and cycloaddition reactions of N-2- (tertbutylphenyl)- and N-2,5 (di-tert-butylphenyl)maleimide and a substituted derivative have been studied. Good to excellent stereoselectivities are generally observed, and high rotation barriers (about 29 kcal/mol) prevent the products from inter, converting. Crystal structures of the precursors and products support a straightforward model where reactants attack trans to the o-tert butyl group.
- Curran, Dennis P.,Geib, Steven,DeMello, Nicholas
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p. 5681 - 5704
(2007/10/03)
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- Synthesis and Characterization of 2H-, 3H- and 4H-Azepine: The First Observation of the Thermal Distribution Equilibrium of Azepines
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Demethoxycarbonylation of methyl 2,5-di-tert-butyl-1H-azepine-1-carboxylate using 1,8-diazabicycloundec-7-ene gives exclusively two isomers of 3H-azepine derivatives, while methyl 3,6-di-tert-butyl-1H-azepine-1-carboxylate gives a mixture of 2H-, 3H- and 4H-azepine derivatives under the same conditions because of a 1,5-hydrogen shift in the resulting triene system.
- Satake, Kyosuke,Okuda, Ryoichi,Hashimoto, Michiaki,Fujiwara, Yasushi,Watadani, Izumi,et al.
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p. 1154 - 1156
(2007/10/02)
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