645-59-0Relevant articles and documents
A Study of the Sodium Borohydride Reduction of α,β-Acetylenic vs α,β-Olefinic Nitriles
Kulp, Stuart S.,Szarko, Richard
, p. 5573 - 5574 (1988)
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Enantioselective hydrogenation of diaryl-substituted α,β-unsaturated nitriles
Wabnitz, Tobias C.,Rizzo, Simona,G?tte, Carsten,Buschauer, Armin,Benincori, Tiziana,Reiser, Oliver
, p. 3733 - 3736 (2006)
α,β-Unsaturated nitriles can be hydrogenated with enantioselectivities up to 88% ee using chiral ruthenium-diphenylphosphino bisaryl and bisheteroaryl complexes such as ruthenium(II)-BINAP and ruthenium(II)-BINP. Mechanistic investigations indicate that conversion is accelerated by electron-rich ligands and that an additional coordinative group needs be present in order to promote conversion. The chiral products are useful building blocks for the synthesis of histamine H2 agonists of the arpromidine type.
Palladium-catalyzed synthesis of nitriles from N-phthaloyl hydrazones
Ano, Yusuke,Chatani, Naoto,Higashino, Masaya,Yamada, Yuki
supporting information, p. 3799 - 3802 (2022/04/07)
The Pd-catalyzed transformation of N-phthaloyl hydrazones into nitriles involving the cleavage of an N-N bond is reported. The use of N-heterocyclic carbene as a ligand is essential for the success of the reaction. N-Phthaloyl hydrazones prepared from aromatic aldehydes or cyclobutanones are applicable to this transformation, which gives aryl or alkenyl nitriles, respectively.
Reduction of Electron-Deficient Alkenes Enabled by a Photoinduced Hydrogen Atom Transfer
Larionova, Natalia A.,Ondozabal, Jun Miyatake,Cambeiro, Xacobe C.
supporting information, p. 558 - 564 (2020/12/07)
Direct hydrogen atom transfer from a photoredox-generated Hantzsch ester radical cation to electron-deficient alkenes has enabled the development of an efficient formal hydrogenation under mild, operationally simple conditions. The HAT-driven mechanism is supported by experimental and computational studies. The reaction is applied to a variety of cinnamate derivatives and related structures, irrespective of the presence of electron-donating or electron-withdrawing substituents in the aromatic ring and with good functional group compatibility. (Figure presented.).