Quinoline derivatives transfer hydrogenation

Cascade Transfer Hydrogenation of Quinoline and Pyridine Derivatives... 

Transfer hydrogenation of quinolines has also been studied using a 3,3-linked dimeric BINOL derivative 2 in which both subunits are phosphorylated. ... 

Recently, an interesting principle of formation for 2-substituted quinoline derivatives was realized in the Pd-catalysed transfer hydrogenation/heterocyclization of (o-aminophenyl)ynones 60 in the presence of tertiary amin/formic acid to give 61 [96] ... 

The transfer hydrogenation of 3-substituted quinolines was also studied, with the particularity that the stereogenic center was generated in this case during the conjugate addition step (Scheme 4.60). ° The reaction needed for a more sterically demanding catalyst such as partially hydrogenated derivative 60f and, in addition, the nature of the Hantzsch ester required further optimization in order to achieve the best enantioselectivities, which still remained in values around 80% ee. In this case, the scope of the reaction was limited to the use of quinolines with aromatic or heteroaromatic substituents at the 3-position. 

The transition metal, organo-catalysed enantioselective hydrogenation and chiral phosphoric acid-catalysed transfer hydrogenation of aromatic and heteroaromatic compounds such as quinoline, indole, and pyrrole derivatives were featured in Science of Synthesis, Stereoselective Synthesis (2011). ... 

The first enantioselective synthesis of 4-aza-podophyllotoxin derivatives (211) has been achieved using a chiral biphenyl phosphoric acid catalyst (212) through a partial transfer hydrogenation of lactone-fused quinolines (210) (Scheme 56)7 ... 

Scheme 11.14 Asymmetric transfer hydrogenation of quinoline derivatives.

In some ylides photolytic conditions were necessary for their transylidation [30]. The conversion of iodonium ylides into a-halogeno derivatives of the parent carbonyl compound (or other precursor) with hydrogen halides is normally effected directly, without isolation of their iodonium salts. A similar reaction with halogens leads to the formation of a,a-bis halogenated products [31]. The reaction of pyridines with the non-isolable PhI=C(CN)2 is of interest, since it permits the ready transfer of the C(CN)2 functionality to the nitrogen of pyridine, quinoline, etc. the yields here were generally moderate but in some cases the products could not be obtained using other dicyanocarbene precursors [32],... 

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