33098-80-5Relevant academic research and scientific papers
A Four-Step Synthesis of (±)-γ-Lycorane via Pd0-Catalyzed Double C(sp2)-H/C(sp3)-H Arylation
Rocaboy, Ronan,Dailler, David,Baudoin, Olivier
supporting information, p. 772 - 775 (2018/02/09)
An expedient synthesis of lycorine alkaloids is reported using a palladium(0)-catalyzed double C-X/C-H arylation as the key step. The selectivity of this reaction was controlled through the judicious choice of the two halogen atoms, and its generality was
Mild C - H halogenation of anilides and the isolation of an unusual palladium(I)-palladium(II) species
Bedford, Robin B.,Haddow, Mairi F.,Mitchell, Charlotte J.,Webster, Ruth L.
supporting information; experimental part, p. 5524 - 5527 (2011/07/31)
Reducing the load: A facile palladium-catalyzed ortho-selective bromination and chlorination of anilides occurs under aerobic conditions at room temperature when N-halosuccinimides (NXS) are used in the presence of p-toluenesulfonic acid (PTSA). The orthopalladated PTSA complex is not only catalytically competent but also undergoes a reductive process to yield an unusual PdI-PdII tetramer (see structure; Pdgreen, Ored, Syellow, Cgray). Copyright
0-amine-assisted cannizzaro reaction of glyoxal with new 2,6-diaminoanilines
Irie, Yuhki,Koga, Yuji,Matsumoto, Taisuke,Matsubara, Kouki
body text, p. 2243 - 2250 (2009/08/09)
The preparation of several new o-amine-substituted anilines was achieved according to a new bifunctional molecular design, and their reactions with glyoxal were conducted. Can- nizzaro reactions of glyoxal proceeded using specifically designed anilines, such as 2,6-dipyrrolidinyl-, 2,6-dipiperidinyl-, 2,6-dimorpholinyl-, and 2-pyrrolidinyl-aniline, which are new and can easily be synthesized by substitution of halogen-substituted nitrobenzene with amines and subsequent reduction with hydrogen, to form a-hydroxy acetamide and a-amino acetamide derivatives, as a result of the Cannizzaro reaction. In comparison with the reaction of glyoxal with p- pyrrolidinylaniline to form a common diimine product, the reaction with o-pyrrolidinylaniline leads only to a-hydroxy amides, strongly suggesting that the abnormal Cannizzaro reactions are attributed to the existence of basic nitrogen atoms at the o-positions, which suppress diimine formation and assist the generation of acetamides.
