105336-48-9Relevant academic research and scientific papers
Redox-Neutral β-C(sp3)-H Functionalization of Cyclic Amines via Intermolecular Hydride Transfer
Zhou, Lan,Shen, Yao-Bin,An, Xiao-De,Li, Xian-Jiang,Li, Shuai-Shuai,Liu, Qing,Xiao, Jian
, p. 8543 - 8547 (2019)
Herein, we report the first redox-neutral and transition-metal-free β-C(sp3)-H functionalization of cyclic amines via a consecutive intermolecular hydride transfer process. A series of N-aryl pyrrolidines and N-aryl 1,2,3,4-tetrahydropyridines decorated with CF3 and carboxylic ester functionalities are directly accessed in good yields from pyrrolidines and piperidines. This work pushes forward the application of the intermolecular hydride transfer strategy in one-step assembly of molecular complexity.
Platinum/scandium-cocatalyzed cascade cyclization and ring-opening reaction of tertiary amines with substituted salicylaldehydes to synthesize 3-(aminoalkyl)coumarins
Xia, Xiao-Feng,Shu, Xing-Zhong,Ji, Ke-Gong,Shaukat, Ali,Liu, Xue-Yuan,Liang, Yong-Min
supporting information; experimental part, p. 342 - 345 (2011/03/19)
The synthesis of 3-(aminoalkyl)coumarins starting with a platinum/scandium-cocatalyzed oxidative dehydrogenation of α,β- C(sp3)-H bonds of tertiary amines in the presence of ambient oxygen followed by reactions with substituted salicylaldehydes is revealed. The in situ formed enamines reacted with various salicylaldehydes, which resulted in the development of a one-pot synthetic protocol involving aldol reaction, cyclization, and then ring-opening.
Platinum-catalyzed michael addition and cyclization of tertiary amines with nitroolefins by dehydrogenation of α,β-sp3 C-H bonds
Xia, Xiao-Feng,Shu, Xing-Zhong,Ji, Ke-Gong,Yang, Yan-Fang,Shaukat, Ali,Liu, Xue-Yuan,Liang, Yong-Min
supporting information; experimental part, p. 2893 - 2902 (2010/07/09)
A mild platinum-catalyzed oxidative dehydrogenation of α,β- C(sp3)-H bonds of tertiary amines in the presence of ambient oxygen is revealed, and the in situ formed enamines subsequently reacting with various nitroolefins resulted in the development of two one-pot synthetic protocols involving Michael addition-elimination and Michael addition-cyclization. By using different functionalized nitroolefins compatible with the current oxidative conditions, two types of structurally divergent products, trisubstituted enamines and chromano[2,3-b]piperidines, could be expediently accessed, respectively.
Selective functionalization of sp3 C - H bonds adjacent to nitrogen using (diacetoxyiodo)benzene (DIB)
Shu, Xing-Zhong,Xia, Xiao-Feng,Yang, Yan-Fang,Ji, Ke-Gong,Liu, Xue-Yuan,Liang, Yong-Min
supporting information; experimental part, p. 7464 - 7469 (2010/01/06)
(Chemical Equation Presented) A PhI(OAc)2 mediated selective functionalization of sp3C - H bonds adjacent to a nitrogen atom has been reported. When piperidine derivates were used, direct diacetoxylation of α and β sp3 C - H adjacent to a nitrogen atom were observed to afford various cis-2,3-diacetoxylated piperidines. On the other hand, tetrahydroisoquinoline derivatives gave various α-C - H functionalized products in the presence of PhI(OAc)2. Nitroalkanes, dialkyl malonates, and β-keto ester are active participants in this coupling reaction. Meanwhile, α-amino nitriles can also be obtained by oxidative coupling of amineswithmalononitrile. 2009 American Chemical Society.
Reaction of 4-Bromo-1,2-dimethylbenzene with Various Nucleophiles via Aryne Reaction
Biehl, Edward R.,Razzuk, Aziz,Jovanovic, Misa V.,Khanapure, Subhash P.
, p. 5157 - 5160 (2007/10/02)
4-Bromo-1,2-dimethylbenzene (4a) reacts with a variety of amines, mercaptans, and nitriles under aryne-forming conditions to yield predominantly 4-substituted 1,2-dimethylbenzenes and minor quantities of 3-substituted 1,2-dimethylbenzenes.The product distributions from these reactions are heavily in favor of the 4-substituted isomer since it is formed exclusively from the symmetric 4,5-dimethylbenzyne intermediate (6) and partly from the unsymmetric 3,4-dimethylbenzyne intermediate (5).
