1346451-17-9Relevant academic research and scientific papers
Method for activating C-H bond at site alpha of heteroatom under catalysis of Cu
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Paragraph 0139-0145; 0161-0165, (2021/08/07)
The invention relates to the technical field of organic synthesis, in particular to a method for activating a C-H bond at the site alpha of a heteroatom under the catalysis of Cu. The method provided by the invention comprises the steps that with copper as a catalyst and a fluorine reagent of an N-F bond as an oxidizing agent, the C-H bond at the site alpha of a heteroatom in a heterocyclic compound is oxidized and activated to obtain a hemiacetal or aminal structure; and the structure can be eliminated under the condition of acidity or in the presence of F so as to obtain an imine salt intermediate, and the imine salt intermediate reacts with a nucleophilic reagent to further activate the C-H bond at the alpha position of a heterocyclic ring. According to the activation method, various heterocyclic rings can be uniformly activated, and the activation method is simple to operate.
Diverse reactions of sulfonyl chlorides and cyclic imines
Liu, Jing,Hou, Shili,Xu, Jiaxi
experimental part, p. 2377 - 2391 (2012/04/04)
Although alkanesulfonyl chlorides react with linear imines to give rise to β-sultam derivatives, in this study, they were reacted with various cyclic imines, including 1-pyrroline, oxazoline, 5,6-dihydro-4H-oxazines and thiazines, 4,5-dihydro-3H-benzo[c]azepine, and 3,4-dihydroisoquinoline, to produce diverse products instead of β-sultam derivatives. The results indicate that alkanesulfonyl chlorides react with cyclic imines to generate N-alkanesulfonyl cyclic iminium ions, which are attacked by nucleophiles, such as water and chloride anion, in the reaction systems, affording addition products. The iminium intermediates cannot undergo a ring closure to form β-sultam derivatives. Arenesulfonyl chlorides showed similar behavior when they reacted with cyclic imines. The scope and limitation of the reaction between sulfonyl chlorides and imines were investigated. Copyright Taylor & Francis Group, LLC.
