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The Palladium-Catalyzed Heteroarylation of Adamantylalkyl Amines with Dihalogenopyridines: Scope and Limitations
Synthesis ( IF 2.6 ) Pub Date : 2017-08-07 , DOI: 10.1055/s-0036-1590860
Irina Beletskaya 1, 2 , Anton Abel 1 , Alexei Averin 1, 2 , Alexei Buryak 2 , Evgenii Savelyev 3 , Boris Orlinson 3 , Ivan Novakov 3
Affiliation  

Abstract

Palladium-catalyzed heteroarylation of adamantylalkyl amines characterized by different steric hindrances at the amino group was carried out using 2,3-, 2,5-, 2,6-, and 3,5-dihalogenopyridines. The dependence of the results of the coupling on the nature of the halogen atoms (bromine, chlorine), their position in the pyridine ring, and on the structure of adamantylalkyl amines was investigated. The application of dichloropyridines or bromochloropyridines was shown to be advantageous over the use dibromopyridines in many cases. Selective substitution of bromine atom in positions 3 and 5 in the presence of chlorine atom in position 2 of the pyridine ring was observed. The possibility of N,N-diheteroarylation of adamantane-containing amines with 2,5-dihalogenopyridines was shown, and diamination of 2,6- and 3,5-dihalogenopyridines was demonstrated.

Palladium-catalyzed heteroarylation of adamantylalkyl amines characterized by different steric hindrances at the amino group was carried out using 2,3-, 2,5-, 2,6-, and 3,5-dihalogenopyridines. The dependence of the results of the coupling on the nature of the halogen atoms (bromine, chlorine), their position in the pyridine ring, and on the structure of adamantylalkyl amines was investigated. The application of dichloropyridines or bromochloropyridines was shown to be advantageous over the use dibromopyridines in many cases. Selective substitution of bromine atom in positions 3 and 5 in the presence of chlorine atom in position 2 of the pyridine ring was observed. The possibility of N,N-diheteroarylation of adamantane-containing amines with 2,5-dihalogenopyridines was shown, and diamination of 2,6- and 3,5-dihalogenopyridines was demonstrated.



中文翻译:

金刚烷基烷基胺与二卤代吡啶的钯催化杂芳基化:范围和局限性

摘要

使用2,3-,2,5-,2,6-和3,5-二卤代吡啶进行钯催化的金刚烷基烷基胺的杂芳基化,其特征在于氨基上的空间位阻不同。研究了偶联结果对卤素原子(溴,氯)的性质,它们在吡啶环中的位置以及金刚烷基烷基胺的结构的依赖性。在许多情况下,使用二氯吡啶或溴氯吡啶显示出优于使用二溴吡啶的优势。在吡啶环的2位上存在氯原子的情况下,观察到3和5位上的溴原子的选择性取代。NN的可能性显示了含金刚烷胺与2,5-二卤代吡啶的二异芳基化,并证明了2,6-和3,5-二卤代吡啶的苯胺化。

使用2,3-,2,5-,2,6-和3,5-二卤代吡啶进行钯催化的金刚烷基烷基胺的杂芳基化,其特征在于氨基上的空间位阻不同。研究了偶联结果对卤素原子(溴,氯)的性质,它们在吡啶环中的位置以及金刚烷基烷基胺的结构的依赖性。在许多情况下,使用二氯吡啶或溴氯吡啶显示出优于使用二溴吡啶的优势。在吡啶环的2位上存在氯原子的情况下,观察到3和5位上的溴原子的选择性取代。NN的可能性显示了含金刚烷胺与2,5-二卤代吡啶的二异芳基化,并证明了2,6-和3,5-二卤代吡啶的苯胺化。

更新日期:2017-08-07
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