Bede Fanni, Takács Attila, Kollár László, Pongrácz Péter
Department of General and Inorganic Chemistry, University of Pécs, Ifjúság u. 6., H-7624 Pécs, Hungary.
HUN-REN-PTE Research Group for Selective Chemical Syntheses, Ifjúság u. 6., H-7624 Pécs, Hungary.
Molecules. 2024 Nov 27;29(23):5620. doi: 10.3390/molecules29235620.
Palladium-catalyzed carbonylation reactions of -phenylene dihalides were studied using aminoethanols as heterobifunctional ,-nucleophiles. The activity of aryl-iodide and -bromide as well as the chemoselective transformation of amine and hydroxyl functionalities were studied systematically under carbonylation conditions. Aminocarbonylation can be selectively realized under optimized conditions, enabling the formation of amide alcohols, and the challenging alkoxycarbonylation can also be proved feasible, enabling amide-ester production. Intramolecular double carbonylation reaction can be achieved using 1,2-diiodobenzene and amino alcohols featuring secondary amine groups, giving oxazocine derivatives. Useful reaction scope with various amino alcohols was performed with good isolated yields of the targeted compounds. Intramolecular C-O coupling of amide alcohols possessing bromo substituent in adjacent position is also demonstrated as a potential next step in benzoxazepine heterocycle formation.
使用氨基乙醇作为异双官能团的α，ω-亲核试剂，研究了对苯二卤化物的钯催化羰基化反应。在羰基化条件下，系统地研究了芳基碘化物和芳基溴化物的活性以及胺和羟基官能团的化学选择性转化。在优化条件下可以选择性地实现氨羰基化反应，从而形成酰胺醇，同时也证明了具有挑战性的烷氧基羰基化反应是可行的，能够生成酰胺酯。使用1,2-二碘苯和具有仲胺基团的氨基醇可以实现分子内双羰基化反应，得到恶唑嗪衍生物。使用各种氨基醇进行了有用的反应范围研究，目标化合物的分离产率良好。还证明了在相邻位置具有溴取代基的酰胺醇的分子内C-O偶联是苯并恶唑嗪杂环形成的潜在下一步反应。
