钯催化C3-对称9-芳基吖啶类衍生物的合成
Palladium-Catalyzed Syntheses of C3-Symmetric 9-Aryl Acridine Derivatives
Received date: 2017-07-06
Revised date: 2017-09-23
Online published: 2017-10-11
以均三溴苯和邻氨基苯甲酸甲酯为原料，经Buchwald-Hartwig反应、酯基水解和三氯氧磷关环三步合成关键中间体6，12，18-三氯二苯并[b，j]喹啉[2，3-f][1，7]菲罗啉，最后在新型催化剂Pd-132催化下进行Suzuki偶联，高效合成了14个具有代表性的C3-对称-9-芳基吖啶类衍生物.该方法具有催化剂用量低（0.1 mol%，平均到每一个位点仅为0.03 mol%），原料易得，便于推广的特点.
关键词： Buchwald-Hartwig反应; 吖啶; Pd-132; Suzuki偶联
董坤 , 李秋云 , 安康 , 马俊逸 , 白中胜 , 刘乾才 . 钯催化C3-对称9-芳基吖啶类衍生物的合成[J]. 有机化学, 2018 , 38(2) : 416 -424 . DOI: 10.6023/cjoc201707007
A multiple synthetic strategy is employed to furnish the synthesis of 6, 12, 18-triaryldibenzo[b, j]quinoline[2, 3-f] [1, 7]phenanthroline. The key intermediate 6, 12, 18-trichlorobenzotriquinoline was prepared by Buchwald-Hartwig reaction of 1, 3, 5-tribromobenzene with methyl anthranilate, followed by hydrolysis and POCl3-promoted ring closure reaction. The palladium-catalyzed Suzuki coupling was carried out with a novel catalyst Pd-132 to form fourteen C3-symmetric 9-aryl acridine derivatives. The reactions can be performed at low catalyst loading (0.1 mol%, ca. 0.03 mol% per site).
Key words： Buchwald-Hartwig reaction; acridine; Pd-132; Suzuki coupling
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