Pd-Catalyzed Intramolecular Heck Reaction, C(sp2)–H Activation, 1,4-Pd Migration, and Aminopalladation: Chemoselective Synthesis of Dihydroindeno[1,2,3-kl]acridines and 3-Arylindoles

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• 作者：Zheng-Yang Gu ; Cheng-Guo Liu ; Shun-Yi Wang ; Shun-Jun Ji
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：May 20, 2016
• 年：2016
• 卷：18
• 期：10
• 页码：2379-2382
• 全文大小：358K
• 年卷期：0
• ISSN：1523-7052

文摘

Palladium-catalyzed intramolecular Heck reaction and aminopalladation of N-(2-(1-phenylvinyl)phenyl)aniline for the efficient synthesis of dihydroindeno[1,2,3-kl]acridines and 3-arylindoles via tuning of the phosphine ligands and solvents under two optimized conditions are reported. The reaction follows a 1,4-Pd migration, aminopalladation, C(sp²)–H activation, as well as five- and six-membered-ring fusion to form different products. The dihydroindeno[1,2,3-kl]acridine derivatives showed higher triplet energy (E_T) levels than common blue phosphorescent dopant and may serve as good host candidates for blue triplet emitters.