Acid-Catalyzed Domino Reactions of Tetraarylbut-2-yne-1,4-diols. Synthesis of Conjugated Indenes and Inden-2-ones

作者：Sousa Ceu M; Berthet Jerome; Delbaere Stephanie; Coelho Paulo J^*

来源：Journal of Organic Chemistry, 2014, 79(12): 5781-5786.

DOI：10.1021/jo500907z

The reaction of tetraarylbut-2-yne-1,4-diols with electron-rich aromatic compounds at room temperature, under p-TsOH catalysis, affords substituted polycyclic aromatic indene derivatives through a domino reaction involving the formation of a cationic allenylium intermediate. This species can undergo a series of competitive intra-molecular cascade reactions, leading to a conjugated inden-2-one. This simple method allows the efficient synthesis of substituted indenes and inden-2-ones, in two steps, from aromatic ketones.

• 出版日期2014-6-20