Facile Synthesis of Dibenzotetracenedione Derivatives by Rhodium‐Catalyzed [2+2+2] Cycloaddition/Spontaneous Aromatization. Issue 10 (17th January 2019)

• Record Type: Journal Article
• Authors: Aida, Yukimasa; Shibata, Yu; Tanaka, Ken
• Is Part Of: Chemistry, an Asian journal. Volume 14:Issue 10(2019)
• Page Start: 1823
• Page End: 1829
• Publication Date: 2019-01-17
• Subjects: cycloaddition -- dibenzotetracenediones -- homogeneous catalysis -- rhodium -- synthesis design; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/asia.201801670
• Languages: English
• ISSNs: 1861-4728

Abstract

Abstract: It has been established that a cationic rhodium(I)/SEGPHOS complex catalyzes the [2+2+2] cycloaddition of biphenyl‐linked 1, 7‐diynes with 1, 4‐naphthoquinone and anthracene‐1, 4‐dione. Conveniently, spontaneous aromatization proceeded upon removal of the rhodium complex by passing the reaction mixture through an alumina column, to give the corresponding dibenzotetracenediones and dibenzopentacenediones, respectively, in good yields. The obtained dibenzotetracenedione could be readily transformed into the corresponding dibenzotetracene in good yield. This dibenzotetracene showed blue fluorescence with a good quantum yield, which was significantly higher than those of tetracene, tetrabenzotetracene, and hexabenzotetracene. Abstract : Running rings round rhodium : A cationic rhodium(I)/SEGPHOS complex catalyzes the [2+2+2] cycloaddition of biphenyl‐linked 1, 7‐diynes with 1, 4‐naphthoquinone and anthracene‐1, 4‐dione (see scheme). Conveniently, spontaneous aromatization proceeds upon removal of the rhodium complex by passing the reaction mixture through an alumina column to give the corresponding dibenzotetracenediones and dibenzopentacenediones, respectively, in good yields.