Transition‐Metal‐Free Synthesis of Homo‐ and Hetero‐1, 2, 4‐Triaryl Benzenes by an Unexpected Base‐Promoted Dearylative Pathway. Issue 27 (9th April 2016)

• Record Type: Journal Article
• Authors: Rehan, Mohammad; Maity, Sanjay; Morya, Lalit Kumar; Pal, Kaushik; Ghorai, Prasanta
• Is Part Of: Angewandte Chemie international edition. Volume 55:Issue 27(2016)
• Page Start: 7728
• Page End: 7732
• Publication Date: 2016-04-09
• Subjects: arenes -- cyclizations -- materials science -- regioselectivity -- synthetic methods; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201511424
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: An unprecedented approach for the synthesis of homo‐ and hetero‐1, 2, 4‐triaryl benzenes has been developed using a simple base‐mediated reaction of either α‐aryl cinnamyl alcohols or α, γ‐di‐aryl propanones. The salient feature of this strategy involves the sequential hydride transfer, regiospecific condensation, regiospecific dearylation, and aromatization under metal‐free reaction conditions. The synthesis of unsymmetrically substituted triphenylenes by oxidative coupling of the synthesized 1, 2, 4‐triaryl benzenes has also been demonstrated. Abstract : Rings on rings : An unprecedented approach for the synthesis of homo‐ and hetero‐1, 2, 4‐triaryl benzenes has been developed by a simple KOH/DMSO‐mediated reaction of either α‐aryl cinnamyl alcohols or α, γ‐di‐aryl propanones. The salient feature of this strategy involves sequential hydride transfer, regiospecific condensation, regiospecific dearylation, and aromatization under metal‐free reaction conditions. DMSO=dimethylsulfoxide.