Rhodium(I)‐Catalyzed Carboacylation/Aromatization Cascade Initiated by Regioselective C−C Activation of Benzocyclobutenones. (12th February 2018)

• Record Type: Journal Article
• Authors: Sun, Tianwen; Zhang, Yuna; Qiu, Bo; Wang, Yafei; Qin, Yuting; Dong, Guangbin; Xu, Tao
• Is Part Of: Angewandte Chemie. Volume 130:Number 11(2018)
• Page Start: 2909
• Page End: 2913
• Publication Date: 2018-02-12
• Subjects: Carboacylierung -- C-C-Aktivierung -- Reaktionsmechanismen -- Rhodium -- Totalsynthesen; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201713179
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: Described here is the first example of a rhodium‐catalyzed carboacylation/aromatization cascade of a C=O bond by C−C activation. In this transformation, a reactive rhodaindanone complex is regioselectively generated and adds across a C=O bond with subsequent elimination, thus providing a unique strategy to access a multisubstituted benzofuran scaffold. A diverse range of benzofuran analogues were obtained in good yields. Mechanistic studies show a tricyclic lactone was a viable intermediate. Application of this methodology to the total synthesis of C13‐deOH‐viniferifuran and C13‐deOH‐diptoindonesin G was achieved.