Rhodium(I)‐Catalyzed Carboacylation/Aromatization Cascade Initiated by Regioselective C−C Activation of Benzocyclobutenones. Issue 11 (13th 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 international edition. Volume 57:Issue 11(2018)
• Page Start: 2859
• Page End: 2863
• Publication Date: 2018-02-13
• Subjects: carboacylation -- C−C activation -- reaction mechanisms -- rhodium -- total synthesis; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201713179
• Languages: English
• ISSNs: 1433-7851

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. Abstract : In a rhodium‐catalyzed carboacylation/aromatization cascade of a C=O bond by C−C activation, a reactive rhodaindanone complex is regioselectively generated, adds across the C=O bond, and undergoes elimination, thus providing access to a multisubstituted benzofuran scaffold. A diverse range of benzofuran analogues were obtained in good yields. This methodology was used in the total syntheses of C13‐deOH‐viniferifuran and C13‐deOH‐diptoindonesin G.