Palladium‐Catalyzed Carbonylation of ortho‐Alkenyl Iodobenzenes for the Construction of 3‐Arylindenones

• Published in: Chinese journal of chemistry Vol. 43; no. 10; pp. 1135 - 1140
• Main Authors: Qian, Minxiu, Yao, Lingyun, Li, Zhi, Shao, Xusheng, Wang, Quannan, Deng, Wei‐Ping
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY‐VCH Verlag GmbH & Co. KGaA 15.05.2025; Wiley; Wiley Subscription Services, Inc
• Subjects: C1 building blocks; Carbon monoxide; Carbonylation; Carbonyls; Chemistry; Chemistry, Multidisciplinary; Functional groups; Indenones; Methodology and reactions; Palladium; Pd‐catalyzed; Physical Sciences; Science & Technology; RHODIUM; ANNULATION; Pd-catalyzed; ALKYNES; C-H ACTIVATION; Carbonylation; 1,4-MIGRATION; C1 building blocks; Methodology and reactions; CHEMISTRY; Indenones; SUBSTITUTED NAPHTHALENES; Carbon monoxide; BOND; CYCLIZATION
• ISSN: 1001-604X; 1614-7065
• DOI: 10.1002/cjoc.202401269

Comprehensive Summary We developed a novel Pd‐catalyzed carbonylation of ortho‐alkenyl iodobenzenes with CO, affording a diverse array of 3‐arylindenones in good to excellent yields (up to 94% yield). This methodology exhibits broad substrate scope and good functional group compatibility. The synthetic utility was demonstrated by a gram‐scale reaction, diverse product derivatizations, and the preparation of an intermediate for a PPARγ agonist. We developed a novel Pd‐catalyzed carbonylation of ortho‐alkenyl iodobenzenes with CO, affording a diverse array of 3‐arylindenones in good to excellent yields (up to 94% yield). This methodology exhibits broad substrate scope and good functional group compatibility. The synthetic utility was demonstrated by a gram‐scale reaction, diverse product derivatizations, and the preparation of an intermediate for a PPARγ agonist.