Palladium-catalyzed cascade carbonylative annulation between alkene-tethered aryl iodides and carbon monoxide

• Published in: Chemical communications (Cambridge, England) Vol. 57; no. 57; pp. 723 - 726
• Main Authors: Zhang, Yong, Sun, Ya-Kui, Chang, Ya-Ping, Shao, Hui, Zhao, Yu-Ming
• Format: Journal Article
• Language: English
• Published: CAMBRIDGE Royal Soc Chemistry 21.07.2021; Royal Society of Chemistry
• Subjects: Acylation; Aromatic compounds; Carbon monoxide; Carbonyls; chemical communication; Chemical reactions; Chemical synthesis; Chemistry; Chemistry, Multidisciplinary; Iodides; methodology; Palladium; Physical Sciences; Science & Technology; Substitutes; DOMINO REACTION; ALKYLATION; SPIROANNULATION; SPIROCYCLIZATION; C-H ACTIVATION; ECONOMY; CYCLIZATION
• ISSN: 1359-7345; 1364-548X; 1364-548X
• DOI: 10.1039/d1cc02217b

Rapid construction of molecules bearing all-substituted quaternary stereocenters represents a highly significant but challenging task in organic synthesis. Herein, we report a novel palladium-catalyzed cascade between alkene-tethered aryl iodides and carbon monoxide, which has resulted in a practical and powerful method for the synthesis of complex polycyclic molecules containing aryl-substituted quaternary stereocenters. Mechanistic studies suggested that the reaction proceeded via a Heck-type carbonylative cyclization, followed by a ketene-involved Friedel-Crafts acylation. A novel Pd-catalyzed carbonylative cascade of alkene-tethered aryl iodides has been developed. Mechanistic studies suggested the reaction proceeded via a Heck-type carbonylative cyclization, followed by a ketene-involved Friedel-Crafts acylation.