One‐Pot Palladium‐Catalyzed Carbonylative Sonogashira Coupling using Carbon Dioxide as Carbonyl Source. Issue 12 (5th May 2021)

• Record Type: Journal Article
• Authors: Xiong, Wenfang; Wu, Bowen; Zhu, Baiyao; Tan, Xiaobin; Wang, Lu; Wu, Wanqing; Qi, Chaorong; Jiang, Huanfeng
• Is Part Of: ChemCatChem. Volume 13:Issue 12(2021)
• Page Start: 2843
• Page End: 2851
• Publication Date: 2021-05-05
• Subjects: Pd-catalyzed -- carbonylative Sonogashira -- carbon dioxide -- simple and safe operation; Catalysis -- Periodicals; 541.39505
• DOI: 10.1002/cctc.202100051
• Languages: English
• ISSNs: 1867-3880

Abstract

Abstract: Carbonylation coupling reaction has emerged as a powerful and versatile strategy for the construction of carbonyl‐containing compounds in modern synthetic chemistry over the past years. Carbon dioxide, a renewable one carbon molecule, has become one of the most attractive and promising alternative carbonyl sources due to its highly abundance, nontoxicity and stability in comparison with CO in recent years. However, in most cases, a two‐chamber technique was generally necessary to allow the CO‐producing and CO‐consuming processes to perform successfully because of the complexities and incompatibility of reaction conditions, when carbon dioxide was utilized as carbonyl source. Herein, a practical one‐pot protocol using carbon dioxide as the carbonyl source for the palladium‐catalyzed carbonylative Sonogashira coupling has been established, providing an expedient and practical route to a wide range of functionalized alkynones and indoxyls under mild reaction conditions. By finding a suitable catalytic system, the method allowed the CO‐generating and CO‐consuming processes to proceed in one pot, wherein carbon monoxide was generated in situ from the reduction of carbon dioxide in the absence of any fluoride reagents. Simple and safe operation, readily available substrates, good functional group tolerance and mild reaction conditions are the features of the method. Abstract : One‐pot synthesis : We report a practical one‐pot protocol using carbon dioxide as the carbonyl source for the palladium‐catalyzed carbonylative Sonogashira coupling, providing an efficient and practical route to a wide range of functionalized alkynones and indoxyls under mild reaction conditions.