Divergent Palladium‐Catalyzed Tandem Reaction of Cyanomethyl Benzoates with Arylboronic Acids: Synthesis of Oxazoles and Isocoumarins. Issue 9 (3rd April 2020)

• Record Type: Journal Article
• Authors: Dai, Ling; Yu, Shuling; Xiong, Wenzhang; Chen, Zhongyan; Xu, Tong; Shao, Yinlin; Chen, Jiuxi
• Is Part Of: Advanced synthesis & catalysis. Volume 362:Issue 9(2020)
• Page Start: 1893
• Page End: 1898
• Publication Date: 2020-04-03
• Subjects: palladium-catalyzed -- tandem reaction -- oxazoles -- isocoumarins -- nitriles; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.202000125
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: A palladium‐catalyzed tandem reaction of cyanomethyl benzoates with arylboronic acids has been achieved. Substitution at the 2‐position of cyanomethyl benzoates was found to be crucial for the selective synthesis of oxazoles and isocoumarins. Cyanomethyl benzoates afforded 2, 4‐diaryloxazoles as products, while 2‐benzoyl‐substituted cyanomethyl benzoates delivered 3‐benzoyl‐4‐aryl‐isocoumarins selectively. Furthermore, a possible mechanism for the selective reaction of cyanomethyl benzoates with arylboronic acids was discussed. Abstract :