Palladium-Catalyzed Synthesis of Isocoumarins and Phthalides via tert-Butyl Isocyanide Insertion

• Published in: Journal of organic chemistry Vol. 77; no. 22; pp. 10321 - 10328
• Main Authors: Fei, Xiang-Dong, Ge, Zhi-Yuan, Tang, Ting, Zhu, Yong-Ming, Ji, Shun-Jun
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society 16-11-2012
• Subjects: Benzofurans - chemical synthesis; Benzofurans - chemistry; Catalysis; Chemistry; Cyclization; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives; Hydrolysis; Isocoumarins - chemical synthesis; Isocoumarins - chemistry; Lactones - chemistry; Molecular Structure; Nitriles - chemistry; Organic chemistry; Palladium; Preparations and properties; Hydrolysis; Catalytic reaction; Cyclization; Chemical compound library; Palladium complex; Lactone; Oxygen heterocycle; Chemical synthesis; Isocoumarin derivative
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo302004u

A novel and highly efficient strategy for the synthesis of isocoumarins and phthalides through a palladium(0)-catalyzed reaction incorporating tert-butyl isocyanide has been developed. This process, providing one of the simplest methods for the synthesis of this class of valuable lactones, involves two steps including cyclization reaction and simple acid hydrolysis. The methodology is tolerant of a wide range of substrates and applicable to library synthesis.