AuCl3‐Catalyzed Ring‐Closing Carbonyl–Olefin Metathesis

• Published in: Chemistry : a European journal Vol. 26; no. 9; pp. 1941 - 1946
• Main Authors: Wang, Rui, Chen, Yi, Shu, Mao, Zhao, Wenwen, Tao, Maoling, Du, Chao, Fu, Xiaoya, Li, Ao, Lin, Zhihua
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 11.02.2020; Wiley Subscription Services, Inc
• Subjects: benzocarbocycles; Carbon; Carbonyl compounds; Carbonyls; Chemistry; Chemistry, Multidisciplinary; Decomposition reactions; gold catalysis; heterocycles; Metathesis; organic synthesis; Physical Sciences; Science & Technology; metathesis; heterocycles; organic synthesis; CARBOCATION; benzocarbocycles; CATALYZED OLEFINATION; STEREOSELECTIVE SYNTHESES; gold catalysis; ONE HUNDRED YEARS
• ISSN: 0947-6539; 1521-3765
• DOI: 10.1002/chem.201905199

Compared with the ripeness of olefin metathesis, exploration of the construction of carbon–carbon double bonds through the catalytic carbonyl–olefin metathesis reaction remains stagnant and has received scant attention. Herein, a highly efficient AuCl3‐catalyzed intramolecular ring‐closing carbonyl–olefin metathesis reaction is described. This method features easily accessible starting materials, simple operation, good functional‐group tolerance and short reaction times, and provides the target cyclopentenes, polycycles, benzocarbocycles, and N‐heterocycle derivatives in good to excellent yields. Heterocycles: AuCl3 efficiently catalyzed an intramolecular ring‐closing carbonyl–olefin metathesis reaction providing target cyclopentenes, phenanthrenes, benzocarbocycles, and N‐heterocycle derivatives in good to excellent yields. This method features easily accessible starting materials, simple operation, broad substrate scope, good functional‐group tolerance and short reaction times (see scheme).