Copper-Catalyzed Trifluoromethylation and Bicyclizations of 1,7-Enynes Leading to Fused Polycycles

• Published in: Advanced synthesis & catalysis Vol. 358; no. 21; pp. 3435 - 3442
• Main Authors: Wang, Qiang, Song, Hongjian, Liu, Yuxiu, Song, Haibin, Wang, Qingmin
• Format: Journal Article
• Language: English
• Published: WEINHEIM Blackwell Publishing Ltd 03.11.2016; Wiley
• Subjects: Agricultural chemicals; Catalysis; Chemistry; Chemistry, Applied; Chemistry, Organic; Fungi; fungicidal activity; Fungicides; fused polycycles; Indene; Organic chemistry; Physical Sciences; radical cascade reaction; Radicals; Science & Technology; Synthesis (chemistry); trifluoromethylation; fungicidal activity; CARBOCYCLIZATION; radical cascade reaction; BOND FORMATION; fused polycycles; ALKENES; ARYLTRIFLUOROMETHYLATION; DEAROMATIZATION ACCESS; LIGHT-INDUCED TRIFLUOROMETHYLATION; CONSTRUCTION; FLUORINE; trifluoromethylation; CYCLIZATION; 1,N-ENYNES
• ISSN: 1615-4150; 1615-4169
• DOI: 10.1002/adsc.201600500

A series of trifluoromethyl‐containing heterocycles, like indene and dihydroquinolinone or dihydrocoumarin‐fused tetracyclic compounds have been prepared using copper‐catalyzed cascade reaction of benzene‐tethered 1,7‐enynes. A study of the mechanism indicated that radical trifluoromethylation and sequential 6‐exo‐dig/5‐endo‐trig bicyclization processes were involved in this protocol. Moreover, some selected products showed certain fungicidal activities against 14 kinds of plant fungi which means that these functionalized tetracyclic compounds might be used in the agrochemical field.