Tungsten catalysed decarboxylative [3+2] cycloaddition aromatization: one-pot synthesis of trifluoromethyl-pyrrolo[2,1-a]isoquinolines with visible light irradiation

Yu, Daohong1,2,3; Liu, Yungen1,4; Che, Chi-Ming1,2,5,6

2022-04-01

10.1039/d2qo00401a

Organic Chemistry Frontiers   影响因子和分区

2052-4129

The pyrrolo[2,1-a]isoquinoline core structure is prevalent in marine natural products and its fluorinated derivatives are potential medicinal compounds. Herein is described a tungsten-catalysed decarboxylative [3 + 2] cycloaddition aromatization process that could be used to construct trifluoromethyl-pyrrolo[2,1-a]isoquinolines. This photocatalytic reaction tolerates a panel of functional groups including ester, nitrile, ketone and alkene (24 examples, up to 94% yield). The pharmaceutically useful trifluoromethyl substituted lamellarin derivatives and late-stage derivatization of drugs are facilely accessible via the current synthetic approach.

SCI ; EI

英语

第一 ; 通讯

Guangdong Major Project of Basic and Applied Research[2019B030302009] ; Guangdong Provincial Key Laboratory of Catalysis[2020B121201002] ; Science, Technology and Innovation Commission of Shenzhen Municipality[JCYJ20180508162429786]

Chemistry

Chemistry, Organic

WOS:000784902200001

ROYAL SOC CHEMISTRY

20221912090713

Catalysis ; Ketones

Tungsten and Alloys:543.5 ; Chemical Reactions:802.2 ; Organic Compounds:804.1

Web of Science

1.Southern Univ Sci & Technol, Dept Chem, Shenzhen 518055, Guangdong, Peoples R China
2.Univ Hong Kong, Dept Chem, State Key Lab Synthet Chem, Pokfulam Rd, Hong Kong, Peoples R China
3.Gannan Normal Univ, Key Lab Organo Pharmaceut Chem Jiangxi Prov, Ganzhou 341000, Peoples R China
4.Southern Univ Sci & Technol, Guangdong Prov Key Lab Catalysis, Shenzhen 518055, Guangdong, Peoples R China
5.HKU Shenzhen Inst Res & Innovat, Shenzhen 518055, Guangdong, Peoples R China
6.Lab Synthet Chem & Chem Biol Ltd, New Terr, Units 1503-1511,15-F,Bldg 17W,Hong Kong Sci & Tec, Hong Kong, Peoples R China

Yu, Daohong,Liu, Yungen,Che, Chi-Ming. Tungsten catalysed decarboxylative [3+2] cycloaddition aromatization: one-pot synthesis of trifluoromethyl-pyrrolo[2,1-a]isoquinolines with visible light irradiation[J]. Organic Chemistry Frontiers,2022.

Yu, Daohong,Liu, Yungen,&Che, Chi-Ming.(2022).Tungsten catalysed decarboxylative [3+2] cycloaddition aromatization: one-pot synthesis of trifluoromethyl-pyrrolo[2,1-a]isoquinolines with visible light irradiation.Organic Chemistry Frontiers.

Yu, Daohong,et al."Tungsten catalysed decarboxylative [3+2] cycloaddition aromatization: one-pot synthesis of trifluoromethyl-pyrrolo[2,1-a]isoquinolines with visible light irradiation".Organic Chemistry Frontiers (2022).