Pd/IHept-Catalyzed Regioselective Annulation of 2-Fluoroallyl Carbonates with Enaminones: Synthesis of Fully Substituted Pyrroles

Huijun Qian; Wenhao Liu; Junqi Su; Zhengjun Shi; Meng-Yang Hu; Leiyang Lv; Zhiping Li

doi:10.1055/a-2436-0471

Synthesis, Inhaltsverzeichnis

Synthesis 2025; 57(06): 1180-1188
DOI: 10.1055/a-2436-0471

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Pd/IHept-Catalyzed Regioselective Annulation of 2-Fluoroallyl Carbonates with Enaminones: Synthesis of Fully Substituted Pyrroles

Huijun Qian

^aKey Laboratory of Advanced Light Conversion Materials and Biophotonics, School of Chemistry and Life Resources, Renmin University of China, Beijing 100872, P. R. of China

,

Wenhao Liu

^aKey Laboratory of Advanced Light Conversion Materials and Biophotonics, School of Chemistry and Life Resources, Renmin University of China, Beijing 100872, P. R. of China

,

Junqi Su

^aKey Laboratory of Advanced Light Conversion Materials and Biophotonics, School of Chemistry and Life Resources, Renmin University of China, Beijing 100872, P. R. of China

,

Zhengjun Shi

^bFujian Zhongxin Fluoromaterial Gaobao Science and Technology Co., Ltd., No. 8, Tongkeng Village, Wenjiao, Qingliu County, Sanming, Fujian Province, P. R. of China

,

Meng-Yang Hu

^cDreamChem (Tianjin) Co., Ltd., No. 4, Haitai Development 2nd Road, Binhai High-tech Zone, Tianjin, P. R. of China

,

Leiyang Lv∗

^aKey Laboratory of Advanced Light Conversion Materials and Biophotonics, School of Chemistry and Life Resources, Renmin University of China, Beijing 100872, P. R. of China

,

Zhiping Li∗

^aKey Laboratory of Advanced Light Conversion Materials and Biophotonics, School of Chemistry and Life Resources, Renmin University of China, Beijing 100872, P. R. of China

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Abstract

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Abstract

The Pd/IHept-catalyzed regioselective annulation of 2-fluoroallyl carbonates with enaminones has been developed. This method allows the efficient synthesis of a variety of fully substituted pyrroles with high regioselectivity. Experimental data demonstrate that the fluorinated alkene intermediate is initially formed, which then undergoes C–F cleavage/annulation to give the pyrrole products. Furthermore, it is evident that both the substitution and annulation steps necessitate the participation of the Pd/IHept catalyst.

Keywords

Pd/NHC catalysis - C–F bond cleavage - enaminones - annulation - fluoroallylation

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