Synthesis
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
a   Key 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
a   Key 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
a   Key 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
b   Fujian 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
c   DreamChem (Tianjin) Co., Ltd., No. 4, Haitai Development 2nd Road, Binhai High-tech Zone, Tianjin, P. R. of China
,
Leiyang Lv
a   Key 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
a   Key Laboratory of Advanced Light Conversion Materials and Biophotonics, School of Chemistry and Life Resources, Renmin University of China, Beijing 100872, P. R. of China
› Author Affiliations
This work was supported by the Outstanding Innovative Talents Cultivation Funded Programs 2023 of Renmin University of China, the National­ Natural Science Foundation of China (22201300, 22071266), the Fundamental Research Funds for the Central Universities, and the Research Funds of Renmin University of China (24XNKJ27).


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.

Supporting Information



Publication History

Received: 31 July 2024

Accepted after revision: 07 October 2024

Accepted Manuscript online:
07 October 2024

Article published online:
28 October 2024

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