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CC BY 4.0 · Pharmaceutical Fronts 2020; 02(02): e94-e99
DOI: 10.1055/s-0040-1712998
Original Article
Georg Thieme Verlag KG Stuttgart · New York

Rhodium-Catalyzed Ortho-Vinylation of 2-Arylpyridines and Its Application in the Total Synthesis of Palmatine

Shan Lv
1   Sichuan Engineering Laboratory for Plant-Sourced Drug and Research Center for Drug Industrial Technology, Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry, West China School of Pharmacy, Sichuan University, Chengdu, China
,
Ruifang Nie
1   Sichuan Engineering Laboratory for Plant-Sourced Drug and Research Center for Drug Industrial Technology, Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry, West China School of Pharmacy, Sichuan University, Chengdu, China
,
Lingmei Guo
1   Sichuan Engineering Laboratory for Plant-Sourced Drug and Research Center for Drug Industrial Technology, Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry, West China School of Pharmacy, Sichuan University, Chengdu, China
,
Yang Zheng
1   Sichuan Engineering Laboratory for Plant-Sourced Drug and Research Center for Drug Industrial Technology, Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry, West China School of Pharmacy, Sichuan University, Chengdu, China
,
Yanzhao Liu
1   Sichuan Engineering Laboratory for Plant-Sourced Drug and Research Center for Drug Industrial Technology, Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry, West China School of Pharmacy, Sichuan University, Chengdu, China
,
Li Guo
1   Sichuan Engineering Laboratory for Plant-Sourced Drug and Research Center for Drug Industrial Technology, Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry, West China School of Pharmacy, Sichuan University, Chengdu, China
,
Yong Wu
1   Sichuan Engineering Laboratory for Plant-Sourced Drug and Research Center for Drug Industrial Technology, Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry, West China School of Pharmacy, Sichuan University, Chengdu, China
› Author Affiliations Acknowledgments We are grateful for support from the National Natural Science Foundation of China (NSFC; grants 81373259 and 81573286).
Further Information

Publication History

Publication Date:
30 June 2020 (online)

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Abstract

An efficient protocol by Rh-catalyzed direct C–H vinylation of 2-arylpyridines with a commercially available and air-stable potassium vinyl donor has been developed. This method affords the corresponding pyridinyl styrene derivative with moderate to excellent yields under mild conditions, which is extremely beneficial to the total synthesis of the natural product palmatine.

Keywords

rhodium-catalyzed - C–H activation - ortho-vinylation - potassium vinyltrifluoroborate - palmatine
 

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