Palladium-Catalyzed Fluoroalkylation via C(sp3)-S Bond Cleavage of Vinylsulfonium Salts

Yuan He; Zilong Huang; Juan Ma; Fei Huang; Jie Lin; Hongmei Wang; Bao Hua Xu; Yong Gui Zhou; Zhengkun Yu

doi:10.1021/acs.orglett.1c02172

Palladium-Catalyzed Fluoroalkylation via C(sp³)-S Bond Cleavage of Vinylsulfonium Salts

Yuan He, Zilong Huang, Juan Ma, Fei Huang, Jie Lin, Hongmei Wang^*, Bao Hua Xu, Yong Gui Zhou^*, Zhengkun Yu^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

24 Citations (Scopus)

Abstract

An interrupted Pummerer/palladium-catalyzed fluoro-alkylation strategy was developed for alkenyl C-H fluoroalkylthiolation. Palladium-catalyzed ring-opening fluoroalkylation via aliphatic C-S bond cleavage of the vinylsulfonium salts efficiently afforded fluoroalkylthiolated alkene derivatives from readily available alkene substrates and CsF. The protocol features broad substrate scopes and good functional group tolerance under an air atmosphere. The practicability of the synthetic method was demonstrated by transforming the multisubstituted alkene products to diverse fluoroalkylthiolated N-heterocycles.

Original language	English
Pages (from-to)	6110-6114
Number of pages	5
Journal	Organic Letters
Volume	23
Issue number	15
DOIs	https://doi.org/10.1021/acs.orglett.1c02172
Publication status	Published - 6 Aug 2021
Externally published	Yes

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title = "Palladium-Catalyzed Fluoroalkylation via C(sp3)-S Bond Cleavage of Vinylsulfonium Salts",

abstract = "An interrupted Pummerer/palladium-catalyzed fluoro-alkylation strategy was developed for alkenyl C-H fluoroalkylthiolation. Palladium-catalyzed ring-opening fluoroalkylation via aliphatic C-S bond cleavage of the vinylsulfonium salts efficiently afforded fluoroalkylthiolated alkene derivatives from readily available alkene substrates and CsF. The protocol features broad substrate scopes and good functional group tolerance under an air atmosphere. The practicability of the synthetic method was demonstrated by transforming the multisubstituted alkene products to diverse fluoroalkylthiolated N-heterocycles.",

author = "Yuan He and Zilong Huang and Juan Ma and Fei Huang and Jie Lin and Hongmei Wang and Xu, {Bao Hua} and Zhou, {Yong Gui} and Zhengkun Yu",

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year = "2021",

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doi = "10.1021/acs.orglett.1c02172",

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T1 - Palladium-Catalyzed Fluoroalkylation via C(sp3)-S Bond Cleavage of Vinylsulfonium Salts

AU - He, Yuan

AU - Huang, Zilong

AU - Ma, Juan

AU - Huang, Fei

AU - Lin, Jie

AU - Wang, Hongmei

AU - Xu, Bao Hua

AU - Zhou, Yong Gui

AU - Yu, Zhengkun

PY - 2021/8/6

Y1 - 2021/8/6

N2 - An interrupted Pummerer/palladium-catalyzed fluoro-alkylation strategy was developed for alkenyl C-H fluoroalkylthiolation. Palladium-catalyzed ring-opening fluoroalkylation via aliphatic C-S bond cleavage of the vinylsulfonium salts efficiently afforded fluoroalkylthiolated alkene derivatives from readily available alkene substrates and CsF. The protocol features broad substrate scopes and good functional group tolerance under an air atmosphere. The practicability of the synthetic method was demonstrated by transforming the multisubstituted alkene products to diverse fluoroalkylthiolated N-heterocycles.

AB - An interrupted Pummerer/palladium-catalyzed fluoro-alkylation strategy was developed for alkenyl C-H fluoroalkylthiolation. Palladium-catalyzed ring-opening fluoroalkylation via aliphatic C-S bond cleavage of the vinylsulfonium salts efficiently afforded fluoroalkylthiolated alkene derivatives from readily available alkene substrates and CsF. The protocol features broad substrate scopes and good functional group tolerance under an air atmosphere. The practicability of the synthetic method was demonstrated by transforming the multisubstituted alkene products to diverse fluoroalkylthiolated N-heterocycles.

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SN - 1523-7060

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EP - 6114

JO - Organic Letters

JF - Organic Letters

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ER -

Palladium-Catalyzed Fluoroalkylation via C(sp³)-S Bond Cleavage of Vinylsulfonium Salts

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