Photo/Ni dual-catalyzed radical defluorinative sulfonylation to synthesizegem-difluoro allylsulfones DOI Open Access

Yiran Xu,

Shengchun Wang, Zhao Liu

et al.

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(25), P. 3707 - 3710

Published: Jan. 1, 2023

Radical defluorinative functionalization of α-trifluoromethyl styrenes represents an effective way toward gem-difluoroalkenes. There are general interests in developing novel synthetic protocols for with various types radicals. However, reports on the preparation gem-difluoro allylsulfones via S-centered radical pathway limited. Herein, we developed a photo/nickel dual-catalyzed sulfonylation that rapidly and reliably synthesizes allylsulfones. The merit this protocol is exhibited by its mild conditions wide scope, thus providing strategy sulfonyl participating coupling.

Language: Английский

Visible-Light-Driven Sulfonation of α-Trifluoromethylstyrenes: Access to Densely Functionalized CF3-Substituted Tertiary Alcohol DOI
Yixuan Chen, Zhujun Wang, Jun‐An Xiao

et al.

Organic Letters, Journal Year: 2021, Volume and Issue: 23(16), P. 6558 - 6562

Published: Aug. 3, 2021

Reported herein is a visible-light-induced sulfonation of α-trifluoromethylstyrenes with sodium sulfinates, which provides series α-trifluoromethyl-β-sulfonyl tertiary alcohols. This new synthetic protocol enabled by charge-transfer complex between oxygen and featuring broad substrate scope scalability. Excellent functional group compatibility chemoselectivity render this method suitable for pharmaceutically relevant molecules. In the presence D2O, deuteriotrifluorinated products were also obtained, further demonstrating flexibility potentials strategy.

Language: Английский

Citations

42

Electrochemical‐Induced Hydroxysulfonylation of α‐CF3 Alkenes to Access Tertiary β‐Hydroxysulfones DOI
Xu Luo, Shengchun Wang, Aiwen Lei

et al.

Advanced Synthesis & Catalysis, Journal Year: 2022, Volume and Issue: 364(5), P. 1016 - 1022

Published: Jan. 25, 2022

Abstract An electrochemical hydroxysulfonylation of α‐CF 3 alkenes was accomplished in this work. By using easily available sodium sulfinates as the sulfonylating agents, a series valuable α‐trifluoromethyl tertiary alcohols were synthesized under mild and environmentally friendly electrolysis conditions moderate to good yields. The preliminary mechanistic investigation indicates that difunctional reaction involves radical process via sulfonyl radical. Gram‐scale synthesis shows significant potential application protocol. magnified image

Language: Английский

Citations

30

Defluorinative C–C Bond-Forming Reaction of Trifluoromethyl Alkenes with gem-(Diborylalkyl)lithiums DOI
Haeun Kim,

Yujin Jung,

Seung Hwan Cho

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(14), P. 2705 - 2710

Published: April 5, 2022

We report the transition-metal-free defluorinative C-C bond-forming reaction of trifluoromethyl alkenes with gem-(diborylalkyl)lithiums. This synthetic strategy provides access to a variety 4,4-difluoro homoallylic diboronate esters, which serve as versatile intermediates in efficient preparation valuable gem-difluoroalkene derivatives. Further modifications are conducted demonstrate utility obtained esters.

Language: Английский

Citations

30

Defluorophosphorylation of fluoroalkyl peroxides for the synthesis of highly substituted furans DOI
Xue‐Qiang Chu,

Song‐Zhou Cai,

Jiawei Chen

et al.

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(5), P. 2000 - 2010

Published: Jan. 1, 2023

A highly tunable defluorophosphorylation of fluorinated peroxides for the preparation C 3,4-diphosphoryl furans and 4-monophosphoryl under conditions with no added transition metals is disclosed.

Language: Английский

Citations

17

Photo/Ni dual-catalyzed radical defluorinative sulfonylation to synthesizegem-difluoro allylsulfones DOI Open Access

Yiran Xu,

Shengchun Wang, Zhao Liu

et al.

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(25), P. 3707 - 3710

Published: Jan. 1, 2023

Radical defluorinative functionalization of α-trifluoromethyl styrenes represents an effective way toward gem-difluoroalkenes. There are general interests in developing novel synthetic protocols for with various types radicals. However, reports on the preparation gem-difluoro allylsulfones via S-centered radical pathway limited. Herein, we developed a photo/nickel dual-catalyzed sulfonylation that rapidly and reliably synthesizes allylsulfones. The merit this protocol is exhibited by its mild conditions wide scope, thus providing strategy sulfonyl participating coupling.

Language: Английский

Citations

17