Hydrofluoroether Synthesis through One‐Pot Anodic Iodoalkoxylation of Alkenes DOI Creative Commons
Martín Becerra‐Ruiz,

Bethan Winterson,

Edwin G. Pérez

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 15, 2024

Abstract The incorporation of carbon‐fluorine bonds can profoundly influence the chemical and physical properties drugs, agrochemicals, materials. Different methods allow installation CF 3 , 2 H units C−F including trifluoro‐ difluoromethoxylations, reflecting limited diversity reactions available to synthetic chemists. We introduce 2,2,2‐trifluoroethoxy group through an electro‐oxidative iodination alkenes as a versatile substituent for fluorine An iodoarene serves unusual iodine source facilitating 1,2‐iodoalkoxylation broad range industrially relevant aliphatic in high yields (31–98%) showing Markovnikov regioselectivity.

Language: Английский

Electrochemical Difluoromethylation of Electron-Rich Olefins DOI

Shinan Luan,

Thomas Castanheiro, Thomas Poisson

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(10), P. 1678 - 1682

Published: March 3, 2023

The electrochemical difluoromethylation of electron-rich olefins (enamides and styrene derivatives) is disclosed. addition the electrogenerated difluoromethyl radical from corresponding sodium sulfinate (i.e., HCF2SO2Na) to enamides styrenes in an undivided cell allowed formation a large panel difluoromethylated building blocks good excellent yields (42 examples, 23-87% yields). A plausible unified mechanism was suggested according control experiments cyclic voltammetry measurements.

Language: Английский

Citations

16
Electrochemical bromination of enamides with sodium bromide DOI

Shinan Luan,

Thomas Castanheiro, Thomas Poisson

et al.

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(6), P. 3429 - 3434

Published: Jan. 1, 2024

The electrochemical bromination of enamide derivatives was developed using inexpensive and non-toxic sodium bromide (NaBr).

Language: Английский

Citations

5
Electrochemical Hydrosilylation of Electron‐Withdrawing Alkenes DOI Open Access

He‐Yang Zhou,

Lu‐Qi Fei,

Jialan Zhang

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(10), P. 1591 - 1595

Published: May 3, 2023

Abstract In the presence of Suginome reagent (PhMe 2 Si−Bpin), a large panel electron‐withdrawing alkenes was successfully converted into hydrosilylated product in good to excellent yields. This direct electrochemical hydrosilylation does not require exogenous oxidants and catalysts. Preliminary mechanistic study supported involvement silyl radical, which reacted on alkene. magnified image

Language: Английский

Citations

11
Electrochemical cascade reactions: an account of recent developments for this modern strategic tool in the arsenal of chemical synthesis DOI
Manoj Kumar Yadav, Sushobhan Chowdhury

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(24), P. 10144 - 10181

Published: Jan. 1, 2023

The electrochemical cascade process majorly satisfies the essential criteria of green synthesis. Being an Integrated synthetic strategy it can produce more molecules in a shorter time and thus provides modern strategic tool arsenal chemists.

Language: Английский

Citations

11
Electrochemical Borylation of Electron‐Deficient Alkenes and Allenoates DOI Creative Commons

Maude Aelterman,

Philippe Jubault, Thomas Poisson

et al.

European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 26(17)

Published: March 3, 2023

Abstract The electrochemical borylation of electro‐deficient alkenes and allenoates is disclosed. In an undivided cell under galvanostatic conditions a panel Michael acceptor was readily reacted. reaction offered access to versatile borylated building blocks in good excellent yields (20 examples, 47 % 91 yields). A plausible mechanism, based on the literature precedent suggested.

Language: Английский

Citations

8
Synthesis of Cyclopropylamines through an Electro-Induced Hofmann Rearrangement DOI
André B. Charette, Thomas Poisson, Philippe Jubault

et al.

Synthesis, Journal Year: 2023, Volume and Issue: 55(18), P. 2943 - 2950

Published: March 9, 2023

Abstract A practical access to cyclopropylamines from the corresponding amides is disclosed, according an electro-induced Hofmann rearrangement. In undivided cell under galvanostatic conditions, a panel of cyclopropyl was readily converted into amines (17 examples, 23% 94% yield). This reaction allowed easy versatile and complementary existing methods.

Language: Английский

Citations

8
Electrode-switchable: exploring this new strategy to achieve regiodivergent azidoiodination of alkenes DOI

Xin-Lei Sun,

Chen-Xi Xia,

Yue Ren

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(8), P. 2189 - 2194

Published: Jan. 1, 2024

An “electrode-switchable” organic electrochemistry method for the azidoiodination of alkenes, where choice anode dictates regiodivergent alkene azidoiodination, reveals a novel pathway controlled regioisomers.

Language: Английский

Citations

2
Transformation of Unactivated Alkenes into Iodohydrins and β‐Iodoethers using Iodine‐DMSO as a Reagent Combination DOI
Reetu Reetu, Raghuram Gujjarappa,

Yaqoob A. Teli

et al.

ChemistrySelect, Journal Year: 2024, Volume and Issue: 9(1)

Published: Jan. 2, 2024

Abstract A combination of reagents using I 2 and DMSO has been established for the selective transformation unactivated alkenes into iodohydrins β ‐iodoethers. The developed approach was served by dual roles as an oxidant well a hydroxylating agent under different solvent systems at 85 °C. method holds operational simplicity is consistent with wide range substituted to deliver ‐iodoethers in yields up 86 %. formation are MeCN course reaction examined GC‐MS studies DFT method.

Language: Английский

Citations

1
The Electrochemical trans-Chloroformyloxylation of Unactivated Alkenes DOI

Jona Queder,

Gerhard Hilt

Synlett, Journal Year: 2024, Volume and Issue: 35(16), P. 1906 - 1908

Published: March 20, 2024

Abstract An attempted aryl selenium-catalyzed formation of cis-chlorohydrins from alkenes was unsuccessful but led to an electrochemical investigation for the trans-selective chloroformyloxylation cyclic and acyclic in moderate good yields. Interestingly, when 1,1-disubstituted were used, corresponding vinyl chloride derivatives obtained, application 1-phenylcyclohex-1-ene allyl derivative.

Language: Английский

Citations

1
Hydrofluoroether Synthesis through One‐Pot Anodic Iodoalkoxylation of Alkenes DOI Creative Commons
Martín Becerra‐Ruiz,

Bethan Winterson,

Edwin G. Pérez

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 15, 2024

Abstract The incorporation of carbon‐fluorine bonds can profoundly influence the chemical and physical properties drugs, agrochemicals, materials. Different methods allow installation CF 3 , 2 H units C−F including trifluoro‐ difluoromethoxylations, reflecting limited diversity reactions available to synthetic chemists. We introduce 2,2,2‐trifluoroethoxy group through an electro‐oxidative iodination alkenes as a versatile substituent for fluorine An iodoarene serves unusual iodine source facilitating 1,2‐iodoalkoxylation broad range industrially relevant aliphatic in high yields (31–98%) showing Markovnikov regioselectivity.

Language: Английский

Citations

1