Recent advances in photochemical and electrochemical strategies for the synthesis of sulfonyl fluorides

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 11(1), P. 217 - 235

Published: Nov. 14, 2023

This review summarizes the latest achievements in photochemical and electrochemical strategies for synthesis of sulfonyl fluorides focuses on novel features proposed mechanisms.

Language: Английский

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Organomediated electrochemical fluorosulfonylation of aryl triflates via selective C–O bond cleavage

Nature Communications, Journal Year: 2023, Volume and Issue: 14(1)

Published: Oct. 31, 2023

Although aryl triflates are essential building blocks in organic synthesis, the applications as radical precursors limited. Herein, we report an organomediated electrochemical strategy for generation of radicals from triflates, providing a useful method synthesis sulfonyl fluorides feedstock phenol derivatives under very mild conditions. Mechanistic studies indicate that key to success is use catalytic amounts 9, 10-dicyanoanthracene mediator, enabling selectively active form via orbital-symmetry-matching electron transfer, realizing anticipated C-O bond cleavage by overcoming competitive S-O cleavage. The transition-metal-catalyst-free protocol shows good functional group tolerance, and may overcome shortages known methods fluoride synthesis. Furthermore, this has been used modification formal bioactive molecules or tetraphenylethylene (TPE) derivative with improved quantum yield fluorescence.

Language: Английский

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Electroreductive hydroxy fluorosulfonylation of alkenes

Nature Communications, Journal Year: 2023, Volume and Issue: 14(1)

Published: Dec. 13, 2023

An electroreductive strategy for radical hydroxyl fluorosulfonylation of alkenes with sulfuryl chlorofluoride and molecular oxygen from air is described. This mild protocol displays excellent functional group compatibility, broad scope, good scalability, providing convenient access to diverse β-hydroxy sulfonyl fluorides. These fluoride products can be further converted valuable aliphatic fluorides, β-keto β-alkenyl Further, some these showed inhibitory activity against Botrytis cinerea or Bursaphelenchus xylophilus, which could useful potent agrochemical discovery. Preliminary mechanistic studies indicate that this transformation achieved through rapid O2 interception by the alkyl subsequent reduction peroxy radical, outcompete other side reactions such as chlorine atom transfer, hydrogen Russell fragmentation.

Language: Английский

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Radical Hydro-Fluorosulfonylation of Propargylic Alcohols via Electron Donor–Acceptor Photoactivation

Organic Letters, Journal Year: 2024, Volume and Issue: 26(7), P. 1410 - 1415

Published: Feb. 15, 2024

A radical hydro-fluorosulfonylation of propargyl alcohols with FSO2Cl is presented based on the photoactivation electron donor–acceptor (EDA) complex. The reaction avoids requirement for photocatalysts, bases, hydrogen donor reagents, any other additives, and harsh conditions, enabling facile synthesis various functionalized γ-hydroxy (E)-alkenylsulfonyl fluorides. These multifunctional sulfonyl fluorides can be further diversified, providing access to privileged molecules biological relevance.

Language: Английский

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Electrochemical conversion of organic compounds and inorganic small molecules

Science China Chemistry, Journal Year: 2024, Volume and Issue: 67(10), P. 3223 - 3246

Published: July 9, 2024

Language: Английский

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Hydrosulfonylation of Unactivated Alkenes and Alkynes by Halogen-Atom Transfer (XAT) Cleavage of S^VI–F Bond

Organic Letters, Journal Year: 2023, Volume and Issue: 25(48), P. 8722 - 8726

Published: Nov. 29, 2023

A photochemical halogen-atom transfer (XAT) method for generating sulfonyl radicals from aryl fluorides has been developed. It allows the hydrosulfonylation of unactivated alkenes, which was challenging to achieve through our previous single-electron route. This reaction excellent functional group tolerance and substrate scope under mild conditions.

Language: Английский

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Base metal chemistry and catalysis

Cell Reports Physical Science, Journal Year: 2023, Volume and Issue: 4(9), P. 101548 - 101548

Published: Aug. 21, 2023

This perspective provides an entry-level conversation concerning base metal catalysis as a green and sustainable solution in industrial academic contexts. We establish definition of "base metal," challenging readers to consider the ethical implications sourcing. explore what it means be "sustainable" provide information on current efforts synthetic chemistry. examples catalytic trends transformations popular fields such cross-coupling small-molecule conversion, highlighting relevant systems. Finally, we social context—for example, decisions related catalyst development are often driven by factors including costliness, safety, adoptability (whether society will accept its usage), performance. How do move forefront? Is concerned if materials fabricated from cheaper more abundant sources? does chemistry community guide this knowledge translation?

Language: Английский

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C(sp³)–H fluorosulfonylvinylation/aza-Michael addition approach to FSO₂-functionalized tetrahydropyridines

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(15), P. 3805 - 3810

Published: Jan. 1, 2023

We have developed an efficient approach for the synthesis of FSO 2 -functionalized tetrahydropyridines from propargyl alcohols, Cl, and anilines.

Language: Английский

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Electrifying synthesis of organosilicon compounds – from electrosynthesis to electrocatalysis

Inorganic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(5), P. 1382 - 1394

Published: Jan. 1, 2023

Organosilicon compounds via electrosynthesis – the recent developments and further challenges.

Language: Английский

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Ni-Catalyzed Hydrosulfonylation of Alkenes with Aromatic Iodides and K₂S₂O₅

Organic Letters, Journal Year: 2023, Volume and Issue: 25(44), P. 8043 - 8047

Published: Oct. 30, 2023

Hydrosulfonylation of alkenes with readily available aromatic iodides via a SO2-insetion strategy is presented. The combination non-noble Ni catalysis (iPr)3SiH as the final reductant enables efficient formation aryl and heteroaryl sulfinate intermediates, which undergo Michael-type additions to electron-deficient for initiating hydrosulfonylation process. Moreover, superiority this protocol demonstrated by broad substrate scope good functional group compatibility.

Language: Английский

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