scispace - formally typeset
Open AccessJournal ArticleDOI

Palladium‐Catalyzed Fluorosulfonylvinylation of Organic Iodides

Reads0
Chats0
TLDR
A palladium-catalyzed fluorosulfonylvinylation reaction of organic iodides is described, demonstrated in the successful syntheses of eighty-eight otherwise difficult to access compounds, in up to 99 % yields, including the unprecedented 2-heteroarylethenesulfonyl fluorides and 1,3-dienylsulfonyL fluorides.
Abstract
A palladium-catalyzed fluorosulfonylvinylation reaction of organic iodides is described. Catalytic Pd(OAc)2 with a stoichiometric amount of silver(I) trifluoroacetate enables the coupling process between either an (hetero)aryl or alkenyl iodide with ethenesulfonyl fluoride (ESF). The method is demonstrated in the successful syntheses of eighty-eight otherwise difficult to access compounds, in up to 99 % yields, including the unprecedented 2-heteroarylethenesulfonyl fluorides and 1,3-dienylsulfonyl fluorides.

read more

Content maybe subject to copyright    Report

Citations
More filters
Journal ArticleDOI

The growing applications of SuFEx click chemistry

TL;DR: This review discusses the growing number of applications of SuFEx, which can be found in nearly all areas of modern chemistry; from drug discovery to materials science.
Journal ArticleDOI

SuFEx-enabled, agnostic discovery of covalent inhibitors of human neutrophil elastase

TL;DR: Evaluation of the ever-growing collection of SuFExable compounds toward various biological assays unexpectedly revealed a selective and covalent hNE inhibitor: benzene-1,2-disulfonyl fluoride.
Journal ArticleDOI

Sulfonyl Fluorides (SFs) : More Than Click Reagents?

TL;DR: Sulfonyl fluoride (SF) containing substances are currently attracting enormous attention among practitioners of both chemical biology and synthetic organic chemistry as mentioned in this paper, and the groups of Jones and Liskam...
Journal ArticleDOI

Recent advances towards sulfur (VI) fluoride exchange (SuFEx) click chemistry

TL;DR: The Sulfur (VI) Fluoride Exchange Reaction (SuFEx) was developed by Sharpless and co-workers in 2014 and is a promising new click reaction that rests on the extraordinary elevated reactivity of sulfonyl fluorides and fluorosulfates with desired appropriate nucleophiles including silyl ethers and amines as discussed by the authors.
Journal ArticleDOI

SuFEx Chemistry of Thionyl Tetrafluoride (SOF4) with Organolithium Nucleophiles: Synthesis of Sulfonimidoyl Fluorides, Sulfoximines, Sulfonimidamides, and Sulfonimidates

TL;DR: This method provides rapid and modular access to sulfonimidoyl fluorides (R1 -N=SOFR2), another array of versatile SuFEx connectors with readily tunable reactivity of the S-F handle, and the controlled projection of sulfur-carbon links at the sulfur center of SOF4 -derived iminosulfur oxydifluorides.
References
More filters
Journal ArticleDOI

The resurgence of covalent drugs

TL;DR: The prevalence and pharmacological advantages of covalent drugs are surveyed, how potential risks and challenges may be addressed through innovative design, and the broad opportunities provided by targeted covalENT inhibitors are presented.
Journal ArticleDOI

Sulfur(VI) Fluoride Exchange (SuFEx): Another Good Reaction for Click Chemistry

TL;DR: It is shown that proton or silicon centers can activate the exchange of S�F bonds for SO bonds to make functional products, and that the sulfate connector is surprisingly stable toward hydrolysis.
Journal ArticleDOI

ON01910, a non-ATP-competitive small molecule inhibitor of Plk1, is a potent anticancer agent

TL;DR: ON01910, a small molecule inhibitor of Plk1 activity, which induces mitotic arrest of tumor cells characterized by spindle abnormalities leading to their apoptosis, showed strong synergy with several chemotherapeutic agents, often inducing complete regression of tumors.
Related Papers (5)