625091-78-3

Upstream product

• 103273-01-4 2-bromo-4-tert-butylaniline 
• 769-92-6 4-tert-Butylaniline 
• 1003-98-1 2-bromo-4-fluoroaniline 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 1448756-45-3 5-fluoro-2,3-diphenyl-1-tosylindole 
• 10219-00-8 N-(4-fluorophenyl)-N,4-dimethylbenzenesulfonamide 

Relevant academic research and scientific papers

Directing-group-assisted markovnikov-selective hydrothiolation of styrenes with thiols by photoredox/cobalt catalysis

In contrast with the well-developed radical thiol-ene reaction to access anti-Markovnikov-type products, the research on the catalytic Markovnikov-selective hydrothiolation of alkenes is very restricted. Because of the catalyst poisoning of metal catalysts by organosulfur compounds, limited examples of transition-metal-catalyzed thiol-ene reactions have been reported. However, in this work, a directing-group-assisted hydrothiolation of styrenes with thiols by photoredox/cobalt catalysis is found to proceed smoothly to afford Markovnikov-type sulfides with excellent regioselectivity.

Stereoinversion of Unactivated Alcohols by Tethered Sulfonamides

The direct, catalytic substitution of unactivated alcohols remains an undeveloped area of organic synthesis. Moreover, catalytic activation of this difficult electrophile with predictable stereo-outcomes presents an even more formidable challenge. Described herein is a simple iron-based catalyst system which provides the mild, direct conversion of secondary and tertiary alcohols to sulfonamides. Starting from enantioenriched alcohols, the intramolecular variant proceeds with stereoinversion to produce enantioenriched 2- and 2,2-subsituted pyrrolidines and indolines, without prior derivatization of the alcohol or solvolytic conditions.

Visible-Light-Driven Neutral Nitrogen Radical Mediated Intermolecular Styrene Difunctionalization

A neutral nitrogen radical-mediation strategy, wherein the existing N-H moiety of substrates serves as a neutral nitrogen radical precursor to enable room-temperature intermolecular radical difunctionalization of styrenes under photoredox catalysis, is reported. The reaction shows high functional group tolerance and substrate scope with respect to both components, giving the corresponding products with generally good yields. Preliminary control experiments and DFT calculations are performed to explain the reaction mechanism.

One-Pot Synthesis of Indole-3-acetic Acid Derivatives through the Cascade Tsuji-Trost Reaction and Heck Coupling

A practical palladium-mediated cascade Tsuji-Trost reaction/Heck coupling of N-Ts o-bromoanilines with 4-acetoxy-2-butenonic acid derivatives using a Pd(OAc)2/P(o-tol)3/DIPEA system is described for a straightforward synthesis of indole-3-acetic acid derivatives. This methodology was successfully applied to synthesize various substituted indole/azaindole-3-acetic acid derivatives and Almotriptan, which is a drug for the acute treatment of migraines. Moreover, a plausible cyclization mechanism has been proposed.

Platform for Ring-Fluorinated Benzoheterole Derivatives: Palladium-Catalyzed Regioselective 1,1-Difluoroallylation and Heck Cyclization

The synthesis of difluoromethylene-containing heterocycles was achieved via the palladium-catalyzed 1,1-difluoroallylation of heteronucleophiles followed by intramolecular Heck reaction. The allylic substitution of 3-bromo-3,3-difluoropropene was regiosel

Tris(trimethylsilyl)silane and visible-light irradiation: A new metal- and additive-free photochemical process for the synthesis of indoles and oxindoles

A combined tris(trimethylsilyl)silane and visible-light-promoted intramolecular reductive cyclization protocol for the synthesis of indoles and oxindoles has been developed. This straightforward and efficient method shows tolerance towards a broad spectru

Oxidative fluorination of N-arylsulfonamides

We report a late stage oxidative nucleophilic fluorination of N-arylsulfonamides, a class of compounds so far not considered as precursors to 4-fluorophenyl sulfonamides. By installing a para-positioned tert-butyl substituent on the aniline, oxidative fluorination takes place regioselectively in the presence of HF·pyridine and PIDA. This methodology has been shown to give good yields for a variety of ortho- and meta-functionalised N-arylsulfonamides and has been adapted for radiofluorination to give 4-[18F]fluorophenyl sulfonamides under carrier added conditions.

Synthetic use of 1,1,2,2-tetraphenyldisilane for the preparation of biaryls through the intramolecular free radical ipso-substitution of N-(2-bromoaryl)arenesulfonamides

Treatment of various N-methyl-N-(2-bromoaryl)arenesulfonamides (1a-g, 1i, and 1m) with 1,1,2,2-tetraphenyldisilane and AIBN under heating conditions gave the corresponding biaryl products (2a-g, 2i, and 2m) in moderate yields through the intramolecular radical ipso-substitution. However, N-H free N-(2-bromoaryl)arenesulfonamides 1h and 2-bromoaryl arenesulfonate 1j did not give the corresponding biarys. 1,1,2,2-Tetraphenyldisilane is the most effective reagent for 1,5-ipso-substitution on the sulfonamides among typical radical reagents such as diphenylsilane, tributyltin hydride, tris(trimethylsilyl)silane, and 1,1,2,2-tetraphenyldisilane. Furthermore, 1,1,2,2-tetraphenyldisilane has the advantages of low toxicity, stability, and ease of preparation.