18006-66-1

Upstream product

• 128-37-0 2,6-di-tert-butyl-4-methyl-phenol 
• 1578268-91-3 N-methoxy-2-vinylbenzamide 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 98-59-9 p-toluenesulfonyl chloride 
• 17360-25-7 N-tosylvaline 
• 98-09-9 benzenesulfonyl chloride 
• 13633-26-6 4-phenylbut-1-en-3-yne 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 
• 540-80-7 tert.-butylnitrite 
• 766-97-2 4-n-methylphenylacetylene 

Relevant academic research and scientific papers

Iodide/tert-Butyl Hydroperoxide-Mediated Benzylic C–H Sulfonylation and Peroxidation of Phenol Derivatives

We disclose here the first iodine/tert-butyl hydroperoxide (I2/TBHP)-mediated benzylic C–H sulfonylation of phenol derivatives. This new methodology provides an economic, operationally simple and metal-free approach toward C(sp3)–S bond formation with medium to excellent yields at room temperature. Moreover, a novel sulfonylative and peroxidative bifunctionalization of phenol derivatives was also achieved by changing the amount of the oxidant. The reaction mechanism is exemplified via a radical pathway. (Figure presented.).

Transition-metal-free sulfonylations of methylthiolated alkynones to synthesize 3-sulfonylated thioflavones

A set of transition-metal-free NaI/TBHP-mediated sulfonylation cyclization reactions of methylthiolated alkynones with sulfonyl hydrazides was developed, by which various 3-sulfonylated thioflavones were prepared under mild reaction conditions. The features of this procedure included metal-free reaction conditions, ease of reagent handling, short reaction times, and a broad functional group tolerance.

Metal-free sulfonyl radical-initiated cascade cyclization to access sulfonated indolo[1,2-: A] quinolines

A metal-free cascade reaction was developed for the synthesis of indolo[1,2-a]quinoline derivatives from arylsulfonyl hydrazides and 1-(2-(arylethynyl)phenyl)indoles in the presence of TBAI/TBHP. Impressively, these products exhibit excellent fluorescence

A directing group free Pd(ii)-catalysed desulfitative C6-arylation of 2-pyridone using an arylsulfonyl chloride

A Pd(ii)-catalysed direct desulfitative arylation was realized at the C6-position of the 2-pyridone scaffold. Aryl sulfonyl chloride was used as an alternative arylating agent. The required site-selectivity occurred without the strategic installation of a heteroatom containing directing group. Preliminary mechanistic studies revealed that radical species were involved during this process.

Multiple-functionalizations of terminal alkynes with sodium sulfinates and tert-butyl nitrite: facile synthesis of 2H-azirines

A new, catalyst-free tandem annulation route to 2,2-disulfonyl-2H-azirines via multiple-functionalizations of terminal alkynes with sodium sulfinates and tert-butyl nitrite is described. The use of sodium sulfinates and tert-butyl nitrite enables the form

Silver-Catalyzed C(sp3)-H Sulfonylation for the Synthesis of Benzyl Sulfones Using Toluene Derivatives and α-Amino Acid Sulfonamides

We describe a simple and practical protocol for the synthesis of benzyl sulfones using readily available toluene derivatives and α-amino acid sulfonamides. The reaction proceeds to afford a broad range of benzyl sulfones in moderate to high yields under silver catalysis. The mechanism possibly involves a Minisci-type formation of α-aminoalkyl radical, homolytic cleavage of a N-S bond to generate a sulfonyl radical, and coupling of sulfonyl radical with a benzyl radical formed via hydrogen abstraction by sulfate anion radical. The practicality of the present reaction is demonstrated by a gram-scale synthesis and one-step synthesis of anticancer-active compound. The mechanism studies are conducted using radical scavengers and deuterated toluene.

Arylation ofgem-difluoroalkenes using a Pd/Cu Co-catalytic system that avoids β-fluoride elimination

PdII/CuIco-catalyze an arylation reaction ofgem-difluoroalkenes using arylsulfonyl chlorides to deliver α,α-difluorobenzyl products. The reaction proceeds through a β,β-difluoroalkyl-Pd intermediate that typically undergoes unimolecular β-F elimination to deliver monofluorinated alkene products in a net C-F functionalization reaction. However to avoid β-F elimination, we offer the β,β-difluoroalkyl-Pd intermediate an alternate low-energy route involving β-H elimination to ultimately deliver difluorinated products in a net arylation/isomerization sequence. Overall, this reaction enables exploration of new reactivities of unstable fluorinated alkyl-metal species, while also providing new opportunities for transforming readily available fluorinated alkenes into more elaborate substructures.

Dual Photoredox/Nickel-Catalyzed 1,4-Sulfonylarylation of 1,3-Enynes with Sulfinate Salts and Aryl Halides: Entry into Tetrasubstituted Allenes

A radical-mediated three-component 1,4-sulfonylarylation of 1,3-enynes with aryl iodides and sulfinate salts using cooperative photoredox/nickel catalysis is described. This protocol enables the synthesis of tetrasubstituted sulfonyl-containing allenes under redox-neutral conditions and provides a versatile 1,3-enyne 1,4-difunctionalization platform for the synthesis of a diverse range of tetrasubstituted allenes with high chemo- and regioselectivities, excellent functional group tolerance, and a broad substrate scope.

Copper-Catalyzed Aminosulfonylation of O-Homoallyl Benzimidates with Sodium Sulfinates to Access Sulfonylated 1,3-Oxazines

A facile copper-catalyzed aminosulfonylation of O-homoallyl benzimidates with sodium sulfinates in the presence of tert-butyl peroxybenzoate (TBPB) and XPhos ligand has been developed. By using this protocol, a variety of potentially bioactive 1,3-oxazines were directly synthesized. This method has the merits of a cheap catalyst, easily available and stable sulfone reagents, and simple operation.

A radical-mediated 1,3,4-trifunctionalization cascade of 1,3-enynes with sulfinates andtert-butyl nitrite: facile access to sulfonyl isoxazoles

An unprecedented indium-promoted three-component 1,3,4-trifunctionalization cascade of 1,3-enynes with sodium sulfinates andtert-butyl nitrite (TBN) to access 5-sulfonylisoxazolesvia[3+2] annulation is reported. By employing TBN as both the radical initiator and the N-O two atom unit, this method enables the formation of three new carbon-heteroatom bonds, C-S, C-N and C-O bonds, in a single reaction through a sequence of sulfonylation, isomerization, nitration and annulation with a broad substrate scope, excellent selectivity and the potential of late-stage functionalization of natural products.