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This article discusses the synthesis and characterization of thiosulfonates, sulfonyl hydrazides, and sulfonothioate compounds. The authors explore different methods for synthesizing these compounds and provide details on reaction conditions, yields, and physical properties. The text highlights the potential applications of these compounds in medicinal chemistry, drug design, and organic synthesis. The information provided can be valuable for researchers studying these compounds and their properties. The supporting information for the article is available online. [Extracted from the article]

First, the iodide anion is oxidized to molecular iodine at the anode, and then sulfonyl hydrazides B 13 b are utilized to generate sulfonyl radicals B I b for subsequent reactions. A possible reaction mechanism was proposed in which oxidation of the starting materials by bromine species (molecular bromine, hypobromite, bromate, perbromate and tribromide anions), generated by the anodic oxidation of the bromine anion, produced radical intermediates, the coupling of which led to the final products. Keywords: organosulfur compounds; electrosynthesis; halogen-mediated; eco-friendly; sulfonyl compounds; organic thiocyanates EN organosulfur compounds electrosynthesis halogen-mediated eco-friendly sulfonyl compounds organic thiocyanates 2799 2816 18 08/31/23 20230915 NES 230915 Graph 1 Introduction The significant influence of sulfur atoms on the electronic and physical properties of organic compounds has led to the widespread occurrence of sulfur functional groups in natural products, pharmaceuticals, and other biologically active compounds. The sulfonyl radical B I b is obtained by the oxidation of B 37a b with the iodine species obtained by oxidation of iodide at the anode. [Extracted from the article]

A copper-catalyzed radical cross-coupling of cyclobutanone oxime esters with sulfonyl hydrazides has been developed. The copper-based catalytic system proved crucial for cleavage of the C−C bond of cyclobutanone oximes and for selective C–S bond-formation involving persistent sulfonyl-metal radical intermediates. This protocol is distinguished by the low-cost catalytic system, which does not require ligand, base, or toxic cyanide salt, and by the use of readily accessible starting materials, as well as broad substrate scope, providing an efficient approach to various diversely substituted cyano-containing sulfones. [ABSTRACT FROM AUTHOR]

Because molecular iodine and hydrosilanes are stable to both air and moisture, reactions using these reagents are easy to operate and require mild reaction conditions. Molecular iodine and a hydrosilane were used to reduce N -sulfonyl aldimines to the corresponding N -alkylsulfonamides. This transformation is a practical method for the synthesis of N -alkylsulfonamides. [ABSTRACT FROM AUTHOR]

A tunable and practical transformation of structurally diverse sulfonyl hydrazides into thiosulfonates in the presence of Rongalite (NaHSO2 ·CH2 O) was developed. Transition-metal-free conditions, operational simplicity, and readily available reagents are the striking features of this protocol. It is the first example for the synthesis of thiosulfonates using sulfonyl hydrazides with the assistance of reductant. Additionally, the mechanistic studies revealed that this transformation probably undergoes via a reducing–coupling pathway. [ABSTRACT FROM AUTHOR]

A novel and efficient route for the synthesis of 3-sulfonylchroman-4-ones from α-sulfonyl o -hydroxyacetophenones with methyl sulfoxides via a MeONH2 ·HCl-mediated sequential methylenation/ conjugate- addition is described. Plausible reaction mechanisms are proposed and discussed. Various reaction conditions for this novel, one-pot, environmentally friendly conversion were investigated. [ABSTRACT FROM AUTHOR]

A convenient one-pot approach to the preparation of α-diazo-β-ketosulfones from sulfonyl chlorides is described. It involves the conversion of the sulfonyl chloride to sodium sulfinate, alkylation of the latter with α-haloketones followed by diazo transfer using the 'sulfonyl-azide-free' ('SAFE') protocol in aqueous medium. The simple and expedient method relies on readily available starting materials and provides facile access to a wide variety of valuable diazo reagents for organic synthesis. [ABSTRACT FROM AUTHOR]

A copper-catalyzed multicomponent reaction of sulfonyl azides, alkynes, and allylamines affording 2,3-dihydro-1 H -imidazo-[1,2-a]indoles in moderate yields is reported. Four C–N bonds are constructed- by way of azide-alkyne cycloaddition (CuAAC) and double Ullmann-type coupling reactions in a one-pot process. [ABSTRACT FROM AUTHOR]

A base-promoted direct synthesis of sulfinates from N -sulfonylhydrazones is described. Various N -sulfonylhydrazones, derived from aldehydes and ketones, are converted into the corresponding sulfinates in moderate to good yields. This protocol possesses many advantages such as readily available and stable starting materials, broad substrate scope, and metal-free reaction conditions. [ABSTRACT FROM AUTHOR]

An alternative metal-free, efficient and practical approach for the preparation of phosphinothioates is established via the aerobic oxidative cross-dehydrogenative coupling (CDC) of sulfonyl hydrazides with secondary phosphine oxides catalyzed by tetrabutylammonium iodide (TBAI) in the presence of atmospheric oxygen. The strategy provides an array of diverse phosphinothioates in good to excellent yields. Furthermore, two representative bioactive molecules are synthesized on up to gram scale by utilizing this method. [ABSTRACT FROM AUTHOR]

A convenient and efficient three-step synthesis of 2-(2,2-difluoroethoxy)-6-(trifluoromethyl)benzenesulfonyl chloride, the key building block of penoxsulam, is described. The main features of the synthesis include a regioselective lithiation and subsequent electrophilic substitution starting from commercially available 3-bromobenzotrifluoride to provide (2-bromo-6-(trifluoromethyl)phenyl)(propyl)sulfane, then a copper-catalyzed C–O coupling to introduce the difluoroethoxy moiety and chloroxidation conditions to give the desired sulfonyl chloride. [ABSTRACT FROM AUTHOR]

Sulfur-containing moieties, especially thioethers (sulfides), play pivotal roles in the functionalities of many natural products, pharmaceutical compounds, and organic materials. In this review, we summarize the recent synthetic protocols of thioethers using thiolating reagents, including sulfonyl chlorides, sodium sulfinates, and sulfonyl hydrazides, as the ideal starting materials. Representative mechanisms for different types of reaction are also discussed. 1 Introduction 2 Synthesis of Thioethers from Sulfonyl Chlorides 3 Synthesis of Thioethers from Sodium Sulfinates 4 Synthesis of Thioethers from Sulfonyl Hydrazides 5 Conclusion [ABSTRACT FROM AUTHOR]

A visible-light-mediated tandem sulfonylation/cyclization of vinyl azides with sulfonyl hydrazines was developed that provides an efficient and simple strategy for the synthesis of valuable 6-(sulfonylmethyl)phenanthridines with a broad substrate scope and satisfactory yields under mild conditions. [ABSTRACT FROM AUTHOR]

Sulfonylated pyridines were synthesized in moderate to excellent yields, with a wide scope of substituted pyridines and sulfinate salts as starting materials, by an iron-catalyzed SNAr reaction. This new methodology exhibits advantages for the synthesis of these useful substrates, such as the use of a readily available, inexpensive catalyst, prevention of the disproportionation of the sulfinate salts, and, more importantly, providing access to electron-rich pyridine substr [ABSTRACT FROM AUTHOR]

An efficient palladium-catalyzed cascade reaction of azides with isonitrile and amines is presented; it offers an alternative facile approach toward N-sulfonyl-, N-phosphoryl-, and N-acyl-functionalized guanidines in excellent yield. These series of substituted guanidines exhibit potential biological and pharmacological activities. In addition, the less reactive intermediate benzoyl carbodiimide could be isolated by silica gel column flash chromatography in moderate yield. [ABSTRACT FROM AUTHOR]

N-Sulfonyl ynamido-phosphonates were prepared from sulfonamides and bromo alkynylphosphonates through a direct coppercatalyzed coupling reaction. The substrates were obtained in good to excellent yields. The latter are valuable partners to react with nitrileoxides to form isoxazoles in good yields and with an exclusive regioselectivity. [ABSTRACT FROM AUTHOR]

A synthetic route to 3-formylbenzenesulfonyl chloride derivatives from the corresponding benzaldehydes has been developed. The key step in this procedure is the conversion of aldehyde bisulfite adducts to target compounds via a two-stage reaction in the presence of Na2SO4. A series of 3-formylbenzenesulfonyl chloride derivatives were prepared by this method and identified by chemical derivatization method. [ABSTRACT FROM AUTHOR]

A metal-free synthesis of 2-sulfonylindole derivatives has been developed through a novel TBHP/I2-mediated coupling of C3/unsubstituted indoles with sulfonyl hydrazides. The reaction utilizes readily available starting materials under mild reaction conditions, providing an alternative and attractive approach to 2-sulfonylindoles with high yields. The developed synthetic procedure is suitable for both N-protected or unprotected indoles. [ABSTRACT FROM AUTHOR]

A highly efficient synthesis of N-sulfonylamidines from N-sulfonyl-1,2,3-triazoles and amines is reported. This transformation undergoes silver-catalyzed or metal-free thermally promoted denitrogenation of N-sulfonyl-1,2,3-triazoles to afford N-sulfonylketenimine intermediates and subsequent nucleophilic addition with amines. The amine plays dual roles as base and nucleophile. [ABSTRACT FROM AUTHOR]

A facile and simple ligand-free copper-catalyzed reaction to synthesize substituted phenols is reported. The reaction presumably proceeds via an O-arylsulfonate intermediate that is hydrolyzed to afford good to excellent yields of up to 88%. This protocol provides an alternative to existing reports which use strong hydroxide salts as the direct hydroxylation partner. Demonstrating a wide substrate scope and functional group tolerance, this protocol can also be applied to inexpensive and commercially available carboxylic acids to yield phenols. [ABSTRACT FROM AUTHOR]

A protocol for the efficient conversion of sulfonyl fluorides into sulfonyl azides through Lewis base activation is described. The in situ generated sulfonyl azides are efficient diazo-transfer agents, affording diazo compounds and primary azides in excellent yields. [ABSTRACT FROM AUTHOR]

The first application of iron-catalyzed sulfonylation of aryl enol acetates with sulfonyl hydrazides for the construction of β-keto sulfones under aerobic conditions is reported. The present protocol, which utilizes an inexpensive iron salt as the catalyst, readily available sulfonyl hydrazides as the sulfonylating reagents, and air as oxidant under mild conditions, provides a cost-effective and environmentally benign approach to various β-keto sulfones. [ABSTRACT FROM AUTHOR]

A convenient synthesis of N-substituted heterocycles from primary and secondary alcohols and N-sulfonyl heterocycles is described. The reaction proceeds through sulfonyl transfer and in situ formation of activated alcohol derivatives. The formation of alkyl sulfonates as transient intermediates mitigates challenges associated with isolation of these reactive species. N-Sulfonyl heteroarenes were found to be stable over prolonged time, and efficiently coupled to a variety of alcohols. [ABSTRACT FROM AUTHOR]

The protecting-group-free total synthesis of (+)-clavulatriene A has been achieved. Key features of the synthetic strategy include the development of a novel strategy for the practical synthesis of a-cyperone, and a one-pot palladium-catalyzed reductive desulfonylation and deacetoxylation reaction. Furthermore, the total synthesis described in this study allowed for the determination of the absolute configuration of (+)-clavulatriene A. [ABSTRACT FROM AUTHOR]

Irreversible acid-nitrile exchange reactions using both glutaronitrile and (phenylsulfonyl)acetonitrile may be catalyzed by Lewis acids. Whereas a cyclization towards imides displaces the equilibria in the reaction with dinitriles, a decarboxylation step is involved when using the (phenylsulfonyl)acetonitrile. [ABSTRACT FROM AUTHOR]

Alkyl aryl ketones are converted into the corresponding a-sulfonyloxyketones, in moderate to excellent yields, via a novel procedure that utilizes Oxone®, p-toluenesulfonic acid or methanesulfonic acid and molecular iodine in a mixture of acetonitrile and 2,2,2-trifluoroethanol. The yield is found to be dependent on the nature of the ketone. A mechanism is proposed in which the key intermediates are an a-iodoketone and a subsequently formed a- iodosylketone. The latter reacts with the sulfonic acid to afford the a-sulfonyloxyketone product. [ABSTRACT FROM AUTHOR]

A variety of vinylallenes were successfully synthesized from 1-chlorovinyl p-tolyl sulfoxides and allyl or vinyl sulfones. Allyl and vinyl sulfones served as a-sulfonylallyllithium sources were prepared from carbonyl compounds in three or four steps in good overall yields. The coupling reaction of a-sulfonylallyllithi-ums with magnesium alkylidene carbenoids, which were generated from 1-chloro vinyl p-tolyl sulfoxides and isopropylmagnesium chloride, afforded multi-substituted vinylallenes in up to 88% yield. [ABSTRACT FROM AUTHOR]

Trimethylsilyl enol ethers bearing trialkylsilyl-protected hydroxy groups were converted into synthetically valuable bifunctional alkenyl nonaflates under the action of nonafluorobutane-1- sulfonyl fluoride combined with potassium fluoride in the presence of catalytic amounts of dibenzo-18-crown-6. The methodology has been demonstrated for structurally diverse substrates possessing various trialkylsilyl-protected hydroxy groups which remained intact during the reaction course. [ABSTRACT FROM AUTHOR]

Various carboxylic acids were converted into acyl fluorides in excellent yields by treatment with trichloroacetonitrile, triphenylphosphine, and TBAF(t-BuOH)4 at room temperature. The reaction was applicable to the preparation of acid-sensitive amino acid fluorides without deprotection or rearrangement. [ABSTRACT FROM AUTHOR]

1,2-Diarylanthraquinones were prepared by Suzuki-Miyaura reactions of the bis(triflate) of 1,2-dihydroxyanthraquin�one (alizarin). The reactions proceed with excellent site selectivity. The first attack occurs at the sterically more hindered position 1, due to electronic reasons. [ABSTRACT FROM AUTHOR]

Treatment of 1-chlorocyclobutyl p-tolyl sulfoxides with ethylmagnesium chloride at low temperature gave cyclobutylmagnesium carbenoids in over 90% yield. The generated magnesium carbenoids were found to be stable at -78 ˚C for at least 30 min. The synthesis of multisubstituted cyclobutanes and alkylidenecyclo�butanes was realized based on the alkylation of the magnesium carbenoids with Grignard reagent and lithium α-sulfonyl carbanions, respectively. [ABSTRACT FROM AUTHOR]

Synthesis of the eastern hemisphere (C1-C15) of pal�merolide A is described. A re-optimized Claisen-type condensation of vinylogous acyl triflates provides efficient entry into the C1-C8 subunit, setting up a convergent Horner-Wittig olefination to deliver the eastern portion of palmerolide A. [ABSTRACT FROM AUTHOR]

Hydrogen peroxide, in the presence of zirconium tetrachloride, is a very efficient reagent for the direct oxidative conversion of thiol and disulfide derivatives into the corresponding sulfonyl chlorides with high purity through oxidative chlorination. Excellent yields, very short reaction times, mild reaction conditions, and the avoidance of harsh reagents are the main advantages of this method. [ABSTRACT FROM AUTHOR]

Carbohydrate-based tolylsulfonyl hydrazines were used for the first time to catalyze the Michael reaction of indoles to electron-deficient olefins in aqueous media to afford 3-substituted indole derivatives in good to excellent yields at room temperature. [ABSTRACT FROM AUTHOR]

3-Arylsulfonyl pyrroles can be readily obtained from 3-Br-TIPS pyrrole via halogen-metal exchange and subsequent sulfonylation. The regioselectivity of the subsequent directed ortho-metallation (DOM) reaction in order to functionalise the C-2 position depends on the nature of the base (LTMP, n- or s-BuLi) and the N-substituent (SEM or Boc) used. The bulk of the N-substituent also strongly influences the yield of the subsequent Suzuki coupling with 2-iodo-3-arylsulfonyl pyrrole derivatives. [ABSTRACT FROM AUTHOR]

An α-deprotonation of carbonyl compounds with phos�phazene bases in the presence of the internal quenching reagent, nonafluorobutane-1-sulfonyl fluoride furnishes the corresponding alkenyl nonaflates. The new general method provides high yields of alkenyl nonaflates from aldehydes and cyclic ketones. However, it is not applicable to acyclic ketones whose nonaflate derivatives undergo fast E2 elimination to give alkynes. Successful synthesis of nonaflates from aldehydes requires carefully controlled reaction conditions to avoid the subsequent elimination to alkynes. A kinetic control enables high regioselectivities in favor of least substituted nonaflate regioisomers derived from cyclic ketones and modest Z-selectivities of alkenyl nonaflates derived from aldehydes. A new efficient protocol for highly selective removal of perfluorosulfolane admixture from technical nonafluorobutane-1-sulfonyl fluoride by basic hydrolysis is described. [ABSTRACT FROM AUTHOR]

N-Sulfonyl pyridinones derived from α-furylsulfon�amides may be aromatised with concomitant N→O sulfonyl transfer to produce 3-sulfonyloxypyridines. [ABSTRACT FROM AUTHOR]

Copper(II) triflate effectively catalyzes the reaction of (trimethylsilyloxy)acrylic esters and acetals to form γ-alkoxy-α-keto esters. The reaction proceeds under mild conditions providing products in good to excellent yields. The substrate scope was investigated, and it was demonstrated that the products could be converted into related compounds such as γ-hydroxy-α-keto esters and �α-oximes. [ABSTRACT FROM AUTHOR]

A simple synthesis of 2-imino-3-aminobenzofurans was developed based on multicomponent reactions from p-toluenesulfonylmethylisocyanide, salicylaldehyde, and substituted anilines. The crystal structures of two of the aminobenzofurans were established by X-ray crystal structure analysis. [ABSTRACT FROM AUTHOR]

The catalytic asymmetric synthesis of 3-substituted benzo-fused sultams employing the Corey-Bakshi-Shibata reduction with catecholborane of the corresponding cyclic N-sulfonylimines is reported. Good to excellent yields (74-95%) and enantiomeric excesses (69-94%) are obtained. [ABSTRACT FROM AUTHOR]

Using propiolic acid as one of the reacting components, a copper-catalyzed three-component reaction of sulfonyl azide and amines affords N-sulfonylacetamidines via a decarboxylation process in high yields under mild conditions. This one-pot method is efficient, general, and versatile. [ABSTRACT FROM AUTHOR]

The article describes the synthesis of β-hydroxy-α-substituted ketones through the stereocontrolled addition of Grignard reagents to α-epoxy N-sulfonyl hydrazones, a method created by the authors from the University of Houston in Texas. The opinion of professor Gregory B. Dudley about such method is presented. Coltart considers the method's generality as its most remarkable feature.

The article focuses on the Davis reagent, a chiral derivative of N-sulfonyl oxaziridine for various organic functional group transformations. It says that the reagent can be prepared through biphasic basic oxidation of N-benzylidene benzene-sulfonamide with oxone or m-chloropebenzoic acid (MCPBA). It also mentions that Davis reagent is essential for asymmetric functional group transformations due to stereoselective cleavage of the chirality and the weak nitrogen-oxygen (N-O) bond.

In this article, the author focuses on Bestmann-Ohira reagent which is a versatile reagent in organic synthesis. He mentions that the reagent can be prepared by the reaction of dimethyl-2- oxopropylphosphonate and further discusses how Bestmann-Ohira can be prepared through polymer-supported sulfonyl azide.