Arylsulfonyl Hydrazides Research Articles

ChemInform Abstract: Iodine‐Mediated Synthesis of Aromatic Thioethers with Aromatic Amines and Sulfonyl Hydrazides in High Regioselectivity via C(sp2)—H Bond Functionalization.

AbstractA convenient synthesis of bis(aryl) thioethers having a para‐amino substituent is rendered possible by a highly regioselective oxidative C—H coupling of N,N‐disubstituted anilines with arylsulfonyl hydrazides.

ChemInform Abstract: A New Cascade Halosulfonylation of 1,7‐Enynes Toward 3,4‐Dihydroquinolin‐2(1H)‐ones via Sulfonyl Radical‐Triggered Addition/6‐exo‐dig Cyclization.

AbstractThe title synthesis follows a α,β‐conjugated addition/6‐oxo‐dig cyclization/radical coupling sequence.

Catalytic Diazosulfonylation of Enynals toward Diazoindenes via Oxidative Radical-Triggered 5-exo-trig Carbocyclizations.

Catalytic diazosulfonylation of enynals with arylsulfonyl hydrazides has been established by using tert-butyl hydroperoxide (TBHP) as the oxidant with tetrabutylammonium iodide (TBAI) under a convenient system. The reaction occurred through oxidative radical-triggered 5-exo-trig carbocyclization cascading to afford sulfonylated diazoindenes regioselectively. The new diazosulfonylation reaction features a broad substrate scope, readily accessible starting materials, and a simple one-pot process.

NH4I‐Catalyzed Synthesis of Sulfonamides from Arylsufonylhydrazides and Amines

AbstractA novel and efficient approach to sulfonamides has been developed. Using TBHP as the oxidant and NH4I (20 mol%) as the catalyst, arylsulfonyl hydrazides reacted with amines to provide sulfonamides in moderate to good yields. Possible reaction pathway for the formation of the products was also discussed in this paper.

ChemInform Abstract: AlCl3‐Promoted Thiolation of Acyl C—H Bonds with Arylsulfonyl Hydrazides.

Abstract AlCl3-promoted thiolation of acyl C–H bonds with arylsulfonyl hydrazides was developed, which represents an effective synthesis of S-aryl thiocarbamates via C–S bond formation reaction.

Palladium-catalyzed direct arylation of indoles with arylsulfonyl hydrazides.

A novel method to synthesise 2-arylindoles is demonstrated via direct arylation of indoles with arylsulfonyl hydrazides. Under the optimized reaction conditions, the reaction well tolerates a wide variety of functional groups to afford structurally diverse 2-arylindoles in good to excellent yields at 70 °C.

Palladium-catalyzed N-arylsulfonamide formation from arylsulfonyl hydrazides and nitroarenes

Various N-arylsulfonamides were prepared from nitroarenes and arylsulfonyl hydrazides via hydrogen transfer methodology.

Palladium-catalyzed C-3 desulfitative arylation of indolizines with sodium arylsulfinates and arylsulfonyl hydrazides

Derivatized indolizines were efficiently prepared by direct C-3 arylation of indolizines using sodium arylsulfinates and arylsulfonyl hydrazides in good yields.

Iodine-catalyzed expeditious synthesis of sulfonamides from sulfonyl hydrazides and amines.

A new synthesis of sulfonamides has been developed via an iodine-catalyzed sulfonylation of amines with arylsulfonyl hydrazides. This metal-free strategy employs readily accessible and easy to handle starting materials, catalysts and oxidants, and can be easily conducted under mild conditions, providing a convenient access to a wide range of sulfonamides in moderate to excellent yields within a short reaction time.

CeCl3⋅7H2O‐NaI Promoted Regioselective Sulfenylation of Indoles with Sulfonylhydrazides

AbstractA simple and highly efficient method has been developed for the regioselective sulfenylation of a wide variety of indoles with alkyl and aryl sulfonylhydrazides as a sulphur source and CeCl3⋅7H2O‐NaI as an inexpensive and readily available reagent system. This method involves the breaking of sulfur–oxygen and sulfur–nitrogen bonds and making of carbon‐sulfur bond. The method provides high yields of the products with enhanced regioselectivity. We studied the reactivity of various electron rich and electron deficient indoles towards the sulfenylation reaction. The indoles containing electron donating group reacts fast towards the sulfenylation reaction as compared to the indoles containing electron withdrawing groups. More over functional groups like alkoxy, aryloxy, bromo, nitro, cyano, ester, were well tolerated under the established reaction conditions. We also proposed a plausible mechanism for this transformation. The experimental simplicity and environmentally benign nature of the reagent system makes this method an attractive alternative to established methods.

A new cascade halosulfonylation of 1,7-enynes toward 3,4-dihydroquinolin-2(1H)-ones via sulfonyl radical-triggered addition/6-exo-dig cyclization.

A new cascade three-component halosulfonylation of 1,7-enynes for efficient synthesis of densely functionalized 3,4-dihydroquinolin-2(1H)-ones has been established from readily accessible arylsulfonyl hydrazides and NIS (or NBS). The reaction pathway involves in situ-generated sulfonyl radical-triggered α,β-conjugated addition/6-exo-dig cyclization/radical coupling sequence, resulting in continuous multiple bond-forming events including C-S, C-C and C-I (or C-Br) bonds to rapidly build up molecular complexity.

Open-air oxidative Mizoroki–Heck reaction of arylsulfonyl hydrazides with alkenes

A palladium(ii)-catalyzed oxidative Mizoroki–Heck reaction of arylsulfonyl hydrazides with alkenes was developed employing Pd(OAc)2 and pyridine ligand L9 as a catalyst system and ​atmospheric air as the sole oxidant in an open-vessel manner.

AlCl3-promoted thiolation of acyl C–H bonds with arylsulfonyl hydrazides

AlCl3-promoted thiolation of acyl C–H bonds with arylsulfonyl hydrazides was developed, which represents an effective synthesis of S-aryl thiocarbamates via C–S bond formation reaction.

Metal-Free Iodine-Catalyzed Synthesis of Fully Substituted Pyrazoles and Its Sulphenylation.

A direct and metal-free access toward fully substituted pyrazoles and its sulphenylation has been established through an iodine-mediated three-component [3 + 2] annulation of β-ketonitrile (or pentane-2,4-dione), arylhydrazines, and aryl sulfonyl hydrazides. The reaction allows the formation of one C-S and two C-N bonds by the multiple bond cleavage including sulfur-oxygen, sulfur-nitrogen, and carbon-oxygen bonds. The method features low-cost and readily accessible substrates, bond-forming efficiency, and broad substrate scopes as well as simple one-pot operation, which makes this strategy highly attractive.

ChemInform Abstract: Nickel‐Catalyzed C—S Bond Formation: Synthesis of Aryl Sulfides from Arylsulfonyl Hydrazides and Boronic Acids.

AbstractThioethers are prepared by cross—coupling of arylsulfonyl hydrazides and aryl boronic acids using a nickel catalyst.

ChemInform Abstract: Palladium‐Catalyzed Hiyama Coupling Reaction of Arylsulfonyl Hydrazides under Oxygen.

AbstractThe Hiyama‐coupling of arylsulfonyl hydrazides with aryl silanes as an alternative aproach to the coupling of silanes with aryl halides is reported.

A Direct Metal-Free Decarboxylative Sulfono Functionalization (DSF) of Cinnamic Acids to α,β-Unsaturated Phenyl Sulfones.

A metal-free room temperature decarboxylative cross-coupling between cinnamic acids and arylsulfonyl hydrazides has been realized for the first time for the synthesis of (E)-vinyl sulfones. The scope and versatility of the reaction has been demonstrated by the regio- and stereoselective synthesis of 22 derivatives with diverse structural features.

ChemInform Abstract: Iodine‐Mediated Thiolation of Substituted Naphthols/Naphthylamines and Arylsulfonyl Hydrazides via C(sp2)—H Bond Functionalization.

A direct method has been developed for iodine-mediated thiolation of naphthols/naphthylamines and arylsulfonyl hydrazides through the formation of C-S bond and cleavage of S-N/S-O bonds. In this transformation, a range of valuable thioethers are easily achieved in moderate to good yields.

Nickel‐Catalyzed CS Bond Formation: Synthesis of Aryl Sulfides from Arylsulfonyl Hydrazides and Boronic Acids

AbstractA practical nickel‐catalysed approach has been developed for the CS bond formation through the cross‐coupling of arylsulfonyl hydrazides and aryl boronic acids. The report employs arylsulfonyl hydrazide as an aryl thiol equivalent and offers a mild and eco‐safe synthesis of unsymmetrical thioethers in good to excellent yields in air. The scope and versatility of the method has been successfully demonstrated with 22 examples.magnified image

ChemInform Abstract: p‐Toluenesulfonic Acid‐Promoted, I2‐Catalyzed Sulfenylation of Pyrazolones with Aryl Sulfonyl Hydrazides.

AbstractThe I2‐catalyzed cross‐coupling of pyrazolones with aryl sulfonyl hydrazides furnishes aryl pyrazolone thioethers.