72496-78-7

Upstream product

• 120-72-9 indole 
• 7669-54-7 2-nitrobenzenesulfenyl chloride 
• 1155-00-6 bis(2-nitrophenyl)disulfide 
• 22057-44-9 1-(benzylsulfanyl)-2-nitrobenzene 
• 5906-99-0 2-nitrobenzenesulfonyl hydrazide 
• 88-73-3 2-Chloronitrobenzene 
• 1694-92-4 2-Nitrobenzenesulfonyl chloride 
• 609-73-4 o-nitroiodobenzene 
• 17356-08-0 thiourea 
• 15898-45-0 sodium 2-nitrobenzenesulfinate 
• 13165-79-2 2-nitrobenzenesulfinic acid 

Downstream Products

• 32884-72-3 indol-3-yl o-aminophenyl sulphide 
• 120105-59-1 3’H-spiro[indole-3,2’-[1,3]]benzothiazole-2(1H)-one 

Relevant academic research and scientific papers

Recyclable Cellulose-Derived Fe3O4@Pd NPs for Highly Selective C–S Formation by Heterogeneously C–H Sulfenylation of Indoles

Abstract: An efficient and convenient method was developed for the preparation of 3-sulfenylindoles via a cellulose-derived Fe3O4@Pd NPs catalyzed heterogeneously C–H sulfenylation of indoles. This approach provides an effective synthetic route to an important class of indoles derivatives and features high efficiency, easy operation, good practicality, and environmental friendliness. The recoverable catalyst was separated from the reaction mixture using an outside magnetic field and can be recycled five times without huge loss of catalytic performance. Graphic Abstract: An efficient method was developed for the preparation of 3-sulfenylindoles via cellulose-derived Fe3O4@Pd NPs catalyzed heterogeneously C–H sulfenylation of indoles.[Figure not available: see fulltext.].

Organophosphorus-Catalyzed Deoxygenation of Sulfonyl Chlorides: Electrophilic (Fluoroalkyl)sulfenylation by PIII/PV=O Redox Cycling

A method for electrophilic sulfenylation by organophosphorus-catalyzed deoxygenative O-atom transfer from sulfonyl chlorides is reported. This C?S bond-forming reaction is catalyzed by a readily available small-ring phosphine (phosphetane) in conjunction with a hydrosilane terminal reductant to afford a general entry to sulfenyl electrophiles, including valuable trifluoromethyl, perfluoroalkyl, and heteroaryl derivatives that are otherwise difficult to access. Mechanistic investigations indicate that the twofold deoxygenation of the sulfonyl substrate proceeds by the intervention of an off-cycle resting state thiophosphonium ion. The catalytic method represents an operationally simple protocol using a stable phosphine oxide as a precatalyst and exhibits broad functional-group tolerance.

Synthesis of a new series of Ni(II), Cu(II), Co(II) and Pd(II) complexes with an ONS donor Schiff base: Crystal structure, DFT study and catalytic investigation of palladium and nickel complexes towards deacylative sulfenylation of active methylenes and regioselective 3-sulfenylation of indoles: Via thiouronium salt formation

A series of Ni(ii), Cu(ii), Co(ii), and Pd(ii) complexes have been synthesized with a chelating Schiff base ligand coordinated to a metal center with ONS donor atoms. The ligand and complexes are characterized by elemental analysis and spectroscopic techniques like FT-IR, 1H-NMR, and UV-Visible spectroscopy. The single crystal structure of the Pd(ii) complex is obtained by X-ray diffraction analysis and exhibits slightly distorted square planar geometry. The structure is optimized by DFT, TD-DFT calculation to elaborate the electronic structure and NBO for the charge distribution analysis of the Pd(ii) complex. The synthesized Pd(ii) and Ni(ii) complexes as catalysts have been investigated in the C-S cross-coupling of indoles and active methylenes. The metal propelled regioselective transformation afforded 3-sulfenylated indoles while β-diketones favored deacylated monosulfenyl ketones in an excellent yield via thiouronium salt formation. The Pd(ii) complex displays slightly better reactivity whereas the Ni(ii) complex is cost-efficient. The method is fast, easy to handle and cost effective in terms of high reactivity of catalysts, use of non-toxic solvents, and cheaper aryl halides and thiourea replace conventional sulfur sources, providing a practical access to organic transformations.

Iodine-Catalyzed Mono- and Disulfenylation of Indoles in PEG400 through a Facile Microwave-Assisted Process

An iodine-catalyzed versatile and green method for the synthesis of mono- and 2,3-disulfenylindoles was developed. Various indoles reacted with sodium alkyl- and arylsulfinates by using hydrogen peroxide as the oxidizing agent in PEG400 under microwave conditions. This simple method enabled the rapid synthesis of mono- and 2,3-disulfenylindoles in good to excellent yields under metal-free conditions. Furthermore, this protocol is environmentally friendly, odorless, and operationally easy and can be performed within short reaction times under mild reaction conditions with excellent functional-group tolerance.

Microwave-assisted synthesis of 3-sulfenylindoles by sulfonyl hydrazides using organic ionic base-Br?nsted acid

A novel, efficient, and high-yielding method was developed for the synthesis of 3-sulfenylindoles via a DBU-based ionic liquid promoted sulfenylation of indoles using sulfonyl hydrazides as a thiol surrogate. The environmentally friendly procedure, easy operation and mild reaction conditions enable the tolerance of a wide scope of functionalities as well as high reaction efficiency. The synthetic procedure is suitable for both N-protected or unprotected indoles.

Microwave-assisted regioselective sulfenylation of indoles under solvent- and metal-free conditions

Herein, we report a solvent- and metal-free methodology for the sulfenylation of indoles with sulfinic acids in the absence of an external catalyst under microwave irradiation. This environmentally friendly approach offered the desired products in moderate to excellent yields in only 10 min. Several functional group tolerances were monitored under the optimized conditions.

Metal free sulfenylation of active methylene compounds and indole: TBATB mediated synthesis

The present work addresses a development of metal free one pot direct method for sulfenylation of active methylene compounds and indole. The reaction might proceed through sulfenyl bromide as an intermediate, which initiates the C-S bond formation. The re

TBATB mediated debenzylative cross-coupling of aryl benzyl sulfides with electron rich compounds: Synthesis of diaryl sulfides

An efficient TBATB mediated debenzylative cross coupling of aryl benzyl sulfides with electron rich compounds provides diaryl sulfides in moderate to excellent yield. The salient features of the present protocol are simplicity, high efficiency and compati

Silver ion mediated in situ synthesis of mixed diaryl sulfides from diaryl disulfides

The AgNO3-mediated in situ scission of aromatic disulfides in the presence of electron-rich aromatic compounds results in the efficient synthesis of diaryl sulfides. Key features of this new methodology are high yields of aromatic and heteroaromatic sulfides, mild reaction conditions, simplicity, simple workup, and avoiding foul-smelling reactants like thiols. Georg Thieme Verlag Stuttgart · New York.