75421-89-5

Upstream product

• 10439-23-3 4-methylbenzenesulfinyl chloride 
• 109-97-7 pyrrole 
• 6873-87-6 N-butyl-4-methylbenzene-1-sulfinamide 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 87630-38-4 3-(p-tolylsulfinyl)-1-(triisopropylsilyl)pyrrole 
• 75421-80-6 2-(4-methylbenzenesufinyl)-1H-pyrrole 

Downstream Products

• 113976-59-3 1-Benzyl-2-chloro-3-(toluene-4-sulfinyl)-1H-pyrrole 
• 113976-57-1 2-Chloro-3-(toluene-4-sulfinyl)-1H-pyrrole 
• 98207-68-2 2-chloro-3-(p-tolylsulfonyl)pyrrole 
• 113976-55-9 2,5-dichloro-3-(p-tolylsulfonyl)pyrrole 
• 113976-52-6 1-benzyl-3-(p-tolylsulfinyl)-1H-pyrrole 

Relevant academic research and scientific papers

Efficient Synthesis of 3-(Arenesulfinyl)indoles in Water

Abstract: The first example of the sulfinylation of indoles with arylsulfinamides in water in the presence of trifluoroacetic acid as a promoter is described. The reaction occurs smoothly at room temperature under environmentally benign conditions without any catalyst, additive, ligand, or organic solvent. The developed sulfoxide synthetic protocol is attractive due to the use of water as the solvent and provides a novel and efficient route to a wide range of functionalized diaryl sulfoxides.

TMSOTf-Promoted Sulfinylation of Electron-Rich Aromatics with Sodium Arylsulfinates

A new transition-metal-free route for the direct sulfinylation of electron-rich aromatics with sodium arylsulfinates in the presence of TMSOTf is reported. Various electron-rich aromatics, including pyrroles, thiophenes, indoles, and electron-rich arenes, with sodium arylsulfinates are converted into the corresponding sulfoxides in moderate to excellent yields. This protocol possesses many advantages such as readily available and stable starting materials, broad substrate scopes, and transition-metal-free reaction conditions.

Regioselective and oxidant-free sulfinylation of indoles and pyrroles with sulfinamides

An unexpected time-controlled highly selective C3-or C2-sulfinylation of pyrroles with sulfinamides is reported for the first time. The sulfinylation of indoles with sulfinamides using this protocol is oxidant-free and can be performed under obviously more feasible conditions (1.2 equiv. of indoles, 10 min) in comparison with the precedent procedure (3-20 equiv. of indoles, 16-18 h, ammonium persulfate as oxidant, hv). A variety of functional groups were tolerated, and various C2-thioindoles and C2/3-thiopyrroles were obtained in moderate to excellent yields.

N-(Triisopropylsilyl)pyrrole. A Progenitor "Par Excellence" of 3-Substituted Pyrroles

A very effective strategy has been devised for the synthesis of 3-substituted pyrroles based on the use of the triisopropylsilyl (TIPS) moiety as a sterically demanding nitrogen substituent to obstruct the attack of electrophilic reagents at the α positions. 1-(Triisopropylsilyl)pyrrole (1) undergoes highly preferential kinetic electrophilic substitution at the β position with a variety of electrophiles (Br+, I+, NO2+, RCO+, etc.) and fluoride ion induced desilylation of the products provides the corresponding 3-substituted pyrroles in good overall yields.Competitive trifluoroacetylation experiments demonstrate that substitution of TIPS-pyrrole at the α positions is decelerated by a factor of >104, vs pyrrole at the same sites, without affecting reactivity at the β positions. 1-(Triisopropylsilyl)-3-bromopyrrole (2) is readily converted into the 3-lithio compound 44 by bromine-lithium interchange with alkyllithium reagents.This previously unavailable, formal equivalent of 3-lithiopyrrole is itself an excellent source of a wide range of β-substituted pyrroles, many of which would not be directly preparable from 1.TIPS-pyrrole can be 3,4-dihalogenated and these compounds undergo sequential halogen-metal interchange trapping reactions.This process is exemplified by an efficient, three-step synthesis of the antibiotic verrucarin E (63) from the dibromo compound (5).

THE TOTAL SYNTHESIS OF (+/-)-ISORETRONECANOL FROM PYRROLE

A total synthesis of (+/-)-isoretronecanol from pyrrole is described which uses several novel pyrrole reactions including an intramolecular nucleophilic displacement reaction on a toluenesulfonyl-activated pyrrole followed by reductive removal of the acti

β-SUBSTITUTED PYRROLES VIA ELECTROPHILIC SUBSTITUTION OF N-TRIISOPROPYLSILYLPYRROLE

N-Triisopropylsilylpyrrole undergoes predominant or exclusive kinetic electrophilic substitution at C-3, and the compounds obtained thereby, upon desilylation with tetra-n-butylammonium fluoride, give 3-substituted pyrroles in good overall yields.

Synthesis and Rearrangement of 2-(Arylsulfinyl)- and 2-(Alkylsulfinyl)pyrroles

Pyrrole and N-methylpyrrole reacted with aryl- and alkylsulfinyl chlorides, at 0 deg C, to give the corresponding 2-sulfinylpyrroles as the major products only when contact of the products with the liberated hydrogen chloride was minimized or eliminated.If this precaution was not taken, the 3-sulfinylpyrroles were the principle products.In contrast, N-(phenylsulfinyl)succinimide (2a) reacted, at room temperature, with a variety of pyrroles to produce the 2-phenylsulfinyl compounds in good yields.The 2-(arylsulfinyl)- and 2-(alkylsulfinyl)pyrroles undergo a remarkably facile acid-promoted rearrangement to the isomeric 3-sulfinylpyrroles.This transposition is, at least in part, an intermolecular process as demonstrated by crossover experiments.