36004-72-5

Upstream product

• 67-56-1 methanol 
• 201230-82-2 carbon monoxide 
• 1072943-52-2 N-[2-(2,2-dibromovinyl)phenyl]-4-methylbenzenesulfonamide 
• 1202-04-6 indole-2-carboxylic acid methyl ester 
• 98-59-9 p-toluenesulfonyl chloride 
• 945862-20-4 C₁₇H₁₇NO₄S 
• 100-63-0 phenylhydrazine 
• 71466-92-7 methyl 2-(phenylhydrazono)propionate 

Downstream Products

• 1202-04-6 indole-2-carboxylic acid methyl ester 
• 1378332-42-3 2-(fluoromethyl)-1-tosylindole 
• 1039186-86-1 2-morpholin-4-ylmethyl-1-(toluene-4-sulfonyl)-1H-indole 

Relevant academic research and scientific papers

Stereospecific Electrophilic Fluorocyclization of α,β-Unsaturated Amides with Selectfluor

An efficient fluorocyclization of α,β-unsaturated amides through a formal halocyclization process is developed. The reaction proceeds under transition-metal-free conditions and leads to the formation of fluorinated oxazolidine-2,4-diones with excellent regio- and diastereoselectivity. The evaluation of the reaction mechanism based on preliminary experiments and density functional theory calculations suggests that a synergetic syn-oxo-fluorination occurs and is followed by an anti-oxo substitution reaction. The reaction opens a new window in the field of stereospecific fluorofunctionalization.

Aerobic copper-catalyzed decarboxylative thiolation

Copper-catalyzed decarboxylative thiolation using molecular oxygen as the sole oxidant was developed. A variety of aromatic carboxylic acids including 2-nitrobenzoic acids, pentafluorobenzoic acid and several heteroaromatic carboxylic acids undergo efficient thiolation to furnish the aryl sulfides in moderate to excellent yields.

Unusual 1,2-aryl migration in Pd(II)-catalyzed aza-Wacker-type cyclization of 2-alkenylanilines

Inspired by the Hegedus aza-Wacker indole synthesis, we were intrigued with the fate of the aminopalladation intermediate if syn β-hydrogen is made inaccessible or unavailable. In contrast to our previously reported β-carbon elimination, cyclization of a

Palladium-catalyzed substitution and cross-coupling of benzylic fluorides

Benzylic fluorides are suitable substrates for Pd(0)-catalyzed Tsuji-Trost substitution using carbon, nitrogen, oxygen, and sulfur nucleophiles and for cross-coupling with phenylboronic acid. For the bifunctional substrate 4-chlorobenzyl fluoride, fine-tuning of the reaction conditions allows for the regioselective displacement of either the chlorine or fluorine substituent. The leaving group ability of fluoride vs other groups displaced in substitution is CF3CO2 ≈ p-NO2C6H 4CO2 ≈ OCO2CH3 > F > CH3CO2, a ranking similar to allylic fluorides under Pd catalysis.

Total synthesis of (+)-isatisine A

(Figure Presented) Isatis indigotica has long been used as a source of therapeutic compounds in traditional Chinese medicine (the roots are the source of Ben Lan Gen herbal tea). In 2007 the leaves of J. indigotica yielded isatisine A, an unusual oxidized bisindole. A concise, enantiospecific total synthesis of isatisine A is reported using a homochiral cyclopropane diester to construct the key tetrahydrofuran ring.

Total synthesis of (+)-isatisine A

The asymmetric total synthesis of (+)-isatisine A has been accomplished commencing with a Lewis acid-catalyzed cyclization of homochiral (S)-vinylcyclopropane diester and N-tosylindole-2-carboxaldehyde to construct the tetrahydrofuran ring. A palladium-ca

Tandem palladium-catalyzed N,C-coupling/carbonylation sequence for the synthesis of 2-carboxyindoles

(Chemical Equation Presented) Tandem palladium-catalyzed N,C-coupling/carbonylation, under 10 aim of carbon monoxide and at 110 °C, is a novel and efficient method for the preparation of 2-carboxyindoles. The catalyst system tolerates a variety of functional groups, and the noted indoles were obtained in good isolated yields.

Comparison of the reactivity between 2- and 3-nitropyrroles in cycloaddition reactions. A simple indole synthesis

N-Tosyl-2-nitropyrroles react at high temperature with poorly and strongly activated dienes. They exhibit a dienophilic character similar to N-tosyl-3-nitropyrroles producing the corresponding indoles through a classical Diels-Alder process. A similar beh