98598-96-0

Upstream product

• 95-20-5 2-methyl-1H-indole 
• 6627-89-0 tert-butyl phenyl carbonate 
• 27826-16-0 sodium salt of 2-methylindole 
• 129822-51-1 [2-(2-Oxo-propyl)-phenyl]-carbamic acid tert-butyl ester 
• 496043-83-5 2-[2'-(N-Boc-N-trimethylsilyl-amino)phenyl]-1,3-dithiane 
• 490035-94-4 tert-butyl N-[2-(1-methylethenyl)phenyl]carbamate 
• 74965-31-4 N-(tert-butoxycarbonyl)-o-toluidine 
• 552-89-6 2-nitro-benzaldehyde 
• 496043-66-4 2-[2'-(N-Boc-amino)-5'-chlorophenyl]-1,3-dithiane 
• 396094-78-3 2-[2'-(N-Boc-amino)phenyl]-1,3-dithiane 
• 111253-51-1 1-chloro-3-<(1,3-dithian)-2'-yl>-4-nitrobenzene 
• 35531-58-9 2-(2-nitrophenyl)-1,3-dithiane 
• 6628-86-0 5-chloro-2-nitrobenzaldehyde 
• 53165-23-4 2-(2'-amino-5'-chlorophenyl)-1,3-dithiane 

Relevant academic research and scientific papers

Enantioselective Construction of Dihydropyrido[1,2- a]indoles via Organocatalytic Arylmethylation of 2-Enals with Inert Aryl Methane Nucleophiles

An organocatalytic asymmetric arylmethylation/N-hemiacetalization of 2-indolyl methane derivatives and 2-enals was developed. Notably, the 2-methyl of indole was readily deprotonated to produce highly reactive nucleophilic species by introducing the nitro

Selectivity control in gold-catalyzed hydroarylation of alkynes with indoles: Application to unsymmetrical bis(indolyl)methanes

Gold-catalyzed hydroarylation of unactivated alkynes with indoles have previously been reported to proceed with double indole addition to produce symmetrical bis(indolyl)methanes (BIMs). We demonstrate for the first time that the selectivity of the gold-c

Sensitive Assays by Nucleophile-Induced Rearrangement of Photoactivated Diarylethenes

Upon light-induced isomerization, diarylethenes (DAEs) equipped with reactive aldehyde moieties rearrange selectively in the presence of amines, accompanied by decoloration. In a comprehensive study, the probe structure was optimized with regard to its inherent reactivity in the nucleophile-triggered rearrangement reaction. Detailed structure-reactivity relationships could be derived, in particular with regard to the type of integrated (het)aryl moieties as well as the location of the formyl residue, and the probes' intrinsic reactivity with primary and secondary amines was optimized. Utilizing an ancillary base, the initially formed rearrangement product can engage in a subsequent catalytic cycle, leading to an amplified decoloration process. This additional catalytic pathway allows us to enhance the sensitivity of our method and successfully discriminate between amines and thiols. Moreover, probes that exhibit strong analyte-induced fluorescence modulation have been designed to further decrease the detection limit by using a more sensitive read-out. The optimized DAE probes are promising molecular components for future programmable sensing materials and devices.

Fluorine as a Traceless Directing Group for the Regiodivergent Synthesis of Indoles and Tryptophans

Despite ample evidence for the unique reactivity offered by hypervalent F-iodanes, mechanistic investigations fall far behind. In order to shed light on the unusual behavior of such F-reagents, we conducted computational and experimental studies on the chemodivergent transformation of styrenes. We identified the spirocyclic F-cyclopropane as the common intermediate for both the C,H-fluorination and C,H-amination pathways. The fate of this key compound is determined by the extent of cationic charge delocalization controlled by the N-substituents. Exploiting this phenomenon, a multitude of different transformations have become available, leading, i.e., to the regiodivergent synthesis of indoles and tryptophans.

Palladium-catalyzed diastereoselective oxyarylation of 2-alkylindoles

Diastereoselective oxyarylation of N-protected 2-alkylindoles with commercially available boronic acids and TEMPO as a mild oxidant to give N-protected 2-aryl-2-alkyl-3-(2-chloroacetoxy)indolines is described. Reactions are easy to conduct, and product indolines containing a fully substituted C-center are obtained in good yields with good to excellent selectivities.

A trans diacyloxylation of indoles

A trans diacyloxylation of indoles is accomplished by employing PhI(OAc)2 as the oxidant. A broad range of functional groups are well tolerated. Both the electronic properties of the N-protecting groups of indoles and the acidity of the reaction media play important roles in the selectivity of indole acyloxylation reactions. The Royal Society of Chemistry 2012.

Efficient N-tert-butoxycarbonylation of indoles with di-tert-butyl dicarbonate catalyzed by cesium fluoride

An environmentally friendly process for the tert-butoxycarbonylation of indoles with di-tert-butyl dicarbonate has been developed. Catalytic amount of cesium fluoride can accelerate this tert-butoxycarbonylation. Georg Thieme Verlag Stuttgart.

Ruthenium-catalyzed asymmetric hydrogenation of N-Boc-indoles

Highly enantioselective hydrogenation of various N-Boc-indoles proceeded successfully in the presence of the ruthenium complex generated from an appropriate ruthenium precursor and a trans-chelate chiral bisphosphine PhTRAP. Various 2- or 3-substituted indoles were converted into chiral indolines with high enantiomeric excesses (up to 95% ee). The PhTRAP-ruthenium catalyst was able to promote the hydrogenation of 2,3-dimethylindoles, giving cis-2,3-dimethylindolines with 72% ee.

Synthesis of 2-substituted benzofurans and indoles using functionalized titanium benzylidene reagents on solid phase

Titanium(IV) benzylidenes bearing a masked oxygen or nitrogen nucleophile in the ortho position were generated from thioacetals, using low-valent titanocene complex, Cp2Ti[P(OEt)3]2. Methylene acetal, alkyl ether, silyl ether, fluoro, tertiary amino, and N-alkyl, N-benzyl, N-prenyl, and N-silyl tert-butyl carbamate groups were tolerated in the titanium alkylidene reagents (Schrock carbenes). Aryl-chlorine bonds were stable to the titanium benzylidene functionality, but there was poor chemoselectivity for the reduction of the thioacetal in the presence of an aryl chloride. The titanium benzylidenes converted Merrifield and Wang resin-bound esters into enol ethers. The oxygen nucleophile was masked as a TMS ether, and when the resin-bound enol ethers bearing this ortho substituent were treated with 1% TFA in dichloromethane, benzofurans were released from resin in high yields. The chameleon catch strategy ensured excellent purity. In a similar way, N-alkylated and N-silylated tert-butyl carbamates were used for the synthesis of N-alkyl and N-Boc indoles, respectively. These traceless solid-phase syntheses of heterocycles are believed to involve post-cleavage modification rather than cyclative termination.

Novel functionalized titanium(IV) benzylidenes for the traceless solid-phase synthesis of indoles

(matrix presented) Titanium(IV) benzylidenes bearing a masked nitrogen nucleophile in the ortho position converted Merrifield resin-bound esters into enol ethers. An unusual nitrogen protecting group, N-silylated tert-butyl carbamate, was employed. One percent TFA released N-Boc indoles in high yield and purity. N-Methyl indoles were also prepared. Cyclative termination was not required to release the chameleon catch. The first example of a carbonyl group within a titanium alkylidene reagent is reported.