129822-50-0

Upstream product

• 1504-16-1 3-phenyl-1H-indole 
• 24424-99-5 di-tert-butyl dicarbonate 
• 1428541-15-4 (E)-styryl(o-tolyl)-λ³-iodanyl trifluoromethanesulfonate 
• 58377-40-5 tert-butyl N-hydroxy-N-phenylcarbamate 
• 161117-84-6 tert-butyl 2-iodophenylcarbamate 
• 1448535-75-8 (E)-tert-butyl 2-iodophenyl(styryl)carbamate 
• 1448535-66-7 tert-butyl 2-iodophenyl(2-phenylacetyl)carbamate 
• 103-80-0 phenylacetyl chloride 
• 1440671-87-3 N-(2-bromophenyl)-N-tert-butoxycarbonyl-phenylethynylamine 
• 536-74-3 phenylacetylene 
• 932-87-6 1-Bromo-2-phenylacetylene 
• 129822-44-2 (2-Benzyl-phenyl)-carbamic acid tert-butyl ester 
• 28059-64-5 2-benzylaniline 
• 138344-46-4 2-Hydroxy-3-phenyl-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester 

Relevant academic research and scientific papers

Copper-Catalyzed Tandem O-Vinylation of Arylhydroxylamines/[3,3]-Rearrangement/Cyclization: Synthesis of Highly Substituted Indoles and Benzoindoles

Herein, we developed a copper-catalyzed O-vinylation of arylhydroxylamine using vinyliodonium salts as vinylation reagents to generate a transient O-vinyl-N-arylhydroxylamine that rapidly undergoes a [3,3]-sigmatropic rearrangement and subsequent cyclizat

Microwave-assisted synthesis of 3-substituted indoles via intramolecular arene-alkene coupling of o-iodoanilino enamines

A generally applicable and high-yielding protocol for the synthesis of 3-substituted indole derivatives is described. Key features include microwave-assisted intramolecular arene-alkene coupling of o-iodoanilino enamines, and expedient synthesis of o-iodo

Intramolecular carbocupration of N-aryl-ynamides: A modular indole synthesis

A modular indole synthesis based on an intramolecular 5-endo-dig carbocupration starting from readily available N-aryl-ynamides is reported. A variety of ynamides are converted to indoles in moderate to good yields and with varying substitution pattern on the indole ring. This further extends the synthetic utility of ynamides in organic synthesis and provides additional insights on the use of intramolecular carbometalation reactions.

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.

Preparation of indoles and oxindoles from N-(tert-butoxycarbonyl)-2-alkylanilines

Treatment of dilithiated N-(tert-butoxycarbonyl)anilines 1 with dimethylformamide or carbon dioxide furnishes intermediates 3, 5, that are easily converted to N-(tert-butoxycarbonyl)indoles 4 and oxindoles (indol-2(3H)-ones, 7), respectively. Condensation of dilithiated 1 with N-methoxy-N-methylamides provides ketones 9 which are cyclized upon trifluoroacetic acid treatment to either 2-substituted 1-(tert-butoxycarbonyl)indoles 10 or 2-substituted indoles 11 depending on the reaction time. This general methodology has been applied to efficient synthesis of 1,2-alkyl-bridged indoles 12, 1,3,4,5-tetrahydrobenz[c,d]indole (16), 2a,3,4,5-tetrahydrobenz[c,d]indol-2(1H)-one (18), and 1-(tert-butoxycarbonyl)1H-pyrrolo[2,3-b]pyridine (21).