78388-92-8

Upstream product

• 673-32-5 1-Phenylprop-1-yne 
• 19591-17-4 o-iodoacetanilide 
• 23543-66-0 N-acetyl-3-methylindole 
• 71-43-2 benzene 
• 10257-92-8 2-phenyl-3-methyl-1H-indole 
• 75-36-5 acetyl chloride 
• 62-53-3 aniline 
• 98-95-3 nitrobenzene 
• 32954-65-7 N,O-diacetylphenylhydroxylamine 
• 1795-83-1 N-Phenylacetohydroxamic acid 
• 103-84-4 Acetanilid 
• 615-43-0 2-iodophenylamine 

Downstream Products

• 137449-25-3 1-ethyl-3-methyl-2-phenyl-1H-indole 
• 96569-40-3 1-acetyl-2,3-dihydroxy-3-methyl-2-phenylindoline 
• 10257-92-8 2-phenyl-3-methyl-1H-indole 

Relevant academic research and scientific papers

Easy Access to Versatile Catalytic Systems for C?H Activation and Reductive Amination Based on Tetrahydrofluorenyl Rhodium(III) Complexes

On the basis of the 1,2,3,4-tetrahydrofluorenyl ligand, a simple approach was developed to new effective rhodium catalysts for the construction of C?C and C?N bonds. The halide compounds [(η5-tetrahydrofluorenyl)RhX2]2 (2

Rhodium-Catalyzed Annulation of N-Acetoxyacetanilide with Substituted Alkynes: Conversion of Nitroarenes to Substituted Indoles

A general and efficient rhodium-catalyzed redox-neutral annulation of N-acetoxyacetanilides, readily accessible from nitroarenes, with alkynes has been accomplished for the synthesis of substituted indole derivatives. A wide range of substituted 2,3-diarylindoles were achieved from various substituted N-acetoxyacetanilides and symmetrical/unsymmetrical alkynes in good to excellent yields. The developed method was successfully integrated with the synthesis of N-acetoxyacetanilides for the efficient one-pot synthesis of indoles from nitroarenes. The important features are the introduction of N-acetoxyacetamide as a new directing group, redox-neutral annulation, an additive-free approach, wide functional group tolerance, an intramolecular version, and a one-pot reaction of nitroarenes. The method was further extended to the synthesis of potent higher analogues of indole, viz., pyrrolo[3,2-f]indoles and dibenzo[a,c]carbazoles. In addition, a plausible mechanism was proposed based on the isolation and stoichiometric study of a potential aryl-Rh intermediate.

Mild and efficient synthesis of indoles and isoquinolones via a nickel-catalyzed Larock-type heteroannulation reaction

A simple and efficient approach for the preparation of substituted indoles and isoquinolones via a nickel-catalyzed Larock-type heteroannulation reaction is reported. This transformation employed air-stable and inexpensive Ni(dppp)Cl2 as a precatalyst and Et3N as a mild base. Moreover, the reaction occurs efficiently under mild conditions, and a wide range of substituted indoles and isoquinolones bearing various functional groups are obtained in moderate to excellent yields.

Synthesis of Functionalized (η5-Indenyl)rhodium(III) Complexes and Their Application to C?H Bond Functionalization

It has been established that reductive complexation of functionalized benzofulvenes, which are readily prepared from commercially available indene and 2-methylindene, with RhCl3 in ethanol affords the corresponding indenyl–rhodium(III) dichlorides bearing substituents at the 1- (H or CO2Et), 2- (H or Me), and 3- [CH2Ph or CH2(2-MeOC6H4)] positions. The indenyl–rhodium(III) complexes bearing one ethoxycarbonyl group showed higher thermal stability and regioselectivity than our previously reported CpERhIII complex toward the oxidative [3+2] annulation of acetanilides with internal alkynes.

Indenyl Rhodium Complexes with Arene Ligands: Synthesis and Application for Reductive Amination

An efficient protocol for synthesis of indenyl rhodium complexes with arene ligands has been developed. The hexafluoroantimonate salts [(σ5-indenyl)Rh(arene)](SbF6)2 (arene = benzene (2a), o-xylene (2b), mesitylene (2c), d

Mechanochemical indole synthesis by rhodium-catalysed oxidative coupling of acetanilides and alkynes under solventless conditions in a ball mill

A mechanochemical indole synthesis by rhodium(iii)-catalysed C-H bond functionalisation in a planetary mill has been developed. It occurs in the absence of any solvent, does not require additional heating and only needs catalytic quantities of Cu(OAc)2 in combination with dioxygen as a terminal oxidant. Accordingly, the process represents a powerful and environmentally benign alternative to the common solution-based standard protocols.

Palladium-catalyzed annulation of internal alkynes in aqueous medium

To facilitate precatalyst recovery and reuse, we have developed a fluorous, oxime-based palladacycle 1 and demonstrated that it is a very efficient and versatile precatalyst for carbo- and heteroannulation of internal alkynes with functionalized aryl halides in aqueous medium. A uniform reaction condition for these annulation reactions was also developed.

Oxidative annulation of anilides with internal alkynes using an (Electron-Deficient η5-cyclopentadienyl)rhodium(III) catalyst under ambient conditions

A dinuclear (electron-deficient η5-cyclopentadienyl) rhodium(III) complex was synthesized on a preparative scale via the rhodium-catalyzed cross [2+2+1] cyclotrimerization of silylacetylenes and two alkynyl esters, leading to substituted silylf

Combining Zn ion catalysis with homogeneous gold catalysis: An efficient annulation approach to N-protected indoles

The Fischer indole synthesis is perhaps the most powerful method for indole preparation, but it often suffers from low regioselectivities with unsymmetrical aliphatic ketone substrates and strongly acidic conditions and is not suitable for α,β-unsaturated ketones. In this edge article, we disclose an efficient synthesis of N-protected indoles from N-arylhydroxamic acids/N-aryl-N-hydroxycarbamates and a variety of alkynes via cooperative gold and zinc catalysis. The zinc catalysis is similar to the related zinc ion catalysis in metalloenzymes such as human carbonic anhydrase II and substantially enhances the O-nucleophilicity of N-acylated hydroxylamine by forming the corresponding Zn chelates. The Zn chelates can attack gold-activated alkynes to form O-alkenyl-N-arylhydroxamates, which can undergo facile 3,3-sigmatropic rearrangements and subsequent cyclodehydrations to yield N-protected indole products. This new chemistry offers several important improvements over the Fischer indole synthesis: (a) the reaction conditions are mildly acidic and can tolerate sensitive groups such as Boc; (b) broader substrate scopes including substrates with pendant carbonyl groups (reactive in the Fischer chemistry) and alkyl chlorides; (c) better regioselectivities for the formation of 2-substituted indoles under much milder conditions; (d) 2-alkenylindoles can be prepared readily in good to excellent yields, for which Fischer chemistry could not be used; (e) with internal alkynes both steric and electronic controls are available for achieving good regioselectivities, while Fischer chemistry is in general problematic. The Royal Society of Chemistry 2013.