90901-80-7

Upstream product

• 90901-75-0 o-(1-benzoyl-3-butenyl)phenyl isocyanide 
• 591-80-0 pent-4-enoic acid 
• 59-88-1 phenylhydrazine hydrochloride 
• 591-51-5 phenyllithium 
• 948-65-2 2-phenyl-indole 
• 107-18-6 allyl alcohol 
• 591-50-4 iodobenzene 
• 1006727-95-2 allyl(2-ethynylphenyl)amine 
• 69622-49-7 2-(2-isocyanophenyl)-1-phenylethanone 
• 536-74-3 phenylacetylene 
• 143360-89-8 o-(phenylethynyl)trifluoroacetanilide 
• 13141-38-3 2-phenylethynylaniline 
• 615-43-0 2-iodophenylamine 
• 201813-54-9 N-Allyl-2,2,2-trifluoro-N-(2-phenylethynyl-phenyl)-acetamide 

Relevant academic research and scientific papers

Sequential Sonogashira/intramolecular aminopalladation/cross-coupling ofortho-ethynyl-anilines catalyzed by a single palladium source: rapid access to 2,3-diarylindoles

We have developed a practical and efficient one-pot protocol for the synthesis of 2,3-diarylindolesviaPd-catalyzed bis-arylative cyclization of variouso-ethynylanilines with aryl iodides. Mechanism studies showed that a Pd-catalyzed Sonogashira reaction took place firstly, giving an internal alkyne intermediate, which subsequently underwent intramolecular aminopalladation/cross-coupling to give access to 2,3-diarylindoles. The present methodology exhibits a broad substrate scope, producing various 2,3-diaryl indoles bearing two different aryl groups.

Access to 3-Oxindoles from Allylic Alcohols and Indoles

The site-selective and regioselective allylation of 2-substituted indoles was performed by using a ruthenium(IV) precatalyst containing a phosphine–sulfonate chelate. Mono-, di-, and triallylated indoles were selectively obtained depending on the reaction

Fast, efficient Ru(IV)-catalysed regioselective allylation of indoles using allyl alcohol (without additives) under mild conditions

The new Ru(iv) salt, [Ru(η3-C3H 5)(Cp*)(CH3CN)2](PF6) 2, is an excellent catalyst for the regioselective allylation of a variety of indole compounds using allyl alcohol as substrate; there are no co-catalysts required in this chemistry and the yields and reaction conditions are very favorable. The Royal Society of Chemistry.

Multiple component Fischer indole reactions

New 3-component variations of the Fischer synthesis of substituted indoles have been developed based on the reaction of organometallic reagents with nitriles or carboxylic acids. The new variations expand the scope and synthetic utility of the method.

Palladium-Catalyzed Cyclization of o-Alkynyltrifluoroacetanilides with Allyl Esters. A Regioselective Synthesis of 3-Allylindoles

The reaction of readily available o-alkynyltrifluoroacetanilides 1 with allyl esters provides a valuable new route to 3-allylindoles 3. Three basic procedures have been developed: a stepwise method based on the isolation of the N-allyl derivative 4 and its subsequent cyclization to 3 (procedure a), a one-pot reaction omitting the isolation of 4 (procedure b), and a procedure which most probably leads to the formation of 3 through a mechanism not involving the intermediacy of 4 (procedure c). In the presence of the electron-rich sterically encumbered ligand tris(2,4,6-trimethoxyphenyl)-phosphine (ttmpp) the reaction exhibits remarkable regioselectivity and almost exclusive formation of 3-allylindoles with the indolyl moiety bound to the less substituted allyl terminus is usually observed. However, some loss of olefin geometry is observed.

INDOLE SYNTHESES UTILIZING o-METHYLPHENYL ISOCYANIDES.

New indole synthesis starting with o-methylphenyl isocyanides such as o-tolyl, 2,4-xylyl, and 2,6-xylyl isocyanide is described. Treatment of o-tolyl isocyanide with LDA in diglyme at minus 78 degree C generated selectively o-(lithiomethyl)phenyl isocyanide in an almost quantitative yield, which on warming up to room temperature was cyclized to indole after aqueous workup. Similarly, 2,4-xylyl and 2,6-xylyl and 2,6-xylyl isocyanides were cyclized to 5-methylindole and 7-methylindole quantitatively. The o-(lithiomethyl)phenyl isocyanides reacted with electrophiles such as alkyl halides and alkylene oxides to give o-alkylphenyl isocyanides, which were cyclized via the lithiation at the orthobenzylic carbon to afford 3-substituted indoles.