201813-48-1

Upstream product

• 13329-40-3 4-Iodoacetophenone 
• 143360-93-4 N-(2-ethynylphenyl)-2,2,2-trifluoroacetamide 
• 42472-69-5 4-ethynylacetophenone 
• 143321-89-5 2,2,2-trifluoro-N-(2-iodophenyl)acetamide 
• 103529-16-4 2-[(trimethylsilyl)ethynyl]aniline 
• 615-43-0 2-iodophenylamine 
• 52670-38-9 2-ethynylaniline 
• 407-25-0 trifluoroacetic anhydride 
• 221910-17-4 1-(4-((2-aminophenyl)ethynyl)phenyl)ethan-1-one 

Downstream Products

• 1286169-98-9 C₂₁H₁₆F₃NO₂ 
• 1385660-29-6 N-tert-butyl-2-(4-acetylphenyl)-1H-indole-3-carboxamide 
• 1224449-86-8 2-[2-(4-acetylphenyl)-1H-indol-3-yl]cyclohex-2-en-1-one 

Relevant academic research and scientific papers

3-Aryl-2-unsubstituted indoles through the palladium-catalysed reaction of o-ethynyltrifluoroacetanilide with aryl iodides

The reaction of the readily available o-ethynyltrifluoroacetanilide with aryl iodides in the presence of catalytic amounts of Pd2dba3, an excess of K2CO3, in DMSO at 40°C affords 2-unsubstituted-3-arylindoles in good yield. Subjection of o-ethynyltrifluoroacetanilide to the same reaction conditions in the absence of aryl iodides gives rise to the formation of indole in high yield.

3-(2-Alken-1-one-2-yl)indoles through the palladium-catalyzed reaction of 2-alkynyltrifluoroacetanilides with cyclic α-iodoenones

α-Iodoenones can be efficiently employed as organic electrophiles in the Pd-catalyzed synthesis of 2,3-disubstituted indoles from 2-alkynyltrifluoroacetanilides. Best results were obtained using the weak ligand As(Ph)3. The methodology reported provides an efficient entry to indoles bearing a 2-alkenon-2-yl moiety linked in the 3-position, that possesses a scarcely reported substitution pattern.

2-Aryl and 2-Heteroaryl Indoles from 1-Alkynes and o- lodotrifluoroacetanilide through a Domino Copper-Catalyzed Coupling-Cyclization Process

(Matrix presented) A general method for the synthesis of 2-aryl and 2-heteroaryl indoles from aryl iodides and 1-alkynes through a domino copper-catalyzed process is reported. The best results have been obtained with [Cu(phen)(PPh3)2]NO3 in the presence of K 3PO4 in toluene or dioxane at 110°C. 2-Aryl and 2-heteroaryl indoles can also be isolated in good yields by using catalysts derived from Cul and PPh3 in dioxane at 110°C.

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.