1094425-18-9

Upstream product

• 1094425-38-3 N,N-dimethyl-4-bromo-2-iodoaniline 
• 536-74-3 phenylacetylene 

Downstream Products

• 1094425-10-1 5-bromo-1-methyl-3-(4-nitrophenylsulfenyl)-2-phenylindole 
• 1196786-01-2 5-bromo-1-methyl-2-phenyl-3-(thiophen-2-yl)indole 
• 1185743-94-5 5-bromo-1-methyl-2-phenyl-3-(phenylsulfenyl)indole 
• 1386875-63-3 (5-bromo-1-methyl-1H-indol-3-yl)(phenyl)methanone 
• 1401560-41-5 8-bromo-11-methyl-5,6-diphenyl-11H-benzo[a]carbazole 

Relevant academic research and scientific papers

Palladium(II)-catalyzed tandem cyclization/C-H functionalization of alkynes for the synthesis of functionalized indoles

A palladium-catalyzed tandem cyclization/C-H functionalization of two alkynes was accomplished to construct a series of polycyclic functionalized indoles. A range of internal alkynes bearing synthetically useful functional groups were tolerated. A good regioselectivity was observed when alkyl-substituted alkynes were introduced into the reaction system, and a single product was obtained. Molecular oxygen was used as the terminal oxidant in the approach, rendering the reaction more sustainable.

A novel synthetic route to 3-sulfenyland 3-selenylindoles by n-bu 4ni-induced electrophilic cyclization

3-Sulfenyl-and 3-selenylindoles are prepared in excellent yields by the palladium/copper-catalyzed crossing coupling of N,N-dialkyl-o-iodoanilines and terminal alkynes, followed by electrophilic cyclization with arylsulfenyl chlorides and arylselenyl chlorides in the presence of a stoichiometric amount of n-Bu4NI.

Synthesis of 3-sulfenyl- and 3-selenylindoles by the Pd/Cu-catalyzed coupling of N,N-dialkyl-2-iodoanilines and terminal alkynes, followed by n-Bu4NI-induced electrophilic cyclization

(Chemical Equation Presented) 3-Sulfenyl- and 3-selenylindoles are readily synthesized by a two-step process involving the palladium/copper-catalyzed crossing coupling of N,N-dialkyl-ortho-iodoanilines and terminal alkynes and subsequent electrophilic cyclization of the resulting N,N-dialkyl-ortho-(1- alkynyl)anilines with arylsulfenyl chlorides or arylselenyl chlorides. The presence of a stoichiometric amount of n-Bu4NI is crucial to the success of the electrophilic cyclization. A variety of 3-sulfenyl- and 3-selenylindole derivatives bearing alkyl, vinylic, aryl, and heteroaryl substituents have been prepared in good to excellent yields (up to 99%). By employing N,N-dibenzyl-ortho-iodoanilines, a 3-sulfenyl-N-H-indole has been successfully prepared. In addition, 3-sulfonyl- and 3-sulfinylindoles have also been successfully prepared by facile oxidation of the corresponding 3-sulfenylindoles.

An efficient, microwave-assisted, one-pot synthesis of indoles under Sonogashira conditions

A microwave-assisted, one-pot, three-component coupling reaction for the synthesis of indoles has been developed. The reaction is carried out in two steps under standard Sonogashira coupling conditions from an N-substituted/N,N-disubstituted 2-iodoaniline and a terminal alkyne, followed by the addition of acetonitrile and an aryl iodide. A variety of polysubstituted indoles have been prepared in moderate to excellent yields using the present method.