1094425-38-3Relevant academic research and scientific papers
A novel synthetic route to 3-sulfenyland 3-selenylindoles by n-bu 4ni-induced electrophilic cyclization
Chen, Yu,Cho, Chul-Hee,Larock, Richard C.
, p. 173 - 176 (2009)
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.
Dual selectivity: Electrophile and nucleophile selective cross-coupling reactions on a single aromatic substrate
Heinrich, Annika C. J.,Thiedemann, Birk,Gates, Paul J.,Staubitz, Anne
supporting information, p. 4666 - 4669 (2013/10/08)
The development of a high yielding, both nucleophile and electrophile selective cross-coupling reaction with aromatic rings is presented. The reaction is general with respect to functional groups. Furthermore, the products still contain a boronic ester and a bromide. These two functional groups allow them to be easy-to-prepare, highly complex starting materials for further reactions, avoiding protecting group transformations.
An efficient, microwave-assisted, one-pot synthesis of indoles under Sonogashira conditions
Chen, Yu,Markina, Nataliya A.,Larock, Richard C.
experimental part, p. 8908 - 8915 (2009/12/08)
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.
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
Chen, Yu,Cho, Chul-Hee,Shi, Feng,Larock, Richard C.
supporting information; experimental part, p. 6802 - 6811 (2009/12/30)
(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.
