- Iron-facilitated iodine-mediated electrophilic annulation of N,N-dimethyl-2-alkynylanilines with disulfides or diselenides
-
An efficient synthesis of N-methyl-3-chalcogeno-indoles has been developed via iodine-mediated electrophilic annulation reactions of 2-alkynylaniline derivatives with disulfides or diselenides. In the presence of iodine and iron, a variety of 2-alkynylani
- Du, Hui-Ai,Tang, Ri-Yuan,Deng, Chen-Liang,Liu, Yan,Li, Jin-Heng,Zhang, Xing-Guo
-
experimental part
p. 2739 - 2748
(2011/12/01)
-
- 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.
- Chen, Yu,Cho, Chul-Hee,Shi, Feng,Larock, Richard C.
-
supporting information; experimental part
p. 6802 - 6811
(2009/12/30)
-
- 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.
- Chen, Yu,Cho, Chul-Hee,Larock, Richard C.
-
scheme or table
p. 173 - 176
(2009/06/20)
-