1-Chloromethyl-4-fluoro-1,4-diazoniabicyclo[2,2,2]octane bis(tetrafluoroborate) as novel and versatile reagent for the rapid thiocyanation of indoles, azaindole, and carbazole

Yadav, J. S. ; Subba Reddy, B. V. ; Jayasudhan Reddy, Y. (2008) 1-Chloromethyl-4-fluoro-1,4-diazoniabicyclo[2,2,2]octane bis(tetrafluoroborate) as novel and versatile reagent for the rapid thiocyanation of indoles, azaindole, and carbazole Chemistry Letters, 37 (6). p. 652. ISSN 0366-7022

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Official URL: http://www.jstage.jst.go.jp/article/cl/37/6/37_652...

Related URL: http://dx.doi.org/10.1246/cl.2008.652

Abstract

SelectfluorTM is found to catalyze efficiently the electrophilic thiocyanation of indoles and pyrrole with ammonium thiocyanate under mild and neutral conditions to produce the corresponding 3-indolyl and 2-pyrrolyl thiocyanates, respectively, in excellent yields with high selectivity. This method is effective even with azaindole and carbazole while many of reported procedures failed to produce thiocyanates from azaindole.

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