Organic letters

Synthesis of indole and biindolyl triflones: Trifluoromethanesulfonylation of indoles with Tf2O/TTBP (2, 4, 6-tri-tert-butylpyridine) system

XH Xu, GK Liu, A Azuma, E Tokunaga, N Shibata

Index: Xu, Xiu-Hua; Liu, Guo-Kai; Azuma, Ayaka; Tokunaga, Etsuko; Shibata, Norio Organic Letters, 2011 , vol. 13, # 18 p. 4854 - 4857

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Citation Number: 34

Abstract

A convenient synthesis of indole triflones is reported. N-Alkyl, aryl and NH indole triflones were obtained in 82–96% yields by the Tf2O/TTBP System. Biindolyl triflones were accessed in 51–81% yields for the first time by simple treatment of the resulting indole triflones with a base and without any use of organometallic chemistry. An environmentally friendly solvent, Solkane 365/227, can be substituted for this process without any loss of efficiency.