Catalytic C6 Functionalization of 2,3-Disubstituted Indoles by Scandium Triflate
The Journal of Organic Chemistry2014Vol. 79(3), pp. 1047–1054
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Abstract
We report herein an unprecedented direct catalytic C6 functionalization reaction of 2,3-disubstituted indoles with various N-Ts aziridines catalyzed by Sc(OTf)3 under mild conditions. Mechanistic studies revealed that a kinetically favored but reversible formal [3 + 2] annulation occurs initially. The direct C6 functionalization, although having a relatively higher energetic barrier, delivers the thermodynamically favorable products.
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