Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 79, Issue 3, Pages 1047-1054Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo402511b
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Funding
- National Basic Research Program of China [2010CB833300]
- National Natural Science Foundation of China [21025209, 21121062, 21332009, 21302209]
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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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