Abstract
Azidation of indoles using iodine and copper bromide as catalysts under ambient reaction conditions is presented. The regioselectivity is directed by the substituent at the C3-position of indole. A radical stabilizing group such as an ester or ketone moiety at the C3-position of indole leads to azidation at the C2-position, whereas a less radical stabilizing group such as an alkyl or amide group at the C3-position of indole furnishes the 3-azidooxindole product. This protocol is mild and efficient to obtain several 2-azidoindole derivatives and 3-azidooxindole derivatives in moderate to good yields. The reaction conditions hold well for gram-scale synthesis.
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