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Indolenines were generated at −78°C from 3-benzylic or 3-allylic indoles by dehydrogenation with N-tert-butylbenzenesulfinimidoyl chloride, and a carbon–carbon bond was formed at −78°C in a one-pot manner by treating these indolenines with various carbon nucleophiles such as active methylene compounds or organocuprates.
One-pot substitution of a C–H bond at the position next to the nitrogen atom of lactams with alkyl malonates proceeded effectively by dehydrogenation of lactams with N-tert-butylbenzenesulfinimidoyl chloride, followed by Mannich-type addition of alkyl malonates.
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