Double C–N bond cleavages of N-alkyl 4-oxopiperidinium salts: access to unsymmetrical tertiary sulfonamides

Abstract

In this paper, regiospecific, double intraannular C–N bond cleavages of N-alkyl 4-oxopiperidinium salts are presented.

Photocatalyzed Dehydroxylative Amination of Phenols: A Ring-Expansion Approach for Medium-Sized Benzolactams

“…Synthetically, the C–N bond cleavage and transformation of cyclic tertiary aliphatic amines is a valuable research topic in that C–N bond dissociation and ring opening would provide a carbon and a nitrogen terminal, making a diversified scaffold for future transformation . In this scenario, we recently showed that the formation of a charge-transfer complex could greatly attenuate the C–N bond in tertiary alkylamines . In view of the fact that phenols are readily available aromatic species that participate in many oxidative coupling reactions, we hypothesized that phenols might be capable of coupling to cyclic tertiary alkylamines via the radical C–N bond cleavage pathway.…”

Photocatalyst-, metal- and additive-free regioselective radical cascade sulfonylation/cyclization of benzimidazole derivatives with sulfonyl chlorides induced by visible light

“…With the prevailing eco-friendly concept, chemists are dedicated to green and efficient strategies for the generation of the sulfonyl radical, especially under photoredox catalysis. It is well known that there are a lot of easily available sulfonyl sources, such as sulfonyl chlorides, 7 sodium sulfinate, 8 sulfinic acid, 9 and sulfonyl hydrazide, 10 which can be transformed into sulfonyl radicals under photocatalytic conditions. 11 Despite the significance of these developments, the successful application of the above-mentioned protocols often requires external photocatalysts, transition metals, or additives to facilitate the single electron transfer (SET) process.…”