Journal
SYNTHESIS-STUTTGART
Volume 53, Issue 20, Pages 3744-3750Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/a-1493-6885
Keywords
N-selenocyanato-dibenzenesulfonimide; electrophilic seleno-cyanation; chromane; dihydrobenzofuran; organoselenium compound
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Funding
- NSFC [21871178, 22071149, 21702135]
- STCSM [19JC1430100]
- Program for Professor of Special Appointment (Eastern Scholar) at Shanghai Institutions of Higher Learning
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A new electrophilic selenocyanation reagent was prepared from commercially available dibenzenesulfonimide for the first time, leading to various SeCN-containing compounds. The reagent was utilized in electrophilic selenocyanato reactions of nucleophiles as well as in a tandem selenocyanation/cyclization reaction of alkenes with phenols, providing simple methods for the formation of different SeCN-containing products.
A new electrophilic selenocyanation reagent N-seleno-cyanato-dibenzenesulfonimide was readily prepared in two steps from commercially available dibenzenesulfonimide for the first time. A variety of electrophilic selenocyanato reactions of nucleophiles have been achieved using it as selenocyanato source under mild and simple conditions. Numerous SeCN-containing compounds were obtained in moderate to excellent yields. Meanwhile, a Lewis acid mediated tandem selenocyanation/cyclization reaction of alkenes with phenols, which provided simple methods for the formation of various SeCN-containing chromanes and dihydrobenzofurans in moderate to good yields, has also been developed.
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