The formyl C-H thiolation of aldehydes using thiosulfonates using the decatungstate anion as a photocatalyst is reported. Using this photocatalytic protocol, both aromatic and aliphatic thioesters can be synthesized in good yields. The transformat...
Artikel
Thiophane‐Catalyzed Umpolung of N‐Bromoimides for Dibromination of Olefins
European Journal of Organic Chemistry, März 2024, DOI. Login für Volltextzugriff.
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This work reports a thiophane-catalyzed dibromination of olefins using NBS as the sole bromine source, wherein a new type of catalytic umpolung strategy of N-bromoimides is revealed. The mechanistic investigation revealed that in situ generated 2,3-dihydrothiophene was the actual catalyst, which was responsible for the catalytic umpolung of NBS.
Abstract
A thiophane-catalyzed dibromination of olefins using NBS as the sole bromine source has been developed, providing a low-cost and mild methodology for preparing vicinally dibrominated compounds from electron-neutral or -deficient alkenes. The mechanistic investigation showed that 2,3-dihydrothiophene generated in situ from the reaction of thiophane with NBS was the actual catalyst, which reversed the polarity of NBS to yield bromide ion.
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