Nitric Acid Promoted Metal-Free Bromothiolation of Internal Alkynes with Hydrobromic Acid and Disulfides

Abstract

A novel, metal-free bromo-thiolation of internal alkynes with hydrobromic acid and disulfides has been developed. The reaction is promoted by commercial-grade nitric acid and is used to construct a series of unexplored β-bromoalkenyl sulfides in moderate to good yield. Most products were obtained with high stereoselectivity as syn-configured tetrasubstituted alkenes. Both sulfide groups of the disulfide reagent were used in this method.

Key words

bromo-thiolation - internal alkynes - hydrobromic acid - disulfides - nitric acid - β-bromoalkenyl sulfides - syn-configuration

Publikationsverlauf

Eingereicht: 06. März 2022

Angenommen nach Revision: 01. Juni 2022

Artikel online veröffentlicht:
20. Juli 2022

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