Hypervalent Iodine-Mediated Chemoselective Bromination of Terminal Alkynes.

ABSTRACT: Practical approaches for chemoselective mono-bromination, di-bromination, and tetra-bromination of terminal alkynes to generate 1-bromoalkynes, 1,2-dibromoalkenes, α,α-dibromoketones, and 1,1,2,2-tetrabromoalkanes based on efficient oxidative brominations mediated by a hypervalent iodine reagent have been developed. Chemoselective bromination can be realized under mild conditions by altering the bromine source. The tetrabutylammonium bromide (TBAB)/(diacetoxyiodo)benzene (PIDA) system is specific for mono-bromination to provide 1-bromoalkynes, while the NaBr/PIDA system is selective toward di-bromination to achieve 1,2-dibromoalkenes. When a certain amount of water was added to the NaBr/PIDA system, a different di-bromination product, α,α-dibromo ketones, was generated. Tetra-bromination o

SUBMITTER: Li Y 

PROVIDER: S-EPMC9021491 | biostudies-literature | 2022

REPOSITORIES: biostudies-literature