Visible Light-Enabled sp³ -C-H Functionalization with Chloro- and Bromoalkynes: Chemoselective Route to Vinylchlorides or Alkynes.

ABSTRACT: An unprecedented direct atom-economic chemo- and regioselective hydroalkylation of chloroalkynes and an sp³ -C-H alkynylation of bromoalkynes was achieved. The reaction partners are unfunctionalized ethers, alcohols, amides, and even non-activated hydrocarbons. We found that a household fluorescent bulb was able to excite a diaryl ketone, which then selectively abstracts a H-atom from an sp³ -C-H bond. The product of a formal alkyne insertion into the sp³ -C-H bond was obtained with chloroalkynes, providing valuable vinyl chlorides. The photo-organocatalytic hydrogen atom transfer strategy gives rise to a broad range of diversely functionalized olefins. When bromoalkynes are applied in the presence of a base, a chemoselectivity switch to an alkynylation is

SUBMITTER: Adak T 

PROVIDER: S-EPMC7756539 | biostudies-literature | 2020 Dec

REPOSITORIES: biostudies-literature