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Catalyst-Free α--Selective Hydroboration and ()-Selective Deuterated Semihydrogenation of Alkynyl Sulfones. | LitMetric

Catalyst-Free α--Selective Hydroboration and ()-Selective Deuterated Semihydrogenation of Alkynyl Sulfones.

J Org Chem

Key Laboratory of Biocatalysis & Chiral Drug Synthesis of Guizhou Province, Generic Drug Research Center of Guizhou Province, School of Pharmacy, Zunyi Medical University, Zunyi 563000, China.

Published: June 2024

AI Article Synopsis

Article Abstract

Here, we present a straightforward α--selective hydroboration of alkynyl sulfones with NHC-boranes without the need for a catalyst. This reaction is compatible with a wide range of substrates for efficiently producing structurally diverse α-borylated vinyl sulfones in satisfactory yields. The hydride transfer from NHC-borane to alkynyl triflone is studied by density functional theory (DFT) calculations for -hydroboration. Moreover, a regiodivergent deuterated semihydrogenation of alkynyl triflones has also been developed using DO as the deuterium source. A variety of diversity-oriented D-containing vinyl triflones were prepared in good to excellent yields with excellent deuterium incorporation ratios. Synthetic manipulations of the deuterated products are achieved for the conversion into valuable deuterated molecules, indicating the utility of this protocol.

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Source
http://dx.doi.org/10.1021/acs.joc.3c02833DOI Listing

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