Alkyne-Based, Highly Stereo- and Regioselective Synthesis of Stereodefined Functionalized Vinyl Tellurides
Citations Over TimeTop 10% of 2000 papers
Abstract
(Z)-beta-Aryltellurovinylphosphonates and (Z)-beta-aryltellurovinyl sulfones were synthesized via the highly stereoselective anti-hydrotelluration of 1-alkynylphosphonates and 1-alkynyl sulfones. The configurations of these compounds were characterized via 1H NMR spectra or NOESY experiments and by X-ray diffraction analysis; (E)-beta-aryltellurovinyl sulfones were obtained with the reaction of sodium aryltellurate with (E)-2-iodovinyl sulfones to confirm the stereochemistry of the above anti-hydrotelluration. When the tandem reaction of alkynes with diaryl ditellurides and sodium arylsulfinates was carried out in AcOH/H2O (4/1), the corresponding (E)-beta-aryltellurovinyl sulfones were obtained in one step in good yields. This reaction is highly regio- and stereoselective and proceeds by using arylsulfinate as the sulfonyl radical precursor and diaryl ditellurides as free radical acceptors. (E)-1-Iodo-2-aryltelluroalkenes can be obtained by the anti-addition of ArTeI with terminal alkynes in THF. The stereochemistry of compound 17b was also determined by X-ray diffraction analysis.
Related Papers
- → Hydrotris(3-mesitylpyrazolyl)borato-copper(i) alkyne complexes: synthesis, structural characterization and rationalization of their activities as alkyne cyclopropenation catalysts(2012)25 cited
- → Strong coordination of cycloheptynes by gold(i) chloride: synthesis and structure of two complexes of the type [(alkyne)AuCl](1998)58 cited
- → Patents and applications of N-sulfonated N-heterocycles(2022)5 cited
- → Syntheses of Diaryl Sulfone. IV(1958)2 cited
- Synthesis of new sulfone containing aza oxa crowns(2012)