Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 81, Issue 8, Pages 3246-3255Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.6b00203
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Funding
- National Natural Science Foundation of China [21273068, 21373003, J1210040]
- Fundamental Research Funds for the Central University, Hunan University
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We describe here an efficient route for the synthesis of (Z)-vinylic sulfides 3 via the highly regio- and stereoselective coupling of (Z)-1,2-bis(aryl(alkyl)thio)alkenes and Grignard reagents over a Ni catalyst under mild conditions. (Z)-Vinylic sulfides 3 are important intermediates in the synthesis of tri- and tetrasubstituted alkenes that are important construction blocks for drugs and natural products. The directing organosulfur groups (SR) can be converted to diaryl(alkyl) disulfides (RSSR) using H2O2 as oxidant, hence avoiding the waste of sulfur resources. The protocol provides a general method that is highly regio- and stereoselective for the synthesis of a diversity of tri- and tetrasubstituted alkenes.
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