Synthesis of β-Carbonyl Sulfone Compounds by the Free Radical Coupling Reaction of Sulfonyl Hydrazide and Enol Silyl Ether under Electrochemical Conditions

Abstract

β-羰基砜是一类重要的有机合成砌块，合成该类化合物一直是研究热点。本文以四丁基碘化铵为媒介，在电化学条件下实现烯醇硅醚与各种取代的磺酰肼发生自由基磺酰化反应，经自由基加成和氧化，在最优条件下以55%~76%的收率合成了8种具有不同取代基的β-羰基砜类化合物。采用核磁共振和质谱等手段对产物结构进行表征，并提出了可能的反应机理。 β-carbonyl sulfone is a kind of important organic synthesis block, and the synthesis of this kind of compounds has been a research hotspot. In this paper, β-carbonyl sulfones with different substi-tuents were synthesized by the free radical sulfonation of enol silyl ethers with various substituted sulfonyl hydrazides in the medium of tetrabutylammonium iodide under electrochemical conditions. Through radical addition and oxidation, eight β-carbonyl sulfones with different subs-tituents were synthesized in 55%~76% yield under the optimal conditions. The products were characterized by NMR and MS, and the possible reaction mechanism was proposed.