Synthesis and reactivity of α-sulfenyl-β-chloroenones, including oxidation and Stille cross-coupling to form chalcone derivatives

TETRAHEDRON

卷:88

Article

Kearney, Aoife M.¹  Murphy, Linda¹  Murphy, Chloe C.¹  Eccles, Kevin S.¹  Lawrence, Simon E.²  Collins, Stuart G.²  Maguire, Anita R.^2,3 

[1] Univ Coll Cork, Sch Chem, Analyt & Biol Chem Res Facil, Cork, Ireland

[2] Univ Coll Cork, Synth & Solid State Pharmaceut Ctr, Sch Chem, Analyt & Biol Chem Res Facil, Cork, Ireland

[3] Univ Coll Cork, Sch Chem, Cork, Ireland

关键词: Chalcones;    Chlorination;    Oxidation;    Stille cross-coupling;    alpha-Sulfenyl-beta-chloroenones;   

DOI  :  10.1016/j.tet.2021.132091

来源: Elsevier

【 摘 要 】

The synthesis of a range of novel alpha-sulfenyl-beta-chloroenones from the corresponding a-sulfenylketones, via a NCS mediated chlorination cascade, is described. The scope of the reaction has been investigated and compounds bearing alkyl- and arylthio substituents have been synthesised. In most instances, the Z alpha-sulfenyl-beta-chloroenones were formed as the major products, while variation of the substituent at the beta-carbon position led to an alteration in stereoselectivity. Stille cross-coupling with the Z alpha-sulfenyl-beta-chloroenones led to selective formation of Z sulfenyl chalcones, while the E alpha-sulfenyl-beta-chloroenones did not react under the same conditions. Oxidation of the Z alpha-sulfenyl-beta-chloroenones was followed by isomerisation, leading to the E alpha-sulfinyl-beta-chloroenones. Stille cross-coupling with the E alpha-sulfinyl-beta-chloroenones produced the E sulfinyl chalcones. Either the E or Z sulfinyl chalcones can be obtained by altering the sequence of oxidation and Stille cross-coupling. (C) 2021 The Author(s). Published by Elsevier Ltd.

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