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

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Date
2021-03-26
Authors
Kearney, Aoife M.
Murphy, Linda
Murphy, Chloe
Eccles, Kevin S.
Lawrence, Simon E.
Collins, Stuart G.
Maguire, Anita R.
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Elsevier
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Abstract
The synthesis of a range of novel α-sulfenyl-β-chloroenones from the corresponding α-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 α-sulfenyl-β-chloroenones were formed as the major products, while variation of the substituent at the β-carbon position led to an alteration in stereoselectivity. Stille cross-coupling with the Z α-sulfenyl-β-chloroenones led to selective formation of Z sulfenyl chalcones, while the E α-sulfenyl-β-chloroenones did not react under the same conditions. Oxidation of the Z α-sulfenyl-β-chloroenones was followed by isomerisation, leading to the E α-sulfinyl-β-chloroenones. Stille cross-coupling with the E α-sulfinyl-β-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.
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Keywords
Chalcones , Chlorination , Oxidation , Stille cross-coupling , Thioamides , Transformation , Tools , α-Sulfenyl-β-chloroenones
Citation
Kearney, A., Murphy, L., Murphy, C., Eccles, K., Lawrence, S., Collins, S. and Maguire, A., (2021) 'Synthesis and reactivity of α-sulfenyl-β-chloroenones, including oxidation and Stille cross-coupling to form chalcone derivatives', Tetrahedron, 88, 132091 (12 pp). doi: 10.1016/j.tet.2021.132091