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Synthesis of heteroarylated ketones via bismuth(III) triflate-promoted regioselective 1,4- and 1,6-additions of electron-rich heteroarenes to cyclic enones and dienones

Author:
Metz, Tanner L., Leng, Mingwan, Evans, Joshua, Stanley, Levi M.
Source:
Tetrahedron 2018 v.74 no.26 pp. 3283-3292
ISSN:
0040-4020
Subject:
Lewis bases, bismuth, chemical reactions, chemical structure, ketones, pyrroles, regioselectivity, thiophene
Abstract:
The development and optimization of bismuth(III) triflate-promoted regioselective 1,4- and 1,6-additions of electron-rich heteroarenes to cyclic, β,β-disubstituted enones and dienones is described. Additions of a range of heteroarenes, including furan, thiophene, pyrrole, and indole nucleophiles, to cyclic, β,β-disubstituted enones occur to form all-carbon quaternary centers in up to 88% yield. In addition, regioselective 1,6-additions of electron-rich heteroarenes to 3-vinyl-2-cyclohexenone occur to produce a variety of δ-heteroarylated, β,β-disubstituted enones in up to 93% yield. The high 1,6-selectivity for these reactions is attributed to the increased steric bulk at the β-position relative to the δ-position, and no competing 1,4-conjugate addition is observed.
Agid:
5971818