Rhodium(III)-catalysed, redox-neutral C(sp2)-H alkenylation using pivalimide as a directing group with internal alkynes

[Display omitted] •Regioselective pivalimide directed alkenylation.•Redox-neutral.•Broad scope (30 examples) and yields of up to 90%. In the presence of [RhCp∗Cl2]2, N-pivaloyl anilines react with internal alkynes to give the corresponding 2-alkenylpivalimides under redox neutral conditions through...

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Veröffentlicht in:Tetrahedron letters 2017, Vol.58 (1), p.1-4
Hauptverfasser: Kathiravan, Subban, Nicholls, Ian A.
Format: Artikel
Sprache:eng
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Zusammenfassung:[Display omitted] •Regioselective pivalimide directed alkenylation.•Redox-neutral.•Broad scope (30 examples) and yields of up to 90%. In the presence of [RhCp∗Cl2]2, N-pivaloyl anilines react with internal alkynes to give the corresponding 2-alkenylpivalimides under redox neutral conditions through C-H activation. This redox neutral hydroarylation, which does not require an external organic acid, unlocks a regioselective synthetic route to 2-alkenyl anilines and is generally applicable to diversely substituted electron rich and electron poor pivalimides.
ISSN:0040-4039
1359-8562
1873-3581
DOI:10.1016/j.tetlet.2016.11.039