N‑Heterocyclic Carbene-Catalyzed Olefination of Aldehydes with Vinyliodonium Salts To Generate α,β-Unsaturated Ketones

An organocatalyzed metal-free, direct olefination of aldehydes with vinyliodonium salts has been achieved by an N-heterocyclic carbene-promoted C–H bond activation. The reaction proceeds under very mild conditions, delivering a range of (hetero)­aryl-vinyl ketones in good yields. The retention of th...

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Veröffentlicht in:Organic letters 2018-04, Vol.20 (7), p.1906-1909
Hauptverfasser: Rajkiewicz, Adam A, Kalek, Marcin
Format: Artikel
Sprache:eng
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Zusammenfassung:An organocatalyzed metal-free, direct olefination of aldehydes with vinyliodonium salts has been achieved by an N-heterocyclic carbene-promoted C–H bond activation. The reaction proceeds under very mild conditions, delivering a range of (hetero)­aryl-vinyl ketones in good yields. The retention of the double bond configuration is uniformly observed, and the application of 2-methoxyphenyl auxiliary group in iodonium salts secures a complete selectivity of the vinyl transfer.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b00447