2021
DOI: 10.1039/d1ra01522b
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Regioselective Pd-catalyzed α-alkylation of furans using alkyl iodides

Abstract: A practical and regioselective strategy to synthesize α-alkylfurans via Pd-catalyzed direct C–H alkylation using alkyl iodides was developed.

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Cited by 5 publications
(1 citation statement)
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“…Addition of the radical to the heteroarene, followed by electron rebound to the metal regenerates the starting Pd(0) complex and a carbocation intermediate, which undergoes base promoted elimination to give the alkylated heteroarene. [86] These Pd-catalyzed couplings with unactivated (typically secondary and tertiary) alkyl halides have recently been shown to work under much milder conditions with the assistance of visible light. [87,88] Using FeCl 2 , a radical approach has also been developed by Nishikata to carry out the selective functionalization of furfural derivatives (1 or 29) at the C5 position (Scheme 23).…”
Section: Alkylationmentioning
confidence: 99%
“…Addition of the radical to the heteroarene, followed by electron rebound to the metal regenerates the starting Pd(0) complex and a carbocation intermediate, which undergoes base promoted elimination to give the alkylated heteroarene. [86] These Pd-catalyzed couplings with unactivated (typically secondary and tertiary) alkyl halides have recently been shown to work under much milder conditions with the assistance of visible light. [87,88] Using FeCl 2 , a radical approach has also been developed by Nishikata to carry out the selective functionalization of furfural derivatives (1 or 29) at the C5 position (Scheme 23).…”
Section: Alkylationmentioning
confidence: 99%