Regioselective Pd-catalyzed α-alkylation of furans using alkyl iodides

Yuan, Jiaqi; Zhang, Xiaofei; Yang, Chunhao

doi:10.1039/d1ra01522b

Cited by 7 publications

(1 citation statement)

References 29 publications

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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%

C−H Activation Based Functionalization of Furfural Derivatives

et al. 2022

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Dedicated to Professor Cesare Gennari on the occasion of his 70th birthday.Furfural and related compounds are building blocks of industrial interest, obtained from raw biomass. Their use as precursors of basic and fine chemicals has gained increasing attention as a green alternative to petroleum-derived compounds. Several works have reported the functionalization of furfurals to obtain a wider range of chemicals, opening up new synthetic possibilities and applications, ranging from biofuels to pharmaceuticals. Among these works, processes based on CÀ H activation are the most attractive ones for their atom economy and the possibility to use non-activated substrates. This minireview summarizes the reported methods of direct CÀ H functionalization of furfurals without prior modification of the redox state of the aldehyde function. In particular, the transition metal catalyzed functionalization of each bond of the heteroaromatic nucleus of these molecules is systematically discussed, as well as examples of CÀ H transformations of the aldehyde function.

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Section: Alkylationmentioning

confidence: 99%

C−H Activation Based Functionalization of Furfural Derivatives

et al. 2022

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Synthesis of Alkylated Carbonyl‐Bearing Furans via Acid‐Catalyzed Friedel‐Crafts Reaction

Tkachenko,

Ivanova,

Khrapovitskaya

et al. 2024

Asian J Org Chem

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Carbonyl‐bearing furans, certain pyrroles, and thiophenes were alkylated using alcohols in an acidic medium. Some 5‐alkylated derivatives of 2‐furoic acid with various adamantyls‐, cycloalkyl‐, other 2°‐ and 3°‐alkyl substituents were synthesized using 2‐furoic acid as a biomass‐derived chemical platform. Side reaction resulted in the substitution of the carboxylic group, leading to the formation of 1,5‐dialkyl furans. In the alkylation of acyl and formyl furan, either mono‐ or di‐alkyl products were obtained, depending on the functional group present in the furan nucleus. Pyrroles (or thiophenes) with related functional groups exclusively (or near‐exclusively) yielded mono‐alkyl products. The resultant 5‐substituted carbonyl furans can be used as building blocks and synthetic equivalents for 1C and 4C synthons, as demonstrated by a series of reactions involving 5‐adamantan‐1‐yl‐2‐furoic acid.

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