Green Access to α-Haloalkyl and α-Halobenzyl Esters, Versatile Intermediates for the One-Pot Two-Step Synthesis of O,O′-Diacyl Acetals Using Zinc-Based Ionic Liquid Catalyst

Fache, Fabienne; Azpiazu, Ignasi de; Pelotier, Béatrice; Piva, Olivier; Gozzi, Christel

doi:10.1055/s-0037-1612415

Cited by 3 publications

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References 10 publications

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“…In 2019, the Fache group reported the access to halobenzyl esters from multicomponent reaction of benzaldehyde, benzoyl chloride and cinnamic acid, by using the zinc‐based ionic liquid as catalyst in one‐pot process. Besides, BMIZnCl 3 was recyclable.…”

Section: Acids As Nucleophiliesmentioning

confidence: 99%

Recent Advances of Cinnamic Acids in Organic Synthesis

et al. 2020

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The great success of cinnamic acids was rooted in their multiple functional groups. Herein, reactions triggered by the radical addition, electrophilic addition, Michael addition and reactions of acids were thoroughly discussed and summarized. Multi-component reactions, rearrange-ments, stereoselective synthesis, coupling, additions will be depicted in detail. This review focused on advances of cinnamic acids in the last decade (2010)(2011)(2012)(2013)(2014)(2015)(2016)(2017)(2018)(2019)(2020). We hope this review will be good for a better understanding of these reagents and future research. * , [7,8] acyl [9] and ketonic [10] radicals were reported. Toluene, [8a-c,9] boron reagents, [8d] aldehydes, [8e] acids, [9b,c] amides, [9d,12e-f] ketones, [10a-b] ethers, [11a-c] alcohols, [12a] epoxides, [12b] nitriles [12a] were able to function as radical precursors.Mao and co-workers [4] reported the decarboxylative methylation of cinnamic acids. The DTBP was employed not only as the oxidant, but also as the methyl source.C vinyl À CF 3 compounds (like Panomifene, and Cyhalothrin) were useful in medicinal chemistry. [5b] Hence, numerous efforts have been devoted to the preparation of these compounds. In this decade, several applications of air-stable Togni's reagent [5a-c,6a] or NaSO 2 CF 3 [5d-f,6b] for the direct C vinyl À CF 3 construction from cinnamic acids have been reported. These radical addition and decarboxylative methods usually required a metal-catalyst (Ir, [5a] Cu [5c,e,6b] ) (Scheme 3)Hu and co-workers [6a] presented a protocol for the construction of C sp2 À CF 2 SO 2 R bonds with a Togni-type reagent. The [a] L.Scheme 1. Classification by mechanism Scheme 2. Radical cascade.

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Section: Acids As Nucleophiliesmentioning

confidence: 99%