Mechanosynthesis of phosphonocinnamic esters through solvent-free Horner-Wadsworth-Emmons reaction

Jiménez-Arellanes, María Adelina; Peña‐Rico, M. A.; Castro-Cerritos, Karla Viridiana; Sifuentes-Vázquez, Luis Daniel; Reyes-González, Miguel Ángel; Ramírez-Marroquín, Oscar Abelardo

doi:10.1080/10426507.2022.2053976

Cited by 2 publications

(4 citation statements)

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“…[47][48][49][50] Despite its potential, solvent-free or LAG Wittig-type reactions are relatively underexplored in the literature (Figure 1). Most reports focus on stabilized phosphonium ylides in the Horner-Wadsworth-Emmons (HWE) modification of the Wittig reaction [51][52][53][54][55][56] or semi-stabilized ylides from benzyl phosphonium salts. [57][58][59][60] While these reactions are conducted under neat conditions, some protocols still require external heating, such as conventional heating via an oil bath or microwave irradiation, to provide the necessary energy.…”

Section: Introductionmentioning

confidence: 99%

“…51,53 Reports relying solely on mechanical force to drive the reaction are scarce. 52,54,[57][58][59]61 In 2018, Mack explored the diastereoselectivity of the Wittig reaction on benzaldehyde under LAG using benzyltriphenylphosphonium bromide. 57 And very recently Friščić reported a hexameric supramolecular cage assembly constructed from (dibromomethyl)triphenylphosphonium bromide units.…”

Section: Introductionmentioning

confidence: 99%

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High-speed Ball Milling Enables an Ultra-fast Wittig Olefination Under Ambient and Solvent-free Conditions Without Ylide Pre-formation

Templ,

Schnürch

2024

Preprint

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30 Seconds to success! – The Wittig reaction, a fundamental and extensively utilized reaction in organic chemistry, enables the efficient conversion of carbonyl compounds to olefins using phosphonium salts. Traditionally, meticulous reaction setup, including the pre-formation of a reactive ylide species via deprotonation of a phosphonium salt, is crucial for achieving high-yielding reactions under classical solution-based conditions. In this report, we present an unprecedented protocol for an ultra-fast mechanochemically driven Wittig reaction under solvent-free and ambient conditions, eliminating the need for tedious ylide pre-formation under strict air and moisture exclusion. A range of aldehydes and ketones were reacted with diverse phosphonium salts under high-speed ball milling conditions, giving access to the respective olefins in only 30 seconds.

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