Acetone Cyanohydrin

Haroutounian, Serkos A.

doi:10.1002/047084289x.ra014

Cited by 6 publications

(2 citation statements)

References 19 publications

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“…The choice of the cyanide anion source was an important design issue, because it had to be safe, environmentally friendly and suitable for the generation of cyanide anion under basic conditions, without introducing other reactive species into the catalytic cycle. Among of the commercially available cyanide precursors, we chose acetone cyanohydrin ( 5 ) because it meets all these criteria: it is safe [ 17 ] and it releases cyanide anion and acetone (waste) in the presence of bases [ 18 ]. The presence of acetone in the reaction medium should not introduce reactivity distortion issues in the catalytic process.…”

Section: Resultsmentioning

confidence: 99%

Cyanovinylation of Aldehydes: Organocatalytic Multicomponent Synthesis of Conjugated Cyanomethyl Vinyl Ethers

2021

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A novel organocatalytic multicomponent cyanovinylation of aldehydes was designed for the synthesis of conjugated cyanomethyl vinyl ethers. The reaction was implemented for the synthesis of a 3-substituted 3-(cyanomethoxy)acrylates, using aldehydes as substrates, acetone cyanohydrin as the cyanide anion source, and methyl propiolate as the source of the vinyl component. The multicomponent reaction is catalyzed by N-methyl morpholine (2.5 mol%) to deliver the 3-(cyanomethoxy)acrylates in excellent yields and with preponderance of the E-isomer. The multicomponent reaction manifold is highly tolerant to the structure and composition of the aldehyde (aliphatic, aromatic, heteroaromatics), and it is instrumentally simple (one batch, open atmospheres), economic (2.5 mol% catalyst, stoichiometric reagents), environmentally friendly (no toxic waste), and sustainable (easy scalability).

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Section: Resultsmentioning

confidence: 99%

Cyanovinylation of Aldehydes: Organocatalytic Multicomponent Synthesis of Conjugated Cyanomethyl Vinyl Ethers

2021

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“…Thus, highly specialized equipment is required, complicating the implementation of this chemistry on industrial scales. , Therefore, alternative strategies that rely on less volatile but similarly toxic surrogates ( e.g. , trimethylsilyl cyanide (TMSCN), acetone cyanohydrin) have been employed. − These reagents partially address these safety concerns but fall short of solving the problem since HCN is usually formed in situ . Another challenge associated with the use of HCN in traditional nickel-catalyzed hydrocyanation reactions is the demand for careful adjustment of the HCN concentration to avoid catalyst poisoning through the formation of an inactive nickel dicyanide species, a feature that often complicates scale-up campaigns. ,, …”

Section: Introductionmentioning

confidence: 99%

Development of an Operationally Simple, Scalable, and HCN-Free Transfer Hydrocyanation Protocol Using an Air-Stable Nickel Precatalyst

Reisenbauer

Bhawal

Jelmini

et al. 2022

Org. Process Res. Dev.

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Hydrocyanation reactions enable access to synthetically valuable nitriles from readily available alkene precursors. However, hydrocyanation reactions using hydrogen cyanide (HCN) or similarly toxic reagents on laboratory scale can be particularly challenging due to their hazardous nature. In addition, such processes typically require air-and temperature-sensitive Ni(0) precatalysts, further reducing the operational simplicity of this transformation. Herein, we report a HCN-free transfer hydrocyanation of alkenes and alkynes that employs commercially available aliphatic nitriles as sacrificial HCN donors in combination with a catalytic amount of air-stable and inexpensive NiCl 2 as a precatalyst and a cocatalytic Lewis acid. The scalability and robustness of the catalytic process were demonstrated by the hydrocyanation of α-methylstyrene on a 100 mmol scale (11.4 g of product obtained) using 1 mol % of the Ni catalyst. In addition, the feasibility of the dehydrocyanation protocol using the air-stable Ni(II) precatalyst and norbornadiene as a sacrificial acceptor was showcased by the selective conversion of an aliphatic nitrile into the corresponding alkene.

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Multicomponent Cyanation of 2‐Amino‐3‐cyano‐4H‐chromenes in Aqueous Media

Ardevines,

Garcés‐Marín,

Cervantes‐Cerrada

et al. 2024

Asian J Org Chem

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Chromenes represent a pivotal molecular structure found in a diverse range of biologically active compounds. Specifically, derivatives of 2‐amino‐3‐cyano‐4H‐chromene have demonstrated pharmacological applications, displaying potential antioxidant and anticancer activities. This has heightened interest in the exploration of new and more efficient methods for their synthesis. In recent years, few examples have emerged, focusing on the organocatalytic and enantioselective synthesis of 2‐amino‐3‐cyano‐4H‐chromene derivatives, although the overall number of works to date is limited. In this study, we present the results of the synthesis of 2‐amino‐4H‐chromen‐3,4‐dicarbonitriles through a Michael addition of cyanide to 2‐iminochromenes. To achieve this, we utilized a mild source of cyanide (acetone cyanohydrin), green solvents and catalytic conditions at room temperature, via a multicomponent approach. Furthermore, we initiated the enantioselective study of this process using chiral organocatalysts obtaining promising preliminary results.

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Acetone Cyanohydrin

Cited by 6 publications

References 19 publications

Cyanovinylation of Aldehydes: Organocatalytic Multicomponent Synthesis of Conjugated Cyanomethyl Vinyl Ethers

Cyanovinylation of Aldehydes: Organocatalytic Multicomponent Synthesis of Conjugated Cyanomethyl Vinyl Ethers

Development of an Operationally Simple, Scalable, and HCN-Free Transfer Hydrocyanation Protocol Using an Air-Stable Nickel Precatalyst

Multicomponent Cyanation of 2‐Amino‐3‐cyano‐4H‐chromenes in Aqueous Media

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