Carbon–Carbon Bond Cleavage and Esterification of Phenylacetonitrile and its Derivatives Affording the Corresponding Benzoic Esters

Wang, Zhiyuan; Kang, Junhui; Yu, Mingxin

doi:10.3184/030823407x218110

Cited by 7 publications

(2 citation statements)

References 17 publications

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“…Phenylmethyl 3‐Nitrobenzote (3de): The reaction of 3‐nitrobenzaldehyde (157.8 mg, 1.044 mmol) and benzyl alcohol (36.05 µL, 0.348 mmol) was carried out by employing the general procedure described above to afford 3de (60 % yield based on methanol by 1 H NMR spectroscopy). Purification by flash chromatography on silica gel ( n ‐hexane/EtOAc, 20:1) gave 3de (38 mg, 42 % isolated yield) as an off‐white solid.…”

Section: Methodsmentioning

confidence: 99%

Facile Coupling of Aldehydes with Alcohols: An Evolved Tishchenko Process for the Preparation of Unsymmetrical Esters

Liu

Eisen

2017

Eur J Org Chem

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A facile coupling process between aldehydes and alcohols to afford unsymmetrical esters is presented herein. This transformation is complementary to the Tishchenko reaction and provides access to unsymmetrical esters under very mild conditions. Various aldehydes and alcohols are suitable in this reaction, and the addition of a sacrificial trifluoromethyl ketone allows the process to take place in a highly selective manner. A plausible mechanism based on details obtained by monitoring the reaction progress and deuterium‐labeling studies has been proposed.

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Section: Methodsmentioning

confidence: 99%

Facile Coupling of Aldehydes with Alcohols: An Evolved Tishchenko Process for the Preparation of Unsymmetrical Esters

Liu

Eisen

2017

Eur J Org Chem

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“…For instance, Yu and his co-workers first reported a novel C–CN bond cleavage reaction in arylacetonitriles to afford aryl carboxylic esters by using Samarium as catalyst in one-pot process . After that, iodine was used as a catalyst for this conversion reported later by the same authors as part of their continuation of these studies . However, their transformations are greatly restricted due to the dependence on strong electron-withdrawing substituents on the aromatic rings (such as the nitro group) (Scheme a).…”

Section: Introductionmentioning

confidence: 99%

Fe-Catalyzed Aerobic Oxidative C–CN Bond Cleavage of Arylacetonitriles Leading to Various Esters

Kong

et al. 2016

J. Org. Chem.

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Fe-catalyzed aerobic oxidative esterifications of arylacetonitriles with alcohols, tri alkoxsilanes, silicate esters, or borate esters have been developed. The acyl groups which were in situ generated via chemoselective C(CO)-CN bond cleavage were directly used as electrophiles, leading to corresponding aryl esters in good to excellent yields under molecular oxygen when attacked by alcohols or alcohol surrogates. Dioxygen serves as both oxidant and reactant in this protocol. The reaction has a very broad substrate scope. Cheap starting materials as well as environmentally benign and inexpensive iron catalyst and ideal oxidant O2 feature this transformation and make it a practical and sustainable protocol to afford esters.

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Copper‐mediated simple and direct aerobic oxidative esterification of arylacetonitriles with alcohols/phenols

Dong

Chen

et al. 2020

Applied Organom Chemis

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A simple and direct aerobic oxidative esterification reaction of arylacetonitriles with alcohols/phenols is achieved in the presence of a copper salt and molecular oxygen, which produces a broad range of aryl carboxylic acid esters in good to high yields. Copper salt plays multiple roles in the transformation, which allows the oxygenation of C H bond, cleavage of inert C C bond, and formation of C O bond in one pot without the assistance of any of the acids, bases, ligands, and so on. The reaction provides a simple, direct, and efficient protocol towards functionalized esters, especially aryl benzoates, from readily available starting materials.

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Carbon–Carbon Bond Cleavage and Esterification of Phenylacetonitrile and its Derivatives Affording the Corresponding Benzoic Esters

Cited by 7 publications

References 17 publications

Facile Coupling of Aldehydes with Alcohols: An Evolved Tishchenko Process for the Preparation of Unsymmetrical Esters

Facile Coupling of Aldehydes with Alcohols: An Evolved Tishchenko Process for the Preparation of Unsymmetrical Esters

Fe-Catalyzed Aerobic Oxidative C–CN Bond Cleavage of Arylacetonitriles Leading to Various Esters

Copper‐mediated simple and direct aerobic oxidative esterification of arylacetonitriles with alcohols/phenols

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