Synthetic applications of the Cannizzaro reaction

• Bhaskar Chatterjee,
• Dhananjoy Mondal and
• Smritilekha Bera

Beilstein J. Org. Chem. 2024, 20, 1376–1395, doi:10.3762/bjoc.20.120

• Bhaskar Chatterjee Dhananjoy Mondal Smritilekha Bera Department of Chemistry, Nabadwip Vidyasagar College, West Bengal, India School of Chemical Sciences, Central University of Gujarat, Gandhinagar-382030, India 10.3762/bjoc.20.120 Abstract The Cannizzaro reaction has emerged as a versatile

• , solvents, and technologies for the Cannizzaro reaction reflects the broader trend in organic synthesis towards more sustainable and efficient practices. The focus of this review is to highlight some recent advances in synthetic strategies and applications of the Cannizzaro reaction towards the synthesis of

• potentially useful molecules. Keywords: Cannizzaro reaction; crossed-Cannizzaro; desymmetrization; Lewis acid catalyst; natural products; Introduction The synthesis of functionalized molecules with structural complexity has always been a challenge to synthetic chemists. The Cannizzaro reaction, in its

On Reuben G. Jones synthesis of 2-hydroxypyrazines

• Pierre Legrand and
• Yves L. Janin

Beilstein J. Org. Chem. 2022, 18, 935–943, doi:10.3762/bjoc.18.93

• bond thus confirming an oxo-bearing tautomeric form adopted in the solid state. Concerning the mechanism of this double condensation, the interpretation of the experimental results must take into account two very likely side reactions. The first one would be a Cannizzaro reaction which, from the

Formose reaction controlled by boronic acid compounds

• Toru Imai,
• Tomohiro Michitaka and
• Akihito Hashidzume

Beilstein J. Org. Chem. 2016, 12, 2668–2672, doi:10.3762/bjoc.12.263

• formose reaction consists of several elemental reaction steps, e.g., acyloin condensation, aldol reaction, retro-aldol reaction, aldose–ketose isomerization, and Cannizzaro reaction, and the product, formose, is a complicated mixture of more than thirty species of sugars and sugar alcohols including non

Formose reaction accelerated in aerosol-OT reverse micelles

• Makoto Masaoka,
• Tomohiro Michitaka and
• Akihito Hashidzume

Beilstein J. Org. Chem. 2016, 12, 2663–2667, doi:10.3762/bjoc.12.262

• transformation in the sugar formation period. When formaldehyde is consumed quantitatively, the reaction mixture turns yellow. In the sugar degradation period, the sugars formed are decomposed dominantly through cross-Cannizzaro reaction and retro-aldol reaction to form a more complicated reaction mixture. The

• Cannizzaro reaction. (We could not assign the signal at ca. 75 ppm comparing to signals for various sugar and sugar alcohols.) On the basis of these spectra, we can conclude that ethylene glycol is formed as a major product. In summary, the formose reaction in reverse micelles of AOT, TX, and CTAB was

Chemoselective reduction of aldehydes by ruthenium trichloride and resin- bound formates

• Basudeb Basu,
• Bablee Mandal,
• Sajal Das,
• Pralay Das and
• Ashis K. Nanda

Beilstein J. Org. Chem. 2008, 4, No. 53, doi:10.3762/bjoc.4.53

• without any base preclude possibilities of unwanted reactions of aryl aldehydes, e.g. Cannizzaro reaction. To broaden the scope of the catalytic system, we tested CTH of 1,2-diketones under similar conditions (Scheme 2). Whereas aryl ketones were not reduced under the conditions, reduction of benzil to