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

• in subsequent reactions. Reddy and coworkers carried out the Cannizzaro reaction of aromatic aldehydes to the corresponding alcohols in high yields by crossed-Cannizzaro reactions employing solid-supported KF-Al2O3 as catalyst [26] under microwave irradiation using solvent-free conditions. The use of

Addition of H-phosphonates to quinine-derived carbonyl compounds. An unexpected C9 phosphonate–phosphate rearrangement and tandem intramolecular piperidine elimination

• Łukasz Górecki,
• Artur Mucha and
• Paweł Kafarski

Beilstein J. Org. Chem. 2014, 10, 883–889, doi:10.3762/bjoc.10.85

• observed reactivity seemed to be general as formation of compound 13b was evidenced (to a different extent) in other variants of the catalytical addition of diethyl phosphite to quininone/quinidinone, with catalytic systems such as: KF/Al2O3, NH3/EtOH and DBU/EtOH or toluene. Independent of the catalyst

Reactions of salicylaldehyde and enolates or their equivalents: versatile synthetic routes to chromane derivatives

• Ishmael B. Masesane and
• Zelalem Yibralign Desta

Beilstein J. Org. Chem. 2012, 8, 2166–2175, doi:10.3762/bjoc.8.244

• of salicylaldehyde (5) with dimedone (18) in the presence of a catalytic amount of KF/Al2O3 (Scheme 6) [21]. The reaction is thought to proceed through a Knoevenagel condensation, a Michael addition and an intramolecular cyclization. The reaction was repeated with chloro-, bromo-, dichloro-, dibromo

Michael-type addition of azoles of broad-scale acidity to methyl acrylate

• Sławomir Boncel,
• Kinga Saletra,
• Barbara Hefczyc and
• Krzysztof Z. Walczak

Beilstein J. Org. Chem. 2011, 7, 173–178, doi:10.3762/bjoc.7.24

• protocol and a simple work-up. In the Michael-type additions of azole N–H acids, numerous catalysts such as KF/Al2O3 [8], CeCl3∙7 H2O/NaI [9], NaH or ZnCl2 [10], K2CO3 [11], anhydrous K3PO4 [12], (NH4)2Ce(NO3)6 (CAN) [22] or ionic liquids, e.g., Cu(acac)2 immobilised in [bmim][BF4] [15] have been used

Solvent-free and time-efficient Suzuki–Miyaura reaction in a ball mill: the solid reagent system KF–Al₂O₃ under inspection

• Franziska Bernhardt,
• Ronald Trotzki,
• Tony Szuppa,
• Achim Stolle and
• Bernd Ondruschka

Beilstein J. Org. Chem. 2010, 6, No. 7, doi:10.3762/bjoc.6.7

• the above mentioned parameters on the results of coupling reactions. The results from ball milling experiments led to the conclusion that self-prepared and commercially available KF–Al2O3 differ in water content. The higher the residual water content, the higher are the product yields. Keywords: ball

• milling; C–C coupling; KF–Al2O3; palladium; solid reagent system; Introduction Over the last two decades, a major trend in the field of organic chemistry has been evident: environmentally friendly processes using safer reagents, generating fewer side products and requiring less use of solvents are in

• vogue [1][2]. This trend has led to an explosive growth in the fields of solvent-free synthesis [3][4][5][6][7][8][9][10][11][12][13] and solid-supported reagents [14][15][16][17][18] such as potassium fluoride on alumina (KF–Al2O3) [19][20]. This versatile reagent was originally introduced in 1979 by