The Passerini reaction is a chemical reaction involving an isocyanide, an aldehyde (or ketone), and a carboxylic acid to form a α-acyloxy amide.[1][2][3][4][5] This addition reaction is one of the oldest isocyanide-based multicomponent reactions and was first described in 1921 by Mario Passerini in Florence, Italy.[6][7] It is typically carried out in aprotic solvents but can also be performed in ionic liquids such as water or deep eutectic solvents.[7] It is a third order reaction; first order in each of the reactants. The Passerini reaction is often used in combinatorial and medicinal chemistry with recent utility in green chemistry and polymer chemistry.[6][8][9] As isocyanides exhibit high functional group tolerance, chemoselectivity, regioselectivity, and stereoselectivity, the Passerini reaction has a wide range of synthetic applications.[6][10][11][12]
The Passerini reaction
^Passerini, M.; Simone, L. Gazz. Chim. Ital.1921, 51, 126–29.
^Passerini, M.; Ragni, G. Gazz. Chim. Ital.1931, 61, 964–69.
^Banfi, L.; Riva, R. (2005). The Passerini Reaction. Vol. 65. pp. 1–140. doi:10.1002/0471264180.or065.01. ISBN 978-0471264187. {{cite book}}: |journal= ignored (help).
^Kazemizadeh, A.R.; Ramazani, A. (2012). "Synthetic applications of Passerini reaction". Curr. Org. Chem. 16 (4): 418–450. doi:10.2174/138527212799499868.
^Banfi, L.; Basso, A.; Lambruschini, C.; Moni, L.; Riva, R. (2021). "The 100 facets of the Passerini reaction". Chem. Sci. 12 (47): 15445–15472. doi:10.1039/D1SC03810A. PMC 8654045. PMID 35003575.
^ abcTuten, Bryan T.; Bui, Aaron H.; Wiedbrauk, Sandra; Truong, Vinh X.; Raston, Colin L.; Barner-Kowollik, Christopher (19 August 2021). "Four component Passerini polymerization of bulky monomers under high shear flow". Chemical Communications. 57 (67): 8328–8331. doi:10.1039/D1CC02984C. ISSN 1364-548X. PMID 34323263. S2CID 236498755.
^The Passirini Reaction L. Banfi, R.Riva in Organic Reactions vol. 65 L.E. Overman Ed. Wiley 2005 ISBN 0-471-68260-8
^Taran, Jafar; Ramazani, Ali; Joo, Sang Woo; Ślepokura, Katarzyna; Lis, Tadeusz (2014). "Synthesis of Novel a-(Acyloxy)-a-(quinolin-4-yl)acetamides by a ThreeComponent Reaction between an Isocyanide, Quinoline-4-carbaldehyde, and Arenecarboxylic Acids". Helvetica Chimica Acta. 97: 1088–1096. doi:10.1002/hlca.201300378.
^Wahby, Yasmin; Abdel-Hamid, Hamida; Ayoup, Mohammed Salah (2022). "Two decades of recent advances of Passerini reactions: synthetic and potential pharmaceutical applications". New Journal of Chemistry. 46 (4): 1445–1468. doi:10.1039/D1NJ03832J. ISSN 1144-0546. S2CID 245431805.
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