Tinderholm, Karl

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Abstract. Reported is a cooperative catalytic system consisting of a complex of Pd with dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (XPhos) and the potassium salt of 5-norbornene-2-carboxylic acid that permits the use of epoxides as dual-functionalized alkylating reagents in Catellani-type reactions for the assembly of heterocycles. Steps of the Catellani reaction: Oxidative addition Carbopalladation of norbornene Palladacycle formation Oxidative addition to palladacycle Reductive elimination from palladacycle Norbornene extrusion Termination via Heck reaction, Suzuki reaction, etc. The Catellani reaction is a type of three component reaction in which the Mizoroki-Heck reaction and ortho C-H alkylation with alkyl halide occur concomitantly in the presence of norbornene as a cocatalyst with palladium. General References Catellani, M.; Frignani, F.; Rangoni, A. Angew. Chem. Int. Ed. Engl.

Catellani reaction

Chem. Int. Ed. Engl. 1997, 36, 119. Se hela listan på pubs.rsc.org 2020-11-01 · In this context, the palladium/norbornene (Pd/NBE) cooperative catalysis, also known as Catellani reaction [ 2, 3 ], is capable of the concomitant ortho C–H functionalization and ipso cross-coupling transformation of aryl halides, thus representing one of the most appealing approaches to biaryl scaffolds [ 4 ]. The Catellani reaction is a powerful strategy that allows the expeditious synthesis of highly substituted arenes, which are not easily accessible through traditional transition‐metal‐catalyzed cross‐coupling reactions.

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OL. 2007,5255 32 Addition to CO/CN and CC Bonds Mark Lautens. AICE. 2009,1849 Catellani M. Tetrahedron Lett, 2004(45),6903-6907. 33 Conclusions Catellani reaction is a useful and mechanistically interesting method for the polyfunctionalization of aromatic molecules.

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However, the use of Pd(0) catalysts restricts the scope of accessible products. We have developed a Pd(II)-catalyzed, Catellani-type reaction utilizing arylboronic acids as the substrates for the ﬁrst time. Polyfunctional arenes are essential chemicals with wide-ranging applications.

Key words Catellani reaction, cooperative catalysis, alkyl tosylates, 2018-08-01 · The Catellani reaction enables an ortho-C-H activation based on oxidative addition of Pd(0) and an intermediary carbopalladation of norbornene. Among its variants, the recently developed C2-selective alkylation of indoles is particular as it employs Pd(ii) as the source of palladium. 2019-11-18 · All-carbon tetrasubstituted olefins have been found in numerous biologically important compounds and organic materials. However, regio- and stereocontrolled construction of this structural motif Media in category "Catellani reaction" The following 5 files are in this category, out of 5 total.
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Chem. 2005, 14, 21 2. 2020-11-01 The Catellani reaction is a powerful strategy that allows the expeditious synthesis of highly substituted arenes, which are not easily accessible through traditional transition‐metal‐catalyzed cross‐coupling reactions. This reaction utilizes the synergistic interplay of palladium and norbornene catalysis to facilitate sequential ortho ‐C−H Catellani Reaction. January 2021; DOI: 10.1007/978-3-030-50865-4_24.

This borono-Catellani reaction was promoted by cooperative catalysis between Pd(OAc) 2 and the inexpensive 5-norbornene-2-carbonitrile. Practicality is the striking feature of the reaction: it is run open to air at ambient temperature and no phosphine ligand is needed. Through application of the Catellani reaction, a great number of diverse scaffolds have been synthesized in one pot from simple starting materials. Over the past decade, this methodology has proven useful for the rapid generation of complexity in organic synthesis.
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Over the past decade, this methodology has proven useful for the rapid generation of complexity in organic synthesis. REFERENCES 1. Catellani, M. Top. Organomet. Chem. 2005, 14, 21 2. 2020-11-01 The Catellani reaction is a powerful strategy that allows the expeditious synthesis of highly substituted arenes, which are not easily accessible through traditional transition‐metal‐catalyzed cross‐coupling reactions.