Synthesis of Chiral-Substituted 2-Aryl-ferrocenes by the Catellani Reaction A palladium-catalyzed and norbornene-mediated methodology has been developed for the synthesis of chiral 2-aryl-ferroceneamides from chiral 2-iodo-N,N-diisopropylferrocencarboxamide, iodoarenes, and alkenes using a JohnPhos ligand and potassium carbonate as a base in dimethylformamide at 105 °C.

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.

We called 18 Nov 2019 However, such an alkenyl Catellani reaction remains underexplored, In the 1980s, Catellani and co-workers found that reactions of alkenyl 30 Jan 2020 Key words. Catellani reaction - cooperative catalysis - alkyl tosylates - 5- norbornene-2-carbonitrile - polysubstituted arenes 18 Feb 2021 An unprecedented atroposelective Catellani reaction between phosphine oxide- containing aryl bromides, aryliodides, and nucleophiles for the Download scientific diagram | Scheme 4. Key step: Catellani reaction. a) Pd(OAc) 2 (10 mol %), PPh3 (22 mol %), norbornene, Cs2CO3, DMF (sealed tube), 2021年1月22日 The Catellani reaction, originally discovered by Catellani in 1997, and further developed by Catellani, Lautens and others, has emerged as a A new reaction sequence involving palladium-catalyzed unsymmetrical aryl coupling. F Faccini, E Motti, M Catellani.

Catellani reaction

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.

Request PDF | Modular and regioselective synthesis of all-carbon tetrasubstituted olefins enabled by an alkenyl Catellani reaction | All-carbon tetrasubstituted olefins have been found in numerous 2015-11-01 2019-11-18 2009-10-14 2013-12-17 Alkyl Tosylates as Alkylating Reagents in the Catellani Reaction Qianwen Gao a Sauvage Center for Molecular Sciences, Engineering Research Center of Organosilicon Compounds & Materials (Ministry of Education), College of Chemistry and Molecular Sciences, Wuhan University, 430072 Wuhan, P. R. of China Email: hgcheng@whu.edu.cn Email: qhzhou@whu.edu.cn We report a cooperative catalytic system comprising a PdII complex, XPhos, and the potassium salt of 5‐norbornene‐2‐carboxylic acid that enables the use of epoxides as alkylating reagents in the Catellani reaction, thereby expanding the existing paradigm of this powerful transformation.

The process allowed for the construction of up to three carbon-carbon bonds in a single reaction using simple, commercially available starting materials. We called

The termination step is flexible, which is demonstrated by ipso-Heck reaction, hydrogenation, Suzuki coupling, and Sonogashira coupling. A 4-component Catellani reaction affords an efficient synthesis of substituted arenes • The well-known ortho effect is used as a constructive element of reaction design • Predictable chemo- and regioselectivity result from subtle substituent effects • Atom and step economic synthesis of polyfunctional arenes In conclusion, we successfully realized the first vinylogous Catellani reaction of 4-iodo-2-quinolones with benzyl alcohols bearing a tertiary benzyl moiety.

Synthesis of Chiral-Substituted 2-Aryl-ferrocenes by the Catellani Reaction A palladium-catalyzed and norbornene-mediated methodology has been developed for the synthesis of chiral 2-aryl-ferroceneamides from chiral 2-iodo-N,N-diisopropylferrocencarboxamide, iodoarenes, and alkenes using a JohnPhos ligand and potassium carbonate as a base in dimethylformamide at 105 °C.

Modular and Stereoselective Synthesis of C-Aryl Glycosides via Catellani Reaction | Journal of the American Chemical Society. In this work, we describe a Catellani-type C–H glycosylation to provide rapid access to various highly decorated α-C-(hetero)aryl glycosides in a modular and stereoselective manner (>90 examples).

2- Modified Catellani’s Reaction: Marc and Christophe 3- Rhodium Chemistry: Raphaël, Romain and Sébastien 4- Cyclopropanes Chemistry: Thomas and Corinne 5- Oxa- and Azabicycles Ring Opening: Marie-Alice, Mathieu and Aurélie Palladium (II)‐Initiated Catellani‐Type Reactions.
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We report a cooperative catalytic system comprising a Pd II complex, XPhos, and the potassium salt of 5‐norbornene‐2‐carboxylic acid that enables the use of epoxides as alkylating reagents in the Catellani reaction, thereby expanding the existing paradigm of this powerful transformation. In this work, we describe a Catellani-type C–H glycosylation to provide rapid access to various highly decorated α-C-(hetero)aryl glycosides in a modular and stereoselective manner (>90 examples).

Historically, Catellani reactions have been limited to liquid or solid reagents. This can be ascribed to the fact that the use of gaseous olefins has long been avoided due to safety concerns (i.e., pressurized headspace and leakages) and process constraints (i.e., gas–liquid mass‐transfer limitations).
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Reaction mechanism []. The Catellani reaction is catalyzed by palladium and norbornene, although in most cases superstochiometric amounts of norbornene are used to allow the reaction to proceed at a reasonable rate. The generally accepted reaction mechanism, as outlined below, is intricate and believed to proceed via a series of Pd(0), Pd(II), and Pd(IV) intermediates, although an alternative

Thieme E-Books & E-Journals. 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.