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General References Catellani, M.; Frignani, F.; Rangoni, A. Angew. Chem. Int. Ed. Engl. 1997, 36, 119.

Catellani reaction

Under previous conditions, unhindered aryl halides were plagued with the formation of simple Heck isomers and multiple arylation and norbornene insertion. The use of a bulky P t Bu 3 ligand Norbornene is used in the Catellani reaction and in norbornene-mediated meta-C−H activation. Norbornene - Wikipedia Marta Catellani is an Italian chemist known for her discovery of the eponymous Catellani reaction in 1997. 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 Reported is a novel palladium(II)-initiated Catellani-type reaction that utilizes widely accessible aryl boronic acids as the substrates instead of aryl halides, thereby greatly expanding the existing scope of this powerful transformation. This borono-Catellani reaction was promoted by cooperative c … Abstract A palladium-catalyzed and norbornene-mediated Catellani reaction was developed through ortho-acylation and ipso-alkynylation for the aryl iodides.

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REFERENCES 1. Catellani, M. Top. Organomet.

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She was elected to the European Academy of Sciences in 2016.

46 The C2 ethyl ester-substituted N21* gave the highest enantioselectivity (96% ee), while the methylamide-substituted N12* afforded 86% ee and diminished reactivity. Media in category "Catellani reaction" The following 5 files are in this category, out of 5 total.
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General References Catellani, M.; Frignani, F.; Rangoni, A. Angew. Chem. Int. Ed. Engl.

In book: Name Reactions (pp.73-76) Authors: Jie Jack Li. Request full-text PDF The Catellani reaction is known as a powerful strategy for the expeditious synthesis of highly substituted arenes and benzo‐fused rings, which are usually difficult to access through traditional cross‐coupling strategies. It utilizes the synergistic interplay of palladium and norbornene catalysis to facilitate sequential ortho C−H functionalization 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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Typical procedure for isolation: In an argon-filled glove box, a dry 10-mL Schlenk tube containing a magnetic stirbar was charged with Pd(dba) 2 (11.5 mg, 0.02 mmol), PtBu 3 ·HBF 4 (11.5 mg, 0.03 mmol) and dry DMF (1.0 mL). After stirring at RT for 10 These intermediates have been a long-standing focus of the Catellani-reaction development, but persistent challenges have given rise to the well-known “ ortho effect.” We now show that the ortho effect can be a positive element of reaction design, and that previously problematic iodides can now be used in complexity-generating transformations. These intermediates have been a long-standing focus of the Catellani-reaction development, but persistent challenges have given rise to the well-known “ ortho effect.” We now show that the ortho effect can be a positive element of reaction design, and that previously problematic iodides can now be used in complexity-generating transformations.

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OL. 2004,4759 Mark Lautens. 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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B) Enabling gas–liquid Catellani reactions through a continuous‐flow platform. Historically, Catellani reactions have been limited to liquid or solid reagents.