The Catellani reaction was discovered by Marta Catellani (Università degli Studi di Parma, Italy) and co-workers in 1997.[1][2] The reaction uses aryl iodides to perform bi- or tri-functionalization, including C-H functionalization of the unsubstituted ortho position(s), followed a terminating cross-coupling reaction at the ipso position. This cross-coupling cascade reaction depends on the ortho-directing transient mediator, norbornene.
Original and general reaction conditions for the Catellani reaction. PNP2 = cis,exo-2-phenylnorbornyl palladium chloride dimerCatalytic cycle of the Catellani reaction.[3] (Ligands and stereochemistry are omitted for clarity.)
^Catellani, Marta; Frignani, Franco; Rangoni, Armando (1997-02-03). "A Complex Catalytic Cycle Leading to a Regioselective Synthesis of o,o′-Disubstituted Vinylarenes". Angewandte Chemie International Edition in English. 36 (1–2): 119–122. doi:10.1002/anie.199701191. ISSN 1521-3773.
^Catellani; et al. (1997). "Regioselektive Synthese o,o′-disubstituierter Vinylarene über einen komplexen Katalysecyclus". Angewandte Chemie. 109 (1–2): 142–145. doi:10.1002/ange.19971090146.
^Martins; et al. (2010). "Synthesis in the Key of Catellani: Norbornene-Mediated ortho C–H Functionalization". C-H Activation. Topics in Current Chemistry. Vol. 292. pp. 1–33. doi:10.1007/128_2009_13. ISBN 978-3-642-12355-9. PMID 21500401.
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