Closing the Cycle as It Begins: Synthesis of ortho‐Iodobiaryls via Catellani Reaction

Author:

Botla Vinayak1,Fontana Marco1,Voronov Aleksandr1,Maggi Raimondo1,Motti Elena1,Maestri Giovanni1,Della Ca' Nicola1ORCID

Affiliation:

1. Department of Chemistry Life Sciences and Environmental Sustainability (SCVSA) University of Parma Parco Area delle Scienze, 17/A 43124 Parma Italy

Abstract

AbstractDespite the advances in the field of carbon‐halogen bond formation, the straightforward catalytic access to selectively functionalized iodoaryls remains a challenge. Here, we report a one‐pot synthesis of ortho‐iodobiaryls from aryl iodides and bromides by palladium/norbornene catalysis. This new example of Catellani reaction features the initial cleavage of a C(sp2)−I bond, followed by the key formation of a palladacycle through ortho C−H activation, the oxidative addition of an aryl bromide and the ultimate restoration of the C(sp2)−I bond. A large variety of valuable o‐iodobiaryls has been synthesized in satisfactory to good yields and their derivatization have been described too. Beyond the synthetic utility of this transformation, a DFT study provides insights on the mechanism of the key reductive elimination step, which is driven by an original transmetallation between palladium(II)‐halides complexes.

Funder

H2020 Marie Skłodowska-Curie Actions

Università degli Studi di Parma

Publisher

Wiley

Subject

General Medicine

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