1. Closing the Cycle as It Begins: Synthesis of ortho‐Iodobiaryls via Catellani Reaction.
- Author
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Botla, Vinayak, Fontana, Marco, Voronov, Aleksandr, Maggi, Raimondo, Motti, Elena, Maestri, Giovanni, and Della Ca', Nicola
- Subjects
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ARYL iodides , *OXIDATIVE addition , *PALLADIUM , *ARYL bromides , *DERIVATIZATION - Abstract
Despite 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. [ABSTRACT FROM AUTHOR]
- Published
- 2023
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