In:
Angewandte Chemie, Wiley, Vol. 135, No. 18 ( 2023-04-24)
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(sp 2 )−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(sp 2 )−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.
Type of Medium:
Online Resource
ISSN:
0044-8249
,
1521-3757
DOI:
10.1002/ange.v135.18
DOI:
10.1002/ange.202218928
Language:
English
Publisher:
Wiley
Publication Date:
2023
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