CuI-Zeolite Catalysis for Biaryl Synthesis via Homocoupling Reactions of Phenols or Aryl Boronic Acids - Archive ouverte HAL
Article Dans Une Revue Molecules Année : 2024

CuI-Zeolite Catalysis for Biaryl Synthesis via Homocoupling Reactions of Phenols or Aryl Boronic Acids

Résumé

Due to the importance of biaryls as natural products, drugs, agrochemicals, dyes, or organic electronic materials, a green alternative biaryl synthesis has been developed based on easy-to-prepare and cheap copper(I)-exchanged zeolite catalysts. CuI-USY proved to efficiently catalyze the direct homocoupling of either phenols or aryl boronic acids under simple and practical conditions. The CuI-USY-catalyzed oxidative homocoupling of phenols could conveniently be performed under air either in warm methanol or water with good to high yields. In methanol, a small amount of Cs2CO3 was required, while none was necessary in water. The homocoupling of aryl boronic acids was best performed also in warm methanol, without an additive. These mild conditions showed good functional-group tolerance, leading to a variety of substituted (hetero)biaryls (28 examples). The heterogeneous CuI-USY catalyst could readily be recovered and reused. Interestingly, the homocoupling of vinyl boronic acids was successfully coupled to a Diels–Alder reaction, even in a one-pot process, allowing access to highly functionalized cyclohexenes.

Domaines

Chimie

Dates et versions

hal-04844871 , version 1 (18-12-2024)

Identifiants

Citer

Xiaohui Di, Tony Garnier, Arnaud Clerc, Eliott Jung, Christian Lherbet, et al.. CuI-Zeolite Catalysis for Biaryl Synthesis via Homocoupling Reactions of Phenols or Aryl Boronic Acids. Molecules, 2024, 29 (23), pp.5552. ⟨10.3390/molecules29235552⟩. ⟨hal-04844871⟩
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