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Synfacts 2025; 21(10): 1005
DOI: 10.1055/a-2680-8867
DOI: 10.1055/a-2680-8867
Metals in Synthesis
Oxygenative Suzuki–Miyaura Cross-Coupling to Access Diaryl Ethers
Authors
Jiang Y,
Kwan EE,
Ping Y,
Liu RY *.
Harvard University, Cambridge, USA
Synthesis of Diaryl Ethers by Formal Oxygen Insertion Between Suzuki–Miyaura Coupling Partners.
ACS Catal. 2025;
15: 13588-13594
DOI: 10.1021/acscatal.5c03249
Synthesis of Diaryl Ethers by Formal Oxygen Insertion Between Suzuki–Miyaura Coupling Partners.
ACS Catal. 2025;
15: 13588-13594
DOI: 10.1021/acscatal.5c03249
Significance
Liu and co-workers disclosed a three-component cross-coupling protocol to access diaryl ethers by formally inserting an oxygen atom into a Suzuki–Miyaura cross-coupling reaction. This method involves the in situ oxidation of the aryl boronic acid using N-methylmorpholine N-oxide (NMO) as the oxidant.
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Comment
Mechanistic studies revealed that a high NMO concentration inhibits the reaction by Lewis adduct formation with in situ formed Ar2OBpin. However, the byproduct, N-methylmorpholine (NMM), was found to accelerate the ligand exchange between Ar1[Pd]X and Ar2OBpin.
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Publikationsverlauf
Artikel online veröffentlicht:
23. September 2025
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