Pd-Catalyzed C–O Bond Formation: Coupling of Aryl Boronic Acids with O-Electrophiles Full article
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ACS Catalysis
ISSN: 2155-5435 |
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Output data | Year: 2025, Volume: 15, Number: 5, Pages: 3636-3646 Pages count : 11 DOI: 10.1021/acscatal.4c07285 | ||||
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Abstract:
Due to the scarcity of practically useful O-electrophiles, Suzuki-type C–O coupling is far less common than the well-established C–C coupling. In this work, we introduce cyclic diacyl peroxides as effective O-electrophiles for cross-coupling with boronic acids, a process that likely proceeds via a Pd(II)/Pd(IV) catalytic cycle. The success of this method can be attributed to the higher oxidative potential of cyclic diacyl peroxides and the ability to avoid the elimination of CO2 in high-valent Pd intermediates. Additionally, the Pd(IV) complex with cyclic diacyl peroxide maintains a ground state singlet spin state with no radical character on the acetate and carboxylate ligands that facilitate the transmetalation step. The reaction produces a variety of aryl esters with an additional carboxylic acid group as a platform for further functionalization.
Cite:
Vil’ V.A.
, Barsegyan Y.A.
, Chabuka B.K.
, Ilovaisky A.I.
, Alabugin I.V.
, Terent’ev A.O.
Pd-Catalyzed C–O Bond Formation: Coupling of Aryl Boronic Acids with O-Electrophiles
ACS Catalysis. 2025. V.15. N5. P.3636-3646. DOI: 10.1021/acscatal.4c07285 WOS OpenAlex
Pd-Catalyzed C–O Bond Formation: Coupling of Aryl Boronic Acids with O-Electrophiles
ACS Catalysis. 2025. V.15. N5. P.3636-3646. DOI: 10.1021/acscatal.4c07285 WOS OpenAlex
Identifiers:
Web of science: | WOS:001422591600001 |
OpenAlex: | W4407561221 |
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