Pd-Catalyzed C–O Bond Formation: Coupling of Aryl Boronic Acids with O-Electrophiles

Pd-Catalyzed C–O Bond Formation: Coupling of Aryl Boronic Acids with O-Electrophiles Научная публикация

Журнал

ACS Catalysis
ISSN: 2155-5435

Вых. Данные

Год: 2025, Том: 15, Номер: 5, Страницы: 3636-3646 Страниц : 11 DOI: 10.1021/acscatal.4c07285

Авторы

Vil’ Vera A. ¹ , Barsegyan Yana A. ¹ , Chabuka Beauty K. ² , Ilovaisky Alexey I. ¹ , Alabugin Igor V. ² , Terent’ev Alexander O. ¹

Организации

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prospect, Moscow 119991, Russian Federation
2	Department of Chemistry and Biochemistry, Florida State University, Tallahassee, Florida 32306, United States

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.

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

Web of science:	WOS:001422591600001
OpenAlex:	W4407561221

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