A synthesis of 1,4-diborylated benzenes was achieved by the Ru-catalyzed regioselective co-cyclotrimerization of alkynes with a commercially available ethynyl boronate. The reaction is applicable to a wide array of alkynes with metal-coordinating groups, providing synthetically useful diborylated benzenes in 23-68% isolated yields. DFT calculations shed light on the reaction course and the origin of its remarkable regioselectivity. Selected diborylated benzenes were converted into various products, such as quinones and hydroquinones, including three natural bioactive small molecules.
Selective Catalytic Cross-Cyclotrimerization En Route to 1,4-Diborylated Benzenes and Their Synthetic Transformations
Gabriele Manca;
2023
Abstract
A synthesis of 1,4-diborylated benzenes was achieved by the Ru-catalyzed regioselective co-cyclotrimerization of alkynes with a commercially available ethynyl boronate. The reaction is applicable to a wide array of alkynes with metal-coordinating groups, providing synthetically useful diborylated benzenes in 23-68% isolated yields. DFT calculations shed light on the reaction course and the origin of its remarkable regioselectivity. Selected diborylated benzenes were converted into various products, such as quinones and hydroquinones, including three natural bioactive small molecules.File in questo prodotto:
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prod_476461-doc_194739.pdf
Open Access dal 31/01/2024
Descrizione: "This is the peer reviewed version of the following article: A. A. Fadeev, G. Manca, M. Kotora, Adv. Synth. Catal. 2023, 365, 965, which has been published in final form at https://doi.org/10.1002/adsc.202201337. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions. This article may not be enhanced, enriched or otherwise transformed into a derivative work, without express permission from Wiley or by statutory rights under applicable legislation. Copyright notices must not be removed, obscured or modified. The article must be linked to Wiley’s version of record on Wiley Online Library and any embedding, framing or otherwise making available the article or pages thereof by third parties from platforms, services and websites other than Wiley Online Library must be prohibited."
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Descrizione: Selective Catalytic Cross-Cyclotrimerization En Route to 1,4-Diborylated Benzenes and Their Synthetic Transformations
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