Stable BF$_2$ boracycles as versatile reagents for selective ortho C–H functionalization

Shinde, Ganesh (avtor), Babiker, Jonatan (avtor), Mebrahtu, Michelle (avtor), Prigent, Anaïs (avtor), Foucras, Gauthier (avtor), Aher, Yogesh N. (avtor), Amombo Noa, Francoise M. (avtor), Johansson, Magnus J. (avtor), Košmrlj, Janez (avtor), Jansen-van Vuuren, Ross D. (avtor), Cailly, Thomas (avtor), Sundén, Henrik (avtor)

The development of new boron reagents continues to play a crucial role in advancing modern organic synthesis, particularly in C–H functionalization and cross-coupling reactions. Herein, we report a metal-free, robust, and scalable multigram protocol for the synthesis of stable BF$_2$ boracycles that require no column chromatography, providing a practical and efficient route to access this valuable boron species. The BF$_2$ boracycles exhibit enhanced stability and reactivity, making them highly versatile intermediates for late-stage diversification. They undergo ipso-substitution to afford a wide array of derivatives, including halogenated (e.g., radioiodinated), hydroxylated, and azidated products. Furthermore, they display excellent reactivity in Suzuki–Miyaura cross-coupling reactions, enabling both C(sp$^2$)─C(sp$^2$) and C(sp$^2$)─C(sp$^3$) bond formation. These results underscore the utility of BF$_2$ boracycles as powerful tools for selective functionalization in pharmaceutical synthesis and beyond. Our work represents a significant advancement in organoboron chemistry, offering both a streamlined synthetic approach and broad applicability for complex molecule construction.

• Jezik: Angleški jezik
• Ključne besede: boracycle, ortho functionalization, ipso substitution, pivalamide, radioiodination, O-carbamates, phenols, multigram scale
• Vrsta gradiva: Članek v reviji
• Tipologija: 1.01 - Izvirni znanstveni članek
• Organizacija: FKKT - Fakulteta za kemijo in kemijsko tehnologijo
• Status publikacije: Objavljeno
• Različica publikacije: Objavljena publikacija
• Leto izida: 2026
• Št. strani: 9 str.
• Številčenje: Vol. 65, iss. 8, art. e18421
• PID: 20.500.12556/RUL-181101
• UDK: 547.1.057:546.27
• ISSN pri članku: 1433-7851
• DOI: 10.1002/anie.202518421
• COBISS.SI-ID: 265701123
• Datum objave v RUL: 25.03.2026

Gradivo je del revije

• Naslov: Angewandte Chemie : International edition
• Skrajšan naslov: Angew. Chem.
• Založnik: Wiley-VCH
• ISSN: 1433-7851
• COBISS.SI-ID: 18592005

Licence

• Licenca: CC BY 4.0, Creative Commons Priznanje avtorstva 4.0 Mednarodna
• Povezava: http://creativecommons.org/licenses/by/4.0/deed.sl
• Opis: To je standardna licenca Creative Commons, ki daje uporabnikom največ možnosti za nadaljnjo uporabo dela, pri čemer morajo navesti avtorja.

Sekundarni jezik

• Jezik: Slovenski jezik
• Ključne besede: boracikel, orto funkcionalizacija, ipso substitucija, pivalamid, radiojodiranje, O-karbamati, fenoli, multigramska lestvica