Stable BF$_2$ boracycles as versatile reagents for selective ortho C–H functionalizationShinde, 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) boracycleortho functionalizationipso substitutionpivalamideradioiodinationO-carbamatesphenolsmultigram scaleThe 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.20262026-03-25 09:10:03Članek v reviji181101sl