20.500.12556/RUL-181101 Stable BF$_2$ boracycles as versatile reagents for selective ortho C–H functionalization 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. boracycle ortho functionalization ipso substitution pivalamide radioiodination O-carbamates phenols multigram scale boracikel orto funkcionalizacija ipso substitucija pivalamid radiojodiranje O-karbamati fenoli multigramska lestvica true false true Angleški jezik Slovenski jezik Članek v reviji 2026-03-25 09:10:03 2026-03-25 09:10:21 2026-03-26 04:21:47 0000-00-00 00:00:00 2026 0 0 9 str. iss. 8, art. e18421 Vol. 65 16 Feb. 2026 0000-00-00 Zaloznikova Objavljeno NiDoloceno 0000-00-00 0000-00-00 0000-00-00 547.1.057:546.27 1433-7851 10.1002/anie.202518421 265701123 RAZ_Shinde_Ganesh_2026.pdf RAZ_Shinde_Ganesh_2026.pdf 1 9B5D8FBB8D690CACA7B753BD2601F635 06a72afef9b7aafa0cc7b9725b42686791a038802da66a5546fbdd8556db0efb 811c4045-2823-11f1-b0ab-0050569b8976 https://repozitorij.uni-lj.si/Dokument.php?lang=slv&id=231279 https://onlinelibrary.wiley.com/doi/10.1002/anie.202518421 1 f2d65855-2821-11f1-b0ab-0050569b8976 https://repozitorij.uni-lj.si/Dokument.php?lang=slv&id=231275 Fakulteta za kemijo in kemijsko tehnologijo 0 0 0