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Published on: November 9, 2019
Stable BF2 Boracycles as Versatile Reagents for Selective Ortho C-H Functionalization
Ganesh H Shinde1, Jonatan Babiker1, Michelle Mebrahtu1
1Department of Chemistry and Molecular Biology, University of Gothenburg, Gothenburg, Sweden, SE-41296.
Abstract:
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 BF2 boracycles that require no column chromatography, providing a practical and efficient route to access this valuable boron species. The BF2 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(sp2)─C(sp2) and C(sp2)─C(sp3) bond formation. These results underscore the utility of BF2 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.
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