Stable BF2 Boracycles as Versatile Reagents for Selective Ortho C–H Functionalization
Journal article, 2026
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.
BBr3
Radioiodination
Boron
Late-stage functionalization
Cross-coupling
Author
Ganesh H. Shinde
University of Gothenburg
Jonatan Babiker
University of Gothenburg
Michelle Mebrahtu
University of Gothenburg
Anaïs Prigent
Centre François Baclesse
CERMN - Centre d'Etudes et de Recherche sur le Médicament de Normandie
Gauthier Foucras
Centre François Baclesse
CERMN - Centre d'Etudes et de Recherche sur le Médicament de Normandie
Yogesh N. Aher
University of Gothenburg
Francoise Mystere Amombo Noa
Chalmers, Chemistry and Chemical Engineering, Chemistry and Biochemistry
Magnus J. Johansson
AstraZeneca AB
Janez Košmrlj
University of Ljubljana
Ross D. Jansen-van Vuuren
University of Ljubljana
Thomas Cailly
Institut Blood and Brain @ Caen Normandie (BB@C)
Normandie University
Hopital Cote de Nacre
CERMN - Centre d'Etudes et de Recherche sur le Médicament de Normandie
Henrik Sundén
University of Gothenburg
AstraZeneca AB
Angewandte Chemie
14337851 (ISSN) 15213773 (eISSN)
Vol. In PressSubject Categories (SSIF 2025)
Organic Chemistry
DOI
10.1002/anie.202518421