@article{HuangHuShietal.2022,
  author    = {Huang, Mingming and Hu, Jiefeng and Shi, Shasha and Friedrich, Alexandra and Krebs, Johannes and Westcott, Stephen A. and Radius, Udo and Marder, Todd B.},
  title     = {Selective, Transition Metal-free 1,2-Diboration of Alkyl Halides, Tosylates, and Alcohols},
  series = {Chemistry-A European Journal},
  volume    = {28},
  journal   = {Chemistry-A European Journal},
  number    = {24},
  doi       = {10.1002/chem.202200480},
  url       = {http://nbn-resolving.de/urn:nbn:de:bvb:20-opus-318262},
  year      = {2022},
  abstract  = {Defunctionalization of readily available feedstocks to provide alkenes for the synthesis of multifunctional molecules represents an extremely useful process in organic synthesis. Herein, we describe a transition metal-free, simple and efficient strategy to access alkyl 1,2-bis(boronate esters) via regio- and diastereoselective diboration of secondary and tertiary alkyl halides (Br, Cl, I), tosylates, and alcohols. Control experiments demonstrated that the key to this high reactivity and selectivity is the addition of a combination of potassium iodide and N,N-dimethylacetamide (DMA). The practicality and industrial potential of this transformation are demonstrated by its operational simplicity, wide functional group tolerance, and the late-stage modification of complex molecules. From a drug discovery perspective, this synthetic method offers control of the position of diversification and diastereoselectivity in complex ring scaffolds, which would be especially useful in a lead optimization program.},
  language  = {en}
}
@article{HuangHuKrummenacheretal.2022,
  author    = {Huang, Mingming and Hu, Jiefeng and Krummenacher, Ivo and Friedrich, Alexandra and Braunschweig, Holger and Westcott, Stephen A. and Radius, Udo and Marder, Todd B.},
  title     = {Base-Mediated Radical Borylation of Alkyl Sulfones},
  series = {Chemistry—A European Journal},
  volume    = {28},
  journal   = {Chemistry—A European Journal},
  number    = {3},
  doi       = {10.1002/chem.202103866},
  url       = {http://nbn-resolving.de/urn:nbn:de:bvb:20-opus-257281},
  pages     = {e202103866},
  year      = {2022},
  abstract  = {A practical and direct method was developed for the production of versatile alkyl boronate esters via transition metal-free borylation of primary and secondary alkyl sulfones. The key to the success of the strategy is the use of bis(neopentyl glycolato) diboron (B\(_{2}\)neop\(_{2}\)), with a stoichiometric amount of base as a promoter. The practicality and industrial potential of this protocol are highlighted by its wide functional group tolerance, the late-stage modification of complex compounds, no need for further transesterification, and operational simplicity. Radical clock, radical trap experiments, and EPR studies were conducted which show that the borylation process involves radical intermediates.},
  language  = {en}
}