@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{LiuBudimanTianetal.2020,
  author    = {Liu, Zhiqiang and Budiman, Yudha P. and Tian, Ya-Ming and Friedrich, Alexandra and Huang, Mingming and Westcott, Stephen A. and Radius, Udo and Marder, Todd B.},
  title     = {Copper-Catalyzed Oxidative Cross-Coupling of Electron-Deficient Polyfluorophenylboronate Esters with Terminal Alkynes},
  series = {Chemistry - A European Journal},
  volume    = {26},
  journal   = {Chemistry - A European Journal},
  number    = {71},
  doi       = {10.1002/chem.202002888},
  url       = {http://nbn-resolving.de/urn:nbn:de:bvb:20-opus-224362},
  pages     = {17267 -- 17274},
  year      = {2020},
  abstract  = {We report herein a mild procedure for the copper-catalyzed oxidative cross-coupling of electron-deficient polyfluorophenylboronate esters with terminal alkynes. This method displays good functional group tolerance and broad substrate scope, generating cross-coupled alkynyl(fluoro)arene products in moderate to excellent yields. Thus, it represents a simple alternative to the conventional Sonogashira reaction.},
  language  = {en}
}
@article{LiuMingLuoetal.2020,
  author    = {Liu, Xiaocui and Ming, Wenbo and Luo, Xiaoling and Friedrich, Alexandra and Maier, Jan and Radius, Udo and Santos, Webster L. and Marder, Todd B.},
  title     = {Regio- and Stereoselective Synthesis of 1,1-Diborylalkenes via Br{\o}nsted Base-Catalyzed Mixed Diboration of Alkynyl Esters and Amides with BpinBdan},
  series = {European Journal of Organic Chemistry},
  volume    = {2020},
  journal   = {European Journal of Organic Chemistry},
  number    = {13},
  doi       = {10.1002/ejoc.202000128},
  url       = {http://nbn-resolving.de/urn:nbn:de:bvb:20-opus-214728},
  pages     = {1941 -- 1946},
  year      = {2020},
  abstract  = {The NaOtBu-catalyzed mixed 1,1-diboration of terminal alkynes using the unsymmetrical diboron reagent BpinBdan (pin = pinacolato; dan = 1,8-diaminonaphthalene) proceeds in a regio- and stereoselective fashion affording moderate to high yields of 1,1-diborylalkenes bearing orthogonal boron protecting groups. It is applicable to gram-scale synthesis without loss of yield or selectivity. The mixed 1,1-diborylalkene products can be utilized in Suzuki-Miyaura cross-coupling reactions which take place selectivly at the C-B site. DFT calculations suggest the NaOtBu-catalyzed mixed 1,1-diboration of alkynes occurs through deprotonation of the terminal alkyne, stepwise addition of BpinBdan to the terminal carbon followed by protonation with tBuOH. Experimentally observed selective formation of (Z)-diborylalkenes is supported by our theoretical studies.},
  language  = {en}
}