@phdthesis{Huang2022,
  author    = {Huang, Mingming},
  title     = {C-S Bond Borylation and Diborylation of Alkyl Halides, Tosylates, and Alcohols},
  doi       = {10.25972/OPUS-25718},
  url       = {http://nbn-resolving.de/urn:nbn:de:bvb:20-opus-257186},
  school      = {Universit{\"a}t W{\"u}rzburg},
  year      = {2022},
  abstract  = {Alkylboronates play an important role in synthetic chemistry, materials science and drug discovery. They are easy to handle due to their good air and moisture stability, and can be readily employed to form carbon-carbon and carbon-heteroatom bonds and can be converted to various functional groups under mild reaction conditions. Compared with conventional groups, such as aryl (pseudo)halides or alcohols, organosulfur compounds represent an alternative and complimentary substitute in coupling reactions. The construction of C-B bond from C-SO bond of aryl sulfoxide is presented in Chapter 2. The selective cleavage of either alkyl(C)-sulfonyl or aryl(C)-sulfonyl bonds of an aryl alkyl sulfone via Cu-free or Cu-mediated processes generates the corresponding boronate esters, which are presented in Chapter 3 and Chapter 4. 1,2-Bis(boronate esters) are emerging as important synthetic intermediates for preparing 1,2-difunctional compounds. In addition, the boryl moieties in different environments in a 1,2-bis(boronate ester) can be differentiated and converted selectively, allowing the synthesis of a wide variety of complex molecules. A direct and selective diboration of C-X and C-O bonds for the preparation of 1,2-bis(boronate esters) is presented in Chapter 5.},
  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}
}
@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{HuangWuKrebsetal.2021,
  author    = {Huang, Mingming and Wu, Zhu and Krebs, Johannes and Friedrich, Alexandra and Luo, Xiaoling and Westcott, Stephen A. and Radius, Udo and Marder, Todd B.},
  title     = {Ni-Catalyzed Borylation of Aryl Sulfoxides},
  series = {Chemistry—A European Journal},
  volume    = {27},
  journal   = {Chemistry—A European Journal},
  number    = {31},
  doi       = {10.1002/chem.202100342},
  url       = {http://nbn-resolving.de/urn:nbn:de:bvb:20-opus-256778},
  pages     = {8149-8158},
  year      = {2021},
  abstract  = {A nickel/N-heterocyclic carbene (NHC) catalytic system has been developed for the borylation of aryl sulfoxides with B\(_{2}\)(neop)\(_{2}\) (neop=neopentyl glycolato). A wide range of aryl sulfoxides with different electronic and steric properties were converted into the corresponding arylboronic esters in good yields. The regioselective borylation of unsymmetric diaryl sulfoxides was also feasible leading to borylation of the sterically less encumbered aryl substituent. Competition experiments demonstrated that an electron-deficient aryl moiety reacts preferentially. The origin of the selectivity in the Ni-catalyzed borylation of electronically biased unsymmetrical diaryl sulfoxide lies in the oxidative addition step of the catalytic cycle, as oxidative addition of methoxyphenyl 4-(trifluoromethyl)phenyl sulfoxide to the Ni(0) complex occurs selectively to give the structurally characterized complex trans-[Ni(ICy)\(_{2}\)(4-CF\(_{3}\)-C\(_{6}\)H\(_{4}\)){(SO)-4-MeO-C\(_{6}\)H\(_{4}\)}] 4. For complex 5, the isomer trans-[Ni(ICy)\(_{2}\)(C\(_{6}\)H\(_{5}\))(OSC\(_{6}\)H\(_{5}\))] 5-I was structurally characterized in which the phenyl sulfinyl ligand is bound via the oxygen atom to nickel. In solution, the complex trans-[Ni(ICy)\(_{2}\)(C\(_{6}\)H\(_{5}\))(OSC\(_{6}\)H\(_{5}\))] 5-I is in equilibrium with the S-bonded isomer trans-[Ni(ICy)\(_{2}\)(C\(_{6}\)H\(_{5}\))(SOC\(_{6}\)H\(_{5}\))] 5, as shown by NMR spectroscopy. DFT calculations reveal that these isomers are separated by a mere 0.3 kJ/mol (M06/def2-TZVP-level of theory) and connected via a transition state trans-[Ni(ICy)\(_{2}\)(C\(_{6}\)H\(_{5}\))(η\(^{2}\)-{SO}-C\(_{6}\)H\(_{5}\))], which lies only 10.8 kcal/mol above 5.},
  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}
}