@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}
}
@article{LiuMingFriedrichetal.2020,
  author    = {Liu, Xiaocui and Ming, Wenbo and Friedrich, Alexandra and Marder, Todd B.},
  title     = {Kupfer-katalysierte Triborierung terminaler Alkine mit B2pin2: Effiziente Synthese von 1,1,2-Triborylalkenen},
  series = {Angewandte Chemie},
  volume    = {132},
  journal   = {Angewandte Chemie},
  number    = {1},
  doi       = {10.1002/ange.201908466},
  url       = {http://nbn-resolving.de/urn:nbn:de:bvb:20-opus-219699},
  pages     = {311-316},
  year      = {2020},
  abstract  = {Wir berichten {\"u}ber die katalytische Triborierung terminaler Alkine mit B\(_2\)pin\(_2\) (Bis-(pinakolato)-dibor) unter Verwendung von einfach zug{\"a}nglichem Cu(OAc)\(_2\) und P\(^n\)Bu\(_3\). Verschiedene 1,1,2-Triborylalkene, eine Verbindungsklasse mit potentieller Funktion als Matrix-Metallo-Proteinase(MMP-2)-Inhibitor, werden direkt in m{\"a}ßigen bis guten Ausbeuten erhalten. Das Verfahren zeichnet sich durch milde Reaktionsbedingungen, ein breites Substratspektrum und eine gute Vertr{\"a}glichkeit gegen{\"u}ber funktionellen Gruppen aus. Diese Cu-katalysierte Reaktion kann im Gramm-Maßstab durchgef{\"u}hrt werden und liefert die entsprechenden 1,1,2-Triborylalkene in m{\"a}ßigen Ausbeuten. Die Verwendung solcher Verbindungen wird anhand weiterer Transformationen der C-B-Bindungen zur Darstellung eines geminalen Dihalogenborylalkens (F, Cl, Br), eines Monohalogendiborylalkens (Cl, Br) und eines trans-Diaryldiborylalkens demonstriert, welche bedeutende Synthesebausteine darstellen und bisher nur schwer zug{\"a}nglich waren.},
  language  = {de}
}
@phdthesis{Liu2020,
  author    = {Liu, Xiaocui},
  title     = {Catalytic Triboration and Diboration of Terminal Alkynes},
  doi       = {10.25972/OPUS-19253},
  url       = {http://nbn-resolving.de/urn:nbn:de:bvb:20-opus-192537},
  school      = {Universit{\"a}t W{\"u}rzburg},
  year      = {2020},
  abstract  = {Chapter two reports the catalytic triboration of terminal alkynes with B2pin2 using readily available Cu(OAc)2 and PnBu3. Various 1,1,2-triborylalkenes, a class of compounds which have been demonstrated to be potential Matrix Metalloproteinase-2 (MMP-2) inhibitors, are obtained directly in moderate to good yields. The process features mild reaction conditions, broad substrate scope, and good functional group tolerance were observed. This Cu-catalyzed reaction can be conducted on a gram scale to produce the corresponding 1,1,2-triborylalkenes in modest yields. The utility of these products is demonstrated by further transformation of the C-B bonds to prepare gem-dihaloborylalkenes (F, Cl, Br), monohalodiborylalkenes (Cl, Br), and trans-diaryldiborylalkenes, which serve as important synthons and have previously been challenging to prepare. A convenient and efficient one step synthesis of 1,1,1-triborylalkanes was achieved via sequential dehydrogenative borylation and double hydroboration of terminal alkynes with HBpin (HBpin = pinacolborane) catalyzed by inexpensive and readily available Cu(OAc)2. This protocol proceeded under mild conditions, furnishing 1,1,1-tris(boronates) with wide substrate scope, excellent selectivity and good functional group tolerance, and is applicable to gram-scale synthesis without loss of yield. The 1,1,1-triborylalkanes can be used in the preparation of α-vinylboronates and borylated cyclic compounds, which are valuable but previously rare compounds. Different alkyl groups can be introduced stepwise via base-mediated deborylative alkylation to produce racemic tertiary alkyl boronates, which can be readily transformed into useful tertiary alcohols. Chapter 4 reported a NaOtBu-catalyzed mixed 1,1-diboration of terminal alkynes with an unsymmetrical diboron reagent BpinBdan. This Br{\o}nsted base-catalyzed reaction proceeds in a regio- and stereoselective fashion affording 1,1-diborylalkenes with two different boryl moieties in moderate to high yields, and is applicable to gram-scale synthesis without loss of yield or selectivity. Hydrogen bonding between the Bdan group and tBuOH is proposed to be responsible for the observed stereoselectivity. The mixed 1,1-diborylalkenes can be utilized in stereoselective Suzuki-Miyaura cross-coupling reactions.},
  subject      = {Borylierung},
  language  = {en}
}
@article{LiuMingFriedrichetal.2020,
  author    = {Liu, Xiaocui and Ming, Wenbo and Friedrich, Alexandra and Kerner, Florian and Marder, Todd B.},
  title     = {Copper-Catalyzed Triboration of Terminal Alkynes Using B\(_2\)pin\(_2\): Efficient Synthesis of 1,1,2-Triborylalkenes},
  series = {Angewandte Chemie International Edition},
  volume    = {59},
  journal   = {Angewandte Chemie International Edition},
  number    = {1},
  doi       = {10.1002/anie.201908466},
  url       = {http://nbn-resolving.de/urn:nbn:de:bvb:20-opus-206694},
  pages     = {304-309},
  year      = {2020},
  abstract  = {We report herein the catalytic triboration of terminal alkynes with B\(_2\)pin\(_2\) (bis(pinacolato)diboron) using readily available Cu(OAc)\(_2\) and P\(^n\)Bu\(_3\). Various 1,1,2-triborylalkenes, a class of compounds that have been demonstrated to be potential matrix metalloproteinase (MMP-2) inhibitors, were obtained directly in moderate to good yields. The process features mild reaction conditions, a broad substrate scope, and good functional group tolerance. This copper-catalyzed reaction can be conducted on a gram scale to produce the corresponding 1,1,2-triborylalkenes in modest yields. The utility of these products was demonstrated by further transformations of the C-B bonds to prepare gem -dihaloborylalkenes (F, Cl, Br), monohaloborylalkenes (Cl, Br), and trans -diaryldiborylalkenes, which serve as important synthons and have previously been challenging to prepare.},
  language  = {en}
}