TY  - JOUR
A1  - Liu, Zhiqiang
A1  - Kole, Goutam Kumar
A1  - Budiman, Yudha P.
A1  - Tian, Ya-Ming
A1  - Friedrich, Alexandra
A1  - Luo, Xiaoling
A1  - Westcott, Stephen A.
A1  - Radius, Udo
A1  - Marder, Todd B.
T1  - Transition metal catalyst-free, base-promoted 1,2-additions of polyfluorophenylboronates to aldehydes and ketones
JF  - Angewandte Chemie International Edition
N2  - A novel protocol for the transition metal-free 1,2-addition of polyfluoroaryl boronate esters to aldehydes and ketones is reported, which provides secondary alcohols, tertiary alcohols, and ketones. Control experiments and DFT calculations indicate that both the ortho-F substituents on the polyfluorophenyl boronates and the counterion K\(^+\) in the carbonate base are critical. The distinguishing features of this procedure include the employment of commercially available starting materials and the broad scope of the reaction with a wide variety of carbonyl compounds giving moderate to excellent yields. Intriguing structural features involving O−H⋅⋅⋅O and O−H⋅⋅⋅N hydrogen bonding, as well as arene-perfluoroarene interactions, in this series of racemic polyfluoroaryl carbinols have also been addressed.
KW  - inorganic chemistry
KW  - transition metal-free
KW  - alcohol
KW  - 1,2-additionreaction
KW  - boronateesters
KW  - fluoroarene
Y1  - 2021
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-256487
VL  - 60
IS  - 30
ER  - 
TY  - JOUR
A1  - Ivanova, Svetlana
A1  - Köster, Eva
A1  - Holstein, Julian J.
A1  - Keller, Niklas
A1  - Clever, Guido H.
A1  - Bein, Thomas
A1  - Beuerle, Florian
T1  - Isoreticular crystallization of highly porous cubic covalent organic cage compounds
JF  - Angewandte Chemie International Edition
N2  - Modular frameworks featuring well-defined pore structures in microscale domains establish tailor-made porous materials. For open molecular solids however, maintaining long-range order after desolvation is inherently challenging, since packing is usually governed by only a few supramolecular interactions. Here we report on two series of nanocubes obtained by co-condensation of two different hexahydroxy tribenzotriquinacenes (TBTQs) and benzene-1,4-diboronic acids (BDBAs) with varying linear alkyl chains in 2,5-position. n-Butyl groups at the apical position of the TBTQ vertices yielded soluble model compounds, which were analyzed by mass spectrometry and NMR spectroscopy. In contrast, methyl-substituted cages spontaneously crystallized as isostructural and highly porous solids with BET surface areas and pore volumes of up to 3426 m\(^2\) g\(^{-1}\) and 1.84 cm\(^3\) g\(^{-1}\). Single crystal X-ray diffraction and sorption measurements revealed an intricate cubic arrangement of alternating micro- and mesopores in the range of 0.97–2.2 nm that are fine-tuned by the alkyl substituents at the BDBA linker.
KW  - organic chemistry
KW  - structure elucidation
KW  - boronateesters
KW  - cage compounds
KW  - dynamic covalent chemistry
KW  - porousmaterials
Y1  - 2021
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-256462
VL  - 60
IS  - 32
ER  -