TY  - JOUR
A1  - Liu, Zhiqiang
A1  - Budiman, Yudha P.
A1  - Tian, Ya‐Ming
A1  - Friedrich, Alexandra
A1  - Huang, Mingming
A1  - Westcott, Stephen A.
A1  - Radius, Udo
A1  - Marder, Todd B.
T1  - Copper‐Catalyzed Oxidative Cross‐Coupling of Electron‐Deficient Polyfluorophenylboronate Esters with Terminal Alkynes
JF  - Chemistry – A European Journal
N2  - 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.
KW  - boronate esters
KW  - coupling reactions
KW  - fluorine
KW  - fluoroarenes
KW  - Sonogashira reaction
Y1  - 2020
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-224362
VL  - 26
IS  - 71
SP  - 17267
EP  - 17274
ER  - 
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  -