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  - 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  - Budiman, Yudha P.
A1  - Lorenzen, Sabine
A1  - Liu, Zhiqiang
A1  - Radius, Udo
A1  - Marder, Todd B.
T1  - Base‐Free Pd‐Catalyzed C−Cl Borylation of Fluorinated Aryl Chlorides
JF  - Chemistry – A European Journal
N2  - Catalytic C−X borylation of aryl halides containing two ortho‐fluorines has been found to be challenging, as most previous methods require stoichiometric amounts of base and the polyfluorinated aryl boronates suffer from protodeboronation, which is accelerated by ortho‐fluorine substituents. Herein, we report that a combination of Pd(dba)2 (dba=dibenzylideneacetone) with SPhos (2‐dicyclohexylphosphino‐2’,6’‐dimethoxybiphenyl) as a ligand is efficient to catalyze the C‐Cl borylation of aryl chlorides containing two ortho‐fluorine substituents. This method, conducted under base‐free conditions, is compatible with the resulting di‐ortho‐fluorinated aryl boronate products which are sensitive to base.
KW  - boronate ester
KW  - borylation
KW  - cross-coupling
KW  - fluoroarene
KW  - palladium-catalyzed
Y1  - 2021
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-225687
VL  - 27
IS  - 11
SP  - 3869
EP  - 3874
ER  - 
TY  - JOUR
A1  - Budiman, Yudha P.
A1  - Westcott, Stephen A.
A1  - Radius, Udo
A1  - Marder, Todd B.
T1  - Fluorinated Aryl Boronates as Building Blocks in Organic Synthesis
JF  - Advanced Synthesis & Catalysis
N2  - Organoboron compounds are well known building blocks for many organic reactions. However, under basic conditions, polyfluorinated aryl boronic acid derivatives suffer from instability issues that are accelerated in compounds containing an ortho‐fluorine group, which result in the formation of the corresponding protodeboronation products. Therefore, a considerable amount of research has focused on novel methodologies to synthesize these valuable compounds while avoiding the protodeboronation issue. This review summarizes the latest developments in the synthesis of fluorinated aryl boronic acid derivatives and their applications in cross‐coupling reactions and other transformations.

image
KW  - homogeneous catalysis
KW  - boron reagents
KW  - boronates
KW  - fluorine
KW  - fluoroarene
Y1  - 2021
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-225908
VL  - 363
IS  - 9
SP  - 2224
EP  - 2255
ER  -