Bulky Diamine Ligand Promotes Cross‐Coupling of Difluoroalkyl Bromides by Iron Catalysis

Abstract

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A Bright Deep-Red AIEgen with Locked Noncoplanar Conformation for Lipid Droplet-Specific Imaging

“…Therefore, the development of superior LDs probe and study the physiological behavior of LDs become highly significant in biomedical research. 59,60 TPABSM is a superior liposoluble luminescent molecule, and the fluorine is a commonly used atom to improve the lipophilicity of drug molecules, 61,62 which thus inspired us to explore the possibility of TPABSM as a dye for LDs imaging. Before the experiment, we first calculated the logP (n-octanol/water partition coefficient) value of TPABSM because pioneering work has reported that organic dyes for lipid droplets staining usually exhibited logP value larger than 5 predicted by using QSAR (quantitative structure activity relations) models.…”

Nickel‐Catalyzed 1,1‐Difluoroethylation of (Hetero)aryl Halides with 1,1‐Difluoroethyl Chloride (CH3CF2Cl)

“…Hu and co‐workers reported a copper‐mediated aromatic 1,1‐difluoroethylation with Me 3 SiCF 2 CH 3 via “CuCF 2 CH 3 ” . Yamakawa and Zhang groups reported cobalt‐ and iron‐catalyzed difluoroalkylation of aryl Grignard reagents with CH 3 CF 2 Br, respectively (Scheme B).…”

Cu-Catalyzed Arylation of Bromo-Difluoro-Acetamides by Aryl Boronic Acids, Aryl Trialkoxysilanes and Dimethyl-Aryl-Sulfonium Salts: New Entries to Aromatic Amides

“…We set out to explore 2-bromo-2,2-difluoroacetamides 1 in coupling reactions with aryl boronic acids 2 and (aryl)trialkoxysilanes 3 arylation agents as donors of aryl or heteroaryl substituents ( Scheme 1 a). We hypothesized ( Scheme 1 b) that using transition-metal-assisted catalysis, a 2-bromo-2,2-difluoroacetamide unit could undergo an oxidative addition on an appropriately tuned by ligands metal nuclei, forming an organometallic intermediate (structure 6 ) [ 35 , 36 , 37 ], followed by a rearrangement possibly via a CF 2 -carbene complex 7 , which undergoes loss of difluorocarben and simultaneous exchange of Br versus F giving rise to an organometallic (intermediate 8 ) capable of undergoing reaction with aryl boronic acids or aryl trialkoxysilanes to deliver a new intermediate ( 9 ), which after the reductive elimination would result in the formation of a new C-C bond to yield the desired aryl amide ( 5 ). An alternative mechanistic pathway could be via copper-intermediate 11 ( Scheme 1 c), as a result of the reaction between a fluorinated transition-metal catalyst and an aryl boronic acid (or aryl trialkoxysilane).…”