Suzuki–Miyaura Cross-Coupling of Potassium Trifluoro(N-methylheteroaryl)borates with Aryl and Heteroaryl Halides

Abstract

The synthesis of potassium trifluoro(N-methylheteroaryl)borates and their use in cross-coupling reactions with various aryl and heteroaryl halides to construct N-methyl heteroaryl-substituted aromatic and heteroaromatic compounds are reported.

31P NMR Evidence for Peroxide Intermediates in Lipid Emulsion Photooxidations: Phosphine Substituent Effects in Trapping

“…Phosphines 1 – 4 are usually reserved for use in organic and inorganic synthesis . Here, 1 and 2 , but not 3 and 4 , were shown to be efficient trapping agents for peroxides in postphotooxidation/photoreactions of Intralipid.…”

“…sSPhos is unique; it contains two cyclohexane rings and an arylsulfonate ion. Bulky electron‐rich phosphines such as sSPhos 1 are ligands for Suzuki–Miyaura cross‐coupling reactions in the field of organic synthesis, facilitating C–C, C–N and C–O bond formations . Organic solvent soluble phosphines are highly oxophilic and trap oxygen from peroxide sources .…”

Palladium-Catalyzed C–N Cross-Coupling of NH-Heteroarenes and Quaternary Ammonium Salts via C–N Bond Cleavage

“…1 1-(4-Methoxybenzyl)-1H-indole (4m). 46 Following the general procedure, 4m was obtained as a white oil with petroleum ether/ethyl acetate (20/1) used as the eluent in 80% yield (188.9 mg). 1 (2-Methoxybenzyl)-1H-indole (4n).…”

Improving Transformations Through Organotrifluoroborates

“…This method was later extended to the coupling of trifluoro(N-methylheteroaryl) borates [25], secondary ammoniomethyltrifluoroborates [26], and sulfonamidomethyltrifluoroborates [27] by using slightly modified reaction conditions. These methods allow access to a variety of highly valued aminomethylated arene cores.…”