“…Organoboronic acid derivatives are the most widely used class of building blocks for transition-metal-catalyzed Suzuki–Miyaura cross-coupling reactions . Conventional methods for the synthesis of organoboronic compounds typically start from the corresponding halide . However, in 2002, Ishiyama, Miyaura, and Hartwig developed an iridium-catalyzed C(sp 2 )–H borylation reaction of arenes that enabled the halide-free synthesis of arylboronic compounds with completely different regioselectivity to that generated by using halide-based methods .…”
Direct catalytic cyanation of organoboronic acids with cyanogen iodide has been achieved by using a copper-bipyridine catalyst system. The cyanation reaction is likely to occur through two catalytic cycles: copper(II)-catalyzed iodination of organoboronic acids and the following cyanidocopper(I)-mediated cyanation of organic iodides.
“…By comparison triarylphosphates react with alkyl and aryl Grignards in a similar manner to phosphoryl chloride. 32 Thiophosphoryl chloride reacts with aryl Grignards to form triarylphosphine oxides. 33 With low molecular weight primary alkyl Grignards, tetraalkylbiphosphine disulfides are generally formed instead.…”
Perfluoroalkyl Grignard reagents react with phosphoryl halides at -78 °C to room temperature to selectively produce bis(perfluoroalkyl)phosphonyl halides, which after aqueous work up, give bis(perfluoroalkyl)phosphinic acids in high overall yields. Reaction of perfluoroalkyl Grignards with phenylphosphonic dichloride gives high yields of bis(perfluoroalkyl)phenyl phosphine oxides which are readily hydrolysed to perfluoroalkyl(phenyl)phosphinic acids.
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