Synthesis of Siloxane Derivatives of Phenylboronic Acids of Different Structures

Abstract

The synthesis of a storage-stable organosilicon modifier with a dioxaborolane-protecting group is described. Its high reactivity and selective anti-Markovnikov addition in hydrosilylation reactions to afford siloxanes of various structures are shown. The possibility of deprotection of both the initial modifier and its siloxane derivatives under mild conditions using water in yields up to 96% is demonstrated. The existence of an equilibrium between the organosilicon derivatives of phenylboronic acids and their cyclic six-membered boroxines was confirmed by 1 H NMR spectroscopy and X-ray diffraction analysis data. The use of siloxane derivatives of phenylboronic acids in Suzuki−Miyaura and Chan−Lam cross-coupling reactions was studied. All synthesized compounds were characterized by NMR ( 1 H, 11 B, 13 C, and 29 Si), IR spectroscopy, and high-resolution mass spectrometry.