Saturated Boronic Acids, Boronates, and Trifluoroborates: An Update on Their Synthetic and Medicinal Chemistry

Abstract

A review with 349 references discussing recent advances in the chemistry of saturated boronic acids, boronates, and trifluoroborates. Applications of the title compounds in design of boron-containing drugs are surveyed, with special emphasis on a-amino boronic derivatives. A general overview of saturated boronic compounds as the modern tools to construct C( sp 3 )–C and C( sp 3 ) – heteroatom bonds is given, including recent developments in the Suzuki – Miyaura and Chan – Lam cross-couplings, single-electron transfer processes including metallo- and organocatalytic photoredox reactions, and transformations of boron ‘ate’ complexes. Finally, an attempt to summarize the current state-of-art in the synthesis of saturated boronic acids, boronates, and trifluoroborates is made, with brief mentioning of the ‘classical’ methods (transmetallation of organolithium/magnesium reagents with boron species, anti-Markovnikov hydroboration of alkenes, and modification of alkenyl boron compounds) and special focus on the recent methodologies (boronation of alkyl (pseudo)halides, derivatives of carboxylic acids, alcohols, and primary amines, boronative C–H activation, novel approaches to alkene hydro­boration, and 1,2-metallate-type rearrangements).