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

This review discusses recent advances in the chemistry of saturated boronic acids, boronates, and trifluoroborates. Applications of the title compounds in the design of boron-containing drugs are surveyed, with special emphasis on alpha-amino boronic derivatives. A general overview of saturated boronic compounds as 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 the art in the synthesis of saturated boronic acids, boronates, and trifluoroborates is made, with a brief mention of the classical methods (transmetallation of organolithium/magnesium reagents with boron species, anti-Markovnikov hydroboration of alkenes, and the modification of alkenyl boron compounds) and a special focus on 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).

Automated summary

This review discusses recent advances in the chemistry of saturated boronic acids, boronates, and trifluoroborates, focusing on their applications in drug design and bond construction. It provides an overview of classical methods and recent methodologies in the synthesis of these compounds.