Photoinduced Borylation for the Synthesis of Organoboron Compounds

• Published in: Chemical reviews Vol. 121; no. 7; pp. 3561 - 3597
• Main Authors: Tian, Ya-Ming, Guo, Xiao-Ning, Braunschweig, Holger, Radius, Udo, Marder, Todd B
• Format: Journal Article
• Language: English
• Published: United States American Chemical Society 14.04.2021
• Subjects: Alcohols; Alkanes; Amines; Aromatic compounds; Carboxylic acids; Catalysis; Coordination compounds; Electron transfer; Energy transfer; Esters; Halides; Metals; Organoboron compounds; Photochemicals; Reaction mechanisms; Single electrons; Transition metals
• ISSN: 0009-2665; 1520-6890
• DOI: 10.1021/acs.chemrev.0c01236

Organoboron compounds have important synthetic value and can be applied in numerous transformations. The development of practical and convenient ways to synthesize boronate esters has thus attracted significant interest. Photoinduced borylations originated from stoichiometric reactions of alkanes and arenes with well-defined metal-boryl complexes. Now, photoredox-initiated borylations, catalyzed by either transition metal or organic photocatalysts, and photochemical borylations with high efficiency have become a burgeoning area of research. In this Focus Review, we summarize research on photoinduced borylations, especially emphasizing recent developments and trends. This includes the photoinduced borylation of arenes, alkanes, aryl/alkyl halides, activated carboxylic acids, amines, alcohols, and so on based on transition metal catalysis, metal-free organocatalysis, and direct photochemical activation. We focus on reaction mechanisms involving single-electron transfer, triplet-energy transfer, and other radical processes.