Regioselectivity of the borylation of alkanes and arenes

2011/01/01 by John F. Hartwig · 1 citation
Chemistry · #Catalytic C–H Functionalization Methods #Organoboron and organosilicon chemistry #Catalytic Cross-Coupling Reactions

paper · doi:10.1039/c0cs00156b

openalex publication_date 2011/01/01 · openalex created_date 2016/06/24 · openalex updated_date 2026/07/30

Abstract

The borylation of alkanes and arenes has become some of the most practical C-H bond functionalization chemistry. Most striking is the high regioselectivity of these reactions. Rhodium and ruthenium complexes catalyze with exquisite selectivity the borylation of methyl C-H bonds over methylene or methine C-H bonds. Iridium complexes catalyze, with high steric control, the borylation of one aromatic C-H bond over another. In contrast, iridium-catalyzed borylation of heteroaromatic C-H bonds is more controlled by electronic effects. Detailed information on these selectivities and mechanistic information on the origins of this regioselectivity will be described in this critical review (95 references).

Citations

• C−H Activation for the Construction of C−B Bonds
• Activation of saturated hydrocarbons by metal complexes in solution
• Catalytic Carbene Insertion into C−H Bonds
• Iridium PCP pincer complexes: highly active and robust catalysts for novel homogeneous aliphatic dehydrogenations
• Activation of C−H Bonds by Metal Complexes
• Metal-Catalyzed Reactions of Organoboronic Acids and Esters

Cited by

• Iridium [wikipedia]