ChanLamkopplingar

ChanLamkopplingar, also known as Chan-Lam coupling reactions, are a class of organic reactions used to form carbon-heteroatom bonds. Specifically, these reactions facilitate the formation of carbon-nitrogen, carbon-oxygen, and carbon-sulfur bonds. The reaction typically involves the coupling of an organoboron compound (boronic acid or boronate ester) with a heteroatom nucleophile, such as an amine, alcohol, or thiol, in the presence of a copper catalyst and an oxidant.

The general mechanism of a Chan-Lam coupling involves the oxidation of copper(I) to copper(II), which then undergoes transmetalation with the organoboron species. The resulting organocopper intermediate then reacts with the heteroatom nucleophile, followed by reductive elimination to form the desired carbon-heteroatom bond and regenerate the copper catalyst. Various oxidants, such as oxygen or peroxides, can be employed to facilitate the catalytic cycle.

These coupling reactions offer several advantages, including mild reaction conditions, tolerance to a wide range of functional groups, and the use of readily available and relatively stable organoboron reagents. They have become a valuable tool in synthetic organic chemistry for the construction of complex molecules, particularly in pharmaceutical and materials science research. The development of various ligand systems has further expanded the scope and efficiency of Chan-Lam coupling reactions, allowing for the synthesis of diverse and challenging molecular architectures.