A Review on the Latest Progress of Chan‐Lam Coupling Reaction

Abstract

Chan‐Lam reactions hold promise as one of the most efficient synthetic methods to construct various carbon‐heteroatom or carbon‐carbon bonds. Recently, a series of Chan‐Lam reactions were developed to boost organic synthesis. Herein, we summarized the latest research and progress of Chan‐Lam coupling to illustrate its synthetic value.magnified image

CH-Diazomethane Sulfonamides Generated in Situ for Intramolecular [3+2] Cycloaddition of Alkynes: An Entry into Novel Pyrazole-Fused Five-Membered Sultams

“…Copper-catalyzed C-N coupling involving arylboronic acids, a procedure known as the Chan-Evans-Lam reaction, has been widely recognized as a remarkably efficient and often regioselective method for the N-arylation of various nitrogen heterocycles, including pyrazoles. 21 To our delight, sultam-fused pyrazoles 14c,d were indeed efficiently (albeit somewhat slowly) N-arylated with boronic acids at ambient temperature. Notably, derivatives 17a,b were formed from compound 14c with complete diastereoselectivity.…”

Photocatalysis in Dual Catalysis Systems for Carbon‐Nitrogen Bond Formation

“…Many pharmaceuticals, agrochemicals industries and even material sciences require nitrogen‐containing organic compounds. Therefore, the functionalization of C−X bonds with Buchwald‐Hartwig and Ullmann Cross coupling reactions are of paramount importance [5b–d] . These conventional methods usually face limitations such as elongated reaction time, elevated temperatures and expensive catalysts with complex ligand systems [5] .…”

Cu(OAc)2‐porphyrins as an efficient catalytic system for base‐free, nature mimicking Chan–Lam coupling in water

“…[ 29,31–33 ] Common strategies to access the arylated amines include (i) the activation of aryl halide/ethers/esters toward aromatic nucleophilic substitution (S N Ar) using amines, [ 34–36 ] (ii) Ullmann/Buchwald–Hartwig coupling of aryl halides and amines, [ 37–40 ] and (iii) Chan–Lam coupling of arylamines and arylboronic acids. [ 41–43 ] The first two strategies often required elevated temperature, stoichiometric ratios of catalysts and expensive solvents, and bases. [ 34–40 ] On the other hand, the Chan–Lam coupling enables the preparation of arylamines at mild conditions using highly reactive substrates such as organoboronic acids and amines.…”