An efficient method for the chemoselective and desulfurative chan. A naturally encoded dipeptide handle for bioorthogonal. Copperii fluoride a new efficient promoter of chanlam. Synthetic applications and methodology development of chan. In addition to the synthetic complementarity, this approach is supported in a practical sense by the impressive catalog of. The chan evans lam reaction is a valuable cn bond forming process. Lam cross coupling is unique reaction between an organoboron compound and an amine under oxidative conditions scheme 1a. Coupling chemistry of high oxidaon state cu and pd robert j comito macmillan group meeng may 25, 2011 n n pdiv oac. The chan lam evans coupling is the copperii acetate promoted reaction of phenols and boronic acids producing diaryl ethers. Chanevanslam amination of boronic acid pinacol bpin. Substrate selectivity and reactivity in chan lam cross. Substrates include phenols, amines, anilines, amides, imides, ureas, carbamates, and sulfonamides. This reaction allows aryl carbonheteroatom bond formation via an oxidative coupling of boronic acids, stannanes or siloxanes with nh or oh containing compounds in air. Herein, we report effective reaction conditions for the chan evans lam amination of aryl bpin with alkyl and aryl amines.
In this paper a modification of the original reaction is reported. The chanlam coupling reaction also known as the chan evans lam coupling is a cross coupling reaction between an aryl boronic acid and an alcohol or an amine to form the corresponding secondary aryl amines or aryl ethers, respectively. Chanlam coupling reaction of sulfamoyl azides with. However, aryl boronic acid pinacol bpin ester reagents can be difficult coupling partners that often deliver low yields, in particular in reactions with aryl amines. The mild condition of this reaction is an advantage over buchwaldhartwigs pdcatalyzed cross coupling. The chanlam coupling is catalyzed by copper complexes. Chan lam coupling is one of the most popular and easy methods to perform arylation of amines narylations. Functionalization of silica surface using chanlam coupling. Chan lam coupling reaction of sulfamoyl azides with arylboronic acids for synthesis of unsymmetrical narylsulfamides sukyoung won,a seoeun kim,a yongju kwon,a inji shin,bc jungyeob hamd and wonsuk kim a an e. By modulating the amount of the catalyst cuoac 2 h 2 o, a. An improved piiipv ocatalyzed reductive cn coupling of.
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