Tandem Arylation/[1,2]-Wittig Rearrangement of Pyridylmethyl Ethers

Transition-metal-catalyzed cross-coupling reactions are among the most useful and versatile methods in the field of synthetic organic chemistry, especially to form key carbon–carbon bonds. A long-standing goal of this chemistry is to develop efficient methods to provide valuable compounds found in natural products and bioactive small molecules. While classical approaches use prefunctionalized nucleophiles, recent trends in the area of the cross-coupling chemistry involve direct functionalization of simple starting pronucleophiles. Recently, Professor Patrick J. Walsh’s group at the University of Pennsylvania (USA) has been interested in the functionalization of weakly acidic C(sp3)–H bonds through a deprotonative cross-coupling process (DCCP), wherein a weakly acidic C–H of the substrate is deprotonated by a base and functionalized in the presence of a transition-metal catalyst. 

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