Arylation of Diazocompounds Via Metal Free C-H Functionalization

The quest for an efficient methodology for the selective C-H functionalization of sp2 bond has long been considered as an attractive but challenging task in organic synthesis.1 In most reported methodologies, this transformation is either performed using expensive metals (i.e. rhodium, gold etc) or drastic reaction conditions.2 Only few representative examples are known so far for the arylation of diazocompounds via C-H functionalization. Herein, we are reporting a highly chemo- and regioselective substitution reaction via C-H functionalization between aryl compounds and α-aryl α-diazoacetates employing H2SO4.SiO2 as a green catalyst system. Similarly, we also tested chiral BrØnsted acid as catalysts to carry out this transformation in an asymmetric fashion. To our delight, we were able to isolate the α-arylation compound in moderate ee. Further studies are in progress to improve this ee. In short, this transformation offers simple reaction conditions, a wide substrate scope and high yields.