Pd(II)-Catalyzed ortho-Arylation of Aryl Phosphates and Aryl Hydrogen Phosphates with Diaryliodonium Triflates

Abstract

Functionalized biaryl compounds were successfully synthesized using phosphates as the ortho-directing group in the Pd(II)/Pd(IV) catalytic cycle.

A comprehensive overview of directing groups applied in metal-catalysed C–H functionalisation chemistry

“…Targeting design of transformable/traceless P-containing DGs, several research groups focused on auxiliaries installed on an aromatic substrate via a heteroatom like O, or NH motif. Following this idea, enol phosphate DGs have been designed 1075 – 1078 and employed them in direct functionalisation of aromatics. In 2015 Loh expanded this reactivity by developing a catalytic system able to functionalise vinyl C–H bonds ( Scheme 172C ).…”

Diaryliodonium Salts in Organic Syntheses: A Useful Compound Class for Novel Arylation Strategies

“…al. 106 ) presented independently the innovative arylation of aryl phosphates (Scheme 60). The two reaction conditions marginally differ from each other, but these methods demonstrated their robust nature.…”

NCC Pincer Ni (II) Complexes Catalyzed Hydrophosphination of Nitroalkenes with Diphenylphosphine

“…[ 7 ] Moreover, phosphorus moieties could also be utilized as ortho‐directing groups to facilitate regioselective C‐H activation. [ 8 ] Recently, great effort has been made to prepare P‐containing compounds, [ 9 ] mainly including metal catalyzed cross‐coupling of prefunctionalized arenes, [ 10 ] C‐H functionalization of aromatics and other substrates, [ 11 ] and difunctionalization of alkenes [ 12 ] and alkynes [ 13 ] with various phosphorus precursors. Among these categories, metal‐catalyzed hydrophosphination of alkeneand alkynes represents an efficient methodology for the preparation of functionalized phosphorus products.…”