Lipshutz-type bis(amido)argentates for directed ortho argentation.

ABSTRACT: Bis(amido)argentate (TMP)₂Ag(CN)Li₂ (3, TMP-Ag-ate; TMP = 2,2,6,6-tetramethylpiperidido) was designed as a tool for chemoselective aromatic functionalization via unprecedented directed ortho argentation (DoAg). X-Ray crystallographic analysis showed that 3 takes a structure analogous to that of the corresponding Lipshutz cuprate. DoAg with this TMP-Ag-ate afforded multifunctional aromatics in high yields in processes that exhibited high chemoselectivity and compatibility with a wide range of functional groups. These included organometallics- and transition metal-susceptible substituents such as methyl ester, aldehyde, vinyl, iodo, (trifluoromethanesulfonyl)oxy and nitro groups. The arylargentates displayed good reactivity with

SUBMITTER: Tezuka N 

PROVIDER: S-EPMC8148356 | biostudies-literature | 2020 Jan

REPOSITORIES: biostudies-literature