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

Bis(amido)argentate (TMP) Ag(CN)Li ( , TMP-Ag-ate; TMP = 2,2,6,6-tetramethylpiperidido) was designed as a tool for chemoselective aromatic functionalization unprecedented directed argentation (D Ag). X-Ray crystallographic analysis showed that takes a structure analogous to that of the corresponding...

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Bibliographic Details
Published in:Chemical science (Cambridge) 2020-01, Vol.11 (7), p.1855-1861
Main Authors: Tezuka, Noriyuki, Hirano, Keiichi, Peel, Andrew J, Wheatley, Andrew E H, Miyamoto, Kazunori, Uchiyama, Masanobu
Format: Article
Language:English
Subjects:
Aldehydes
Chemical reactions
Chemistry
Crystallography
Functional groups
Organometallic compounds
Transition metals
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Summary:Bis(amido)argentate (TMP) Ag(CN)Li ( , TMP-Ag-ate; TMP = 2,2,6,6-tetramethylpiperidido) was designed as a tool for chemoselective aromatic functionalization unprecedented directed argentation (D Ag). X-Ray crystallographic analysis showed that takes a structure analogous to that of the corresponding Lipshutz cuprate. D Ag 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 various electrophiles. Chalcogen (S, Se, and Te) installation and azo coupling reactions also proceeded efficiently.
ISSN:2041-6520
2041-6539
DOI:10.1039/c9sc06060j