Issue 7, 2020
From the journal:

Chemical Science

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

Noriyuki Tezuka, ORCID logo *ab   Keiichi Hirano, ORCID logo *ab   Andrew J. Peel, ORCID logo c   Andrew E. H. Wheatley, ORCID logo c   Kazunori Miyamoto ORCID logo ab  and  Masanobu Uchiyama ORCID logo *abd  

* Corresponding authors

a Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan
E-mail: tezuka-noriyuki@g.ecc.u-tokyo.ac.jp, k1hirano@mol.f.u-tokyo.ac.jp, uchiyama@mol.f.u-tokyo.ac.jp

b Cluster of Pioneering Research (CPR), Advanced Elements Chemistry Laboratory, RIKEN, 2-1 Hirosawa, Wako-shi, Saitama 351-0198, Japan

c Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, UK

d Research Initiative for Supra-Materials (RISM), Shinshu University, 3-15-1 Tokida, Ueda, Nagano 386-8567, Japan

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 various electrophiles. Chalcogen (S, Se, and Te) installation and azo coupling reactions also proceeded efficiently.

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

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Article information

DOI
https://doi.org/10.1039/C9SC06060J
Article type
Edge Article
Submitted
30 Nov 2019
Accepted
02 Jan 2020
First published
07 Jan 2020
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2020,11, 1855-1861

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

N. Tezuka, K. Hirano, A. J. Peel, A. E. H. Wheatley, K. Miyamoto and M. Uchiyama, Chem. Sci., 2020, 11, 1855 DOI: 10.1039/C9SC06060J

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