Nucleophilic aromatic substitution using Et3SiH/cat. t-Bu-P4 as a system for nucleophile activation

Masahiro Ueno; Misato Yonemoto; Masahiro Hashimoto; Andrew E H Wheatley; Hiroshi Naka; Yoshinori Kondo

doi:10.1039/b700140a

Nucleophilic aromatic substitution using Et3SiH/cat. t-Bu-P4 as a system for nucleophile activation

Chem Commun (Camb). 2007 Jun 14:(22):2264-6. doi: 10.1039/b700140a. Epub 2007 Feb 28.

Authors

Masahiro Ueno¹, Misato Yonemoto, Masahiro Hashimoto, Andrew E H Wheatley, Hiroshi Naka, Yoshinori Kondo

Affiliation

¹ Graduate School of Pharmaceutical Sciences, Tohoku University, Aramaki Aza Aoba 6-3, Sendai, 980-8578, Japan.

PMID: 17534511
DOI: 10.1039/b700140a

Abstract

A novel type of deprotonative arylation of nucleophiles was conducted using Et(3)SiH/cat. t-Bu-P4 and the powerful S(N)Ar reactions of aryl fluorides were accomplished using alcohols and malonates as nucleophiles.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alcohols / chemistry
Butanes / chemistry*
Catalysis
Hydrocarbons, Aromatic / chemistry*
Hydrocarbons, Fluorinated / chemistry*
Malonates / chemistry
Models, Chemical
Organophosphorus Compounds / chemistry*
Protons
Silanes / chemistry*

Substances

Alcohols
Butanes
Hydrocarbons, Aromatic
Hydrocarbons, Fluorinated
Malonates
Organophosphorus Compounds
Protons
Silanes
tert-butyl-P4
triethylsilane