Nucleophilic Aromatic Substitution at Benzene with Powerful Strontium Hydride and Alkyl Complexes

Angewandte Chemie
Bastian RöschSjoerd Harder

Abstract

Key to the isolation of the first alkyl strontium complex was the synthesis of a strontium hydride complex that is stable towards ligand exchange reactions. This goal was achieved by using the super bulky β-diketiminate ligand DIPeP BDI (CH[C(Me)N-DIPeP]2 , DIPeP=2,6-diisopentylphenyl). Reaction of DIPeP BDI-H with Sr[N(SiMe3 )2 ]2 gave (DIPeP BDI)SrN(SiMe3 )2 , which was converted with PhSiH3 into [(DIPeP BDI)SrH]2 . Dissolved in C6 D6 , the strontium hydride complex is stable up to 70 °C. At 60 °C, H-D isotope exchange gave full conversion into [(DIPeP BDI)SrD]2 and C6 D5 H. Since H-D exchange with D2 is facile, the strontium hydride complex served as a catalyst for the deuteration of C6 H6 by D2 . Reaction of [(DIPeP BDI)SrH]2 with ethylene gave [(DIPeP BDI)SrEt]2 . The high reactivity of this alkyl strontium complex is demonstrated by facile ethylene polymerization and nucleophilic aromatic substitution with C6 D6 , giving alkylated aromatic products and [(DIPeP BDI)SrD]2 .

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Citations

Apr 11, 2019·Chemistry : a European Journal·Michael Mauksch, Svetlana B Tsogoeva
Aug 30, 2019·Angewandte Chemie·Steffen BrandSjoerd Harder
Oct 12, 2019·Chemical Communications : Chem Comm·Louis J MorrisNasir A Rajabi
Nov 30, 2019·Dalton Transactions : an International Journal of Inorganic Chemistry·Xianghui ShiJianhua Cheng
Nov 19, 2019·Angewandte Chemie·Michael Stephen HillEmma Richards
Jun 10, 2020·Dalton Transactions : an International Journal of Inorganic Chemistry·Zhizhou LiuJianhua Cheng
Jul 14, 2020·Chemical Communications : Chem Comm·Johannes MartinSjoerd Harder
Aug 19, 2020·Dalton Transactions : an International Journal of Inorganic Chemistry·Peter M ChappleYann Sarazin
Sep 12, 2020·Dalton Transactions : an International Journal of Inorganic Chemistry·Joanna HammoudYann Sarazin
Dec 10, 2019·Chemical Science·Lucia GarciaMichael S Hill
Jun 17, 2020·Chemistry : a European Journal·Cameron JonesLaurent Maron
Sep 9, 2020·Angewandte Chemie·Xiaohong LiQian Zhang
Oct 28, 2020·Dalton Transactions : an International Journal of Inorganic Chemistry·Louis J MorrisMary F Mahon
Feb 2, 2021·European Journal of Organic Chemistry·Harry C Sample, Mathias O Senge
Jun 3, 2021·Chemical Communications : Chem Comm·Thomas HöllerhageJun Okuda
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Jun 15, 2021·Chemical Science·Peter M ChappleYann Sarazin
Aug 28, 2021·Chemical Reviews·Matthew M D RoyEric Rivard
Nov 27, 2021·Chemistry, an Asian Journal·Sudip BaguliDebabrata Mukherjee

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