Literature DB >> 19937624

Silicon- and tin-based cuprates: now catalytic in copper!

Andreas Weickgenannt1, Martin Oestreich.   

Abstract

Silicon- and tin-containing molecules are versatile building blocks in organic synthesis. A stalwart method for their preparation relies on the stoichiometric use of silicon- and tin-based cuprates, although a few copper(I)-catalyzed or even copper-free protocols have been known for decades. In this Concept, we describe our efforts towards copper(I)-catalyzed carbon--silicon and also carbon--tin bond formations using soft bis(triorganosilyl) and bis(triorganostannyl) zinc reagents as powerful sources of nucleophilic silicon and tin. Conjugate addition, allylic substitution, and carbon--carbon multiple bond functionalization is now catalytic in copper!

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Year:  2010        PMID: 19937624     DOI: 10.1002/chem.200902222

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  7 in total

1.  Synthesis of Silylated Cyclobutanone and Cyclobutene Derivatives Involving 1,4-Addition of Zinc-Based Silicon Nucleophiles.

Authors:  Ming Cui; Martin Oestreich
Journal:  Chemistry       Date:  2021-10-07       Impact factor: 5.020

2.  Activation of Si-Si Bonds for Copper(I)-Catalyzed Conjugate Silylation.

Authors:  Laura Iannazzo; Gary A Molander
Journal:  European J Org Chem       Date:  2012-09

Review 3.  Beyond Carbon: Enantioselective and Enantiospecific Reactions with Catalytically Generated Boryl- and Silylcopper Intermediates.

Authors:  Weichao Xue; Martin Oestreich
Journal:  ACS Cent Sci       Date:  2020-07-09       Impact factor: 14.553

4.  Stereospecific and Chemoselective Copper-Catalyzed Deaminative Silylation of Benzylic Ammonium Triflates.

Authors:  Jonas Scharfbier; Benjamin M Gross; Martin Oestreich
Journal:  Angew Chem Int Ed Engl       Date:  2019-12-04       Impact factor: 15.336

5.  Copper-Catalyzed Asymmetric Silylation of Propargyl Dichlorides: Access to Enantioenriched Functionalized Allenylsilanes.

Authors:  Zheng-Li Liu; Chao Yang; Qi-Yan Xue; Meng Zhao; Cui-Cui Shan; Yun-He Xu; Teck-Peng Loh
Journal:  Angew Chem Int Ed Engl       Date:  2019-10-04       Impact factor: 15.336

6.  Sodium silylsilanolate as a precursor of silylcopper species.

Authors:  Hiroki Yamagishi; Kenshiro Hitoshio; Jun Shimokawa; Hideki Yorimitsu
Journal:  Chem Sci       Date:  2022-03-21       Impact factor: 9.825

7.  Orbital energy mismatch engenders high-spin ground states in heterobimetallic complexes.

Authors:  Scott C Coste; Tyler J Pearson; Alison B Altman; Ryan A Klein; Brian A Finney; Michael Y Hu; E Ercan Alp; Bess Vlaisavljevich; Danna E Freedman
Journal:  Chem Sci       Date:  2020-09-01       Impact factor: 9.825

  7 in total

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