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Literature DB >> 24481783

Rhodium(II)-catalyzed nondirected oxidative alkenylation of arenes: arene loading at one equivalent.

Harit U Vora¹, Anthony P Silvestri, Casper J Engelin, Jin-Quan Yu.

Abstract

A bimetallic Rh(II) catalyst promoted the C-H alkenylation of simple arenes at 1.0 equivalent without the use of a directing group. A phosphine ligand as well as cooperative reoxidation of Rh(II) with Cu(TFA)2 and V2O5 proved essential in providing monoalkenylated products in good yields and selectivities, especially with di- and trisubstituted arenes.

Entities: Chemical Gene

Keywords: CH activation; alkenylation; bimetallic catalysts; homogeneous catalysis; rhodium

Mesh：

Substances：

Year: 2014 PMID： 24481783 DOI： 10.1002/anie.201310539

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

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Cited

7 in total

1. Palladium-Catalyzed, Site-Selective Direct Allylation of Aryl C-H Bonds by Silver-Mediated C-H Activation: A Synthetic and Mechanistic Investigation.

Authors: Sarah Yunmi Lee; John F Hartwig
Journal: J Am Chem Soc Date: 2016-11-14 Impact factor: 15.419

2. Enantioselective Dehydrogenative Heck Arylations of Trisubstituted Alkenes with Indoles to Construct Quaternary Stereocenters.

Authors: Chun Zhang; Celine B Santiago; Jennifer M Crawford; Matthew S Sigman
Journal: J Am Chem Soc Date: 2015-12-10 Impact factor: 15.419

3. Overcoming O-H Insertion to Para-Selective C-H Functionalization of Free Phenols: Rh(II)/Xantphos Catalyzed Geminal Difunctionalization of Diazo Compounds.

Authors: Yang Yang; Bin Lu; Guiqing Xu; Xiaoming Wang
Journal: ACS Cent Sci Date: 2022-04-20 Impact factor: 18.728

4. Preparation of tetrasubstituted olefins using mono or double aerobic direct C-H functionalization strategies: importance of steric effects.

Authors: Nicolas Gigant; François Quintin; Jan-E Bäckvall
Journal: J Org Chem Date: 2015-02-16 Impact factor: 4.354

Rhodium(II)-catalyzed nondirected oxidative alkenylation of arenes: arene loading at one equivalent.

1. Palladium-Catalyzed, Site-Selective Direct Allylation of Aryl C-H Bonds by Silver-Mediated C-H Activation: A Synthetic and Mechanistic Investigation.

2. Enantioselective Dehydrogenative Heck Arylations of Trisubstituted Alkenes with Indoles to Construct Quaternary Stereocenters.

3. Overcoming O-H Insertion to Para-Selective C-H Functionalization of Free Phenols: Rh(II)/Xantphos Catalyzed Geminal Difunctionalization of Diazo Compounds.

4. Preparation of tetrasubstituted olefins using mono or double aerobic direct C-H functionalization strategies: importance of steric effects.

5. Reversed reactivity of anilines with alkynes in the rhodium-catalysed C-H activation/carbonylation tandem.

6. Chrysomycin A Derivatives for the Treatment of Multi-Drug-Resistant Tuberculosis.

7. Non-directed Pd-catalysed electrooxidative olefination of arenes.