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Literature DB >> 25156018

Gold(I)-catalyzed diazo coupling: strategy towards alkene formation and tandem benzannulation.

Daming Zhang¹, Guangyang Xu, Dong Ding, Chenghao Zhu, Jian Li, Jiangtao Sun.

Abstract

A gold(I)-catalyzed cross-coupling of diazo compounds to afford tetrasubstituted alkenes has been developed by taking advantage of a trivial electronic difference between two diazo substrates. A N-heterocyclic-carbene-derived gold complex is the most effective catalyst for this transformation. Based on this new strategy, a gold(I)-initiated benzannulation has been achieved through a tandem reaction involving a diazo cross-coupling, 6π electrocyclization, and oxidative aromatization.

Entities: Chemical

Keywords: alkenes; annulations; cross-coupling; diazo compounds; gold

Year: 2014 PMID： 25156018 DOI： 10.1002/anie.201406712

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

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Cited

8 in total

1. Catalytic Divergent [3+3]- and [3+2]-Cycloaddition by Discrimination Between Diazo Compounds.

Authors: Yongming Deng; Lynée A Massey; Yeray A Rodriguez Núñez; Hadi Arman; Michael P Doyle
Journal: Angew Chem Int Ed Engl Date: 2017-08-24 Impact factor: 15.336

2. Z-Selective iridium-catalyzed cross-coupling of allylic carbonates and α-diazo esters.

Authors: Bryce N Thomas; Patrick J Moon; Shengkang Yin; Alex Brown; Rylan J Lundgren
Journal: Chem Sci Date: 2017-10-24 Impact factor: 9.825

3. Gold-catalyzed stereoselective dearomatization/metal-free aerobic oxidation: access to 3-substituted indolines/oxindoles.

Authors: Kai Liu; Guangyang Xu; Jiangtao Sun
Journal: Chem Sci Date: 2017-11-06 Impact factor: 9.825

8. Reactivity of Stabilized Vinyldiazo Compounds toward Alkenyl- and Alkynylsilanes under Gold Catalysis: Regio- and Stereoselective Synthesis of Skipped Dienes and Enynes.

Authors: Olaya Bernardo; Kota Yamamoto; Israel Fernández; Luis A López
Journal: Org Lett Date: 2021-05-13 Impact factor: 6.005

8 in total

Gold(I)-catalyzed diazo coupling: strategy towards alkene formation and tandem benzannulation.

1. Catalytic Divergent [3+3]- and [3+2]-Cycloaddition by Discrimination Between Diazo Compounds.

2. Z-Selective iridium-catalyzed cross-coupling of allylic carbonates and α-diazo esters.

3. Gold-catalyzed stereoselective dearomatization/metal-free aerobic oxidation: access to 3-substituted indolines/oxindoles.

4. A Catalytic Cross-Olefination of Diazo Compounds with Sulfoxonium Ylides.

5. Ionization of gold (γ-methoxy)vinyl complexes generates reactive gold vinyl carbene complexes.

6. Origins of unique gold-catalysed chemo- and site-selective C-H functionalization of phenols with diazo compounds.

7. Triarylborane-Catalyzed Alkenylation Reactions of Aryl Esters with Diazo Compounds.

8. Reactivity of Stabilized Vinyldiazo Compounds toward Alkenyl- and Alkynylsilanes under Gold Catalysis: Regio- and Stereoselective Synthesis of Skipped Dienes and Enynes.