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Literature DB >> 28901774

Sulfoxonium Ylides as a Carbene Precursor in Rh(III)-Catalyzed C-H Acylmethylation of Arenes.

Youwei Xu^1,2, Xukai Zhou^1,2, Guangfan Zheng¹, Xingwei Li¹.

Abstract

Sulfoxonium ylides act as an efficient carbene precursor in rhodium(III)-catalyzed C-H acylmethlyation of a variety of arenes assisted by different chelating groups, and both aryl- and alkyl-substituted β-carbonyl sulfoxonium ylides are applicable. The system proceeded under redox-neutral conditions with a broad scope, high efficiency, and functional group tolerance.

Entities: Chemical

Year: 2017 PMID： 28901774 DOI： 10.1021/acs.orglett.7b02531

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

13 in total

1. Rhodium(III)-catalyzed C-H functionalization of C-alkenyl azoles with sulfoxonium ylides for the synthesis of bridgehead N-fused [5,6]-bicyclic heterocycles.

Authors: Gia L Hoang; Jonathan A Ellman
Journal: Tetrahedron Date: 2018-03-31 Impact factor: 2.457

2. Three-Component Coupling of Aldehydes, Aminopyrazoles, and Sulfoxonium Ylides via Rhodium(III)-Catalyzed Imidoyl C-H Activation: Synthesis of Pyrazolo[1,5- a]pyrimidines.

Authors: Gia L Hoang; Andrew D Streit; Jonathan A Ellman
Journal: J Org Chem Date: 2018-12-10 Impact factor: 4.354

3. Bond-Forming and -Breaking Reactions at Sulfur(IV): Sulfoxides, Sulfonium Salts, Sulfur Ylides, and Sulfinate Salts.

Authors: Daniel Kaiser; Immo Klose; Rik Oost; James Neuhaus; Nuno Maulide
Journal: Chem Rev Date: 2019-06-25 Impact factor: 60.622

4. Rhodium(III)-Catalyzed Imidoyl C-H Activation for Annulations to Azolopyrimidines.

Authors: Kim Søholm Halskov; Michael R Witten; Gia L Hoang; Brandon Q Mercado; Jonathan A Ellman
Journal: Org Lett Date: 2018-03-27 Impact factor: 6.005

Review 5. A comprehensive overview of directing groups applied in metal-catalysed C-H functionalisation chemistry.

Authors: Carlo Sambiagio; David Schönbauer; Remi Blieck; Toan Dao-Huy; Gerit Pototschnig; Patricia Schaaf; Thomas Wiesinger; Muhammad Farooq Zia; Joanna Wencel-Delord; Tatiana Besset; Bert U W Maes; Michael Schnürch
Journal: Chem Soc Rev Date: 2018-08-28 Impact factor: 54.564

6. Insights into the Activation Mode of α-Carbonyl Sulfoxonium Ylides in Rhodium-Catalyzed C-H Activation: A Theoretical Study.

Authors: Dianmin Zhang; Xiaofang He; Tao Yang; Song Liu
Journal: ChemistryOpen Date: 2022-02-24 Impact factor: 2.630

Sulfoxonium Ylides as a Carbene Precursor in Rh(III)-Catalyzed C-H Acylmethylation of Arenes.

1. Rhodium(III)-catalyzed C-H functionalization of C-alkenyl azoles with sulfoxonium ylides for the synthesis of bridgehead N-fused [5,6]-bicyclic heterocycles.

2. Three-Component Coupling of Aldehydes, Aminopyrazoles, and Sulfoxonium Ylides via Rhodium(III)-Catalyzed Imidoyl C-H Activation: Synthesis of Pyrazolo[1,5- a]pyrimidines.

3. Bond-Forming and -Breaking Reactions at Sulfur(IV): Sulfoxides, Sulfonium Salts, Sulfur Ylides, and Sulfinate Salts.

4. Rhodium(III)-Catalyzed Imidoyl C-H Activation for Annulations to Azolopyrimidines.

Review 5. A comprehensive overview of directing groups applied in metal-catalysed C-H functionalisation chemistry.

6. Insights into the Activation Mode of α-Carbonyl Sulfoxonium Ylides in Rhodium-Catalyzed C-H Activation: A Theoretical Study.

7. Selenonium ylides: synthesis, characterization, and applications to photo-induced cyclopropanation reactions.

Review 8. Sulfur-Based Ylides in Transition-Metal-Catalysed Processes.

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

10. Chemospecific Cyclizations of α-Carbonyl Sulfoxonium Ylides on Aryls and Heteroaryls.