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Literature DB >> 31744291

Direct Vicinal Difunctionalization of Thiophenes Enabled by the Palladium/Norbornene Cooperative Catalysis.

Renhe Li¹, Yun Zhou¹, Xiaolong Xu¹, Guangbin Dong¹.

Abstract

Herein we report a direct vicinal difunctionalization of thiophenes via the palladium/norbornene (Pd/NBE) cooperative catalysis. A series of mono- and disubstituted thiophenes can be difunctionalized site-selectively and regioselectively at the C4 and C5 positions in good yields, enabled by an arsine ligand and a unique amide-based NBE. The synthetic utility has been shown in derivatizations of complex bioactive compounds and an open-flask gram-scale preparation. Preliminary results have been obtained in the difunctionalization of furans and a direct C4-selective arylation of 2-substituted thiophenes.

Entities: Chemical Disease Species

Year: 2019 PMID： 31744291 PMCID： PMC7075341 DOI： 10.1021/jacs.9b10857

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

46 in total

1. C-H arylation of pyridines: high regioselectivity as a consequence of the electronic character of C-H bonds and heteroarene ring.

Authors: Pengfei Guo; Jung Min Joo; Souvik Rakshit; Dalibor Sames
Journal: J Am Chem Soc Date: 2011-09-22 Impact factor: 15.419

2. Selectively substituted thiophenes and indoles by a tandem palladium-catalyzed multicomponent reaction.

Authors: Koichi Mitsudo; Praew Thansandote; Thorsten Wilhelm; Brian Mariampillai; Mark Lautens
Journal: Org Lett Date: 2006-08-31 Impact factor: 6.005

3. C-H activation for the construction of C-B bonds.

Authors: Ibraheem A I Mkhalid; Jonathan H Barnard; Todd B Marder; Jaclyn M Murphy; John F Hartwig
Journal: Chem Rev Date: 2010-02-10 Impact factor: 60.622

4. Synthesis of Fluorescent Indazoles by Palladium-Catalyzed Benzannulation of Pyrazoles with Alkynes.

Authors: Og Soon Kim; Jin Hyeok Jang; Hyun Tae Kim; Su Jin Han; Gavin Chit Tsui; Jung Min Joo
Journal: Org Lett Date: 2017-03-08 Impact factor: 6.005

5. Site-Selectivity Control in Organic Reactions: A Quest To Differentiate Reactivity among the Same Kind of Functional Groups.

Authors: Zhongxing Huang; Guangbin Dong
Journal: Acc Chem Res Date: 2017-03-21 Impact factor: 22.384

Review 2. Structurally Modified Norbornenes: A Key Factor to Modulate Reaction Selectivity in the Palladium/Norbornene Cooperative Catalysis.

Authors: Renhe Li; Guangbin Dong
Journal: J Am Chem Soc Date: 2020-10-05 Impact factor: 15.419

3. S,O-Ligand Promoted meta-C-H Arylation of Anisole Derivatives via Palladium/Norbornene Catalysis.

Authors: Verena Sukowski; Manuela van Borselen; Simon Mathew; M Ángeles Fernández-Ibáñez
Journal: Angew Chem Int Ed Engl Date: 2022-06-21 Impact factor: 16.823

3 in total

Direct Vicinal Difunctionalization of Thiophenes Enabled by the Palladium/Norbornene Cooperative Catalysis.

1. C-H arylation of pyridines: high regioselectivity as a consequence of the electronic character of C-H bonds and heteroarene ring.

2. Selectively substituted thiophenes and indoles by a tandem palladium-catalyzed multicomponent reaction.

3. C-H activation for the construction of C-B bonds.

4. Synthesis of Fluorescent Indazoles by Palladium-Catalyzed Benzannulation of Pyrazoles with Alkynes.

5. Site-Selectivity Control in Organic Reactions: A Quest To Differentiate Reactivity among the Same Kind of Functional Groups.

6. Palladium-catalyzed direct 2-alkylation of indoles by norbornene-mediated regioselective cascade C-H activation.

7. Palladium-catalyzed multiple arylation of thiophenes.

8. Ortho C-H Acylation of Aryl Iodides by Palladium/Norbornene Catalysis.

9. Ligand-controlled Regiodivergent C-H Alkenylation of Pyrazoles and its Application to the Synthesis of Indazoles.

10. Ag(I)-C-H Activation Enables Near-Room-Temperature Direct α-Arylation of Benzo[ b]thiophenes.

1. Redox-Neutral Vicinal Difunctionalization of Five-Membered Heteroarenes with Dual Electrophiles.

Review 2. Structurally Modified Norbornenes: A Key Factor to Modulate Reaction Selectivity in the Palladium/Norbornene Cooperative Catalysis.

3. S,O-Ligand Promoted meta-C-H Arylation of Anisole Derivatives via Palladium/Norbornene Catalysis.