Literature DB >> 29265668

Direct Annulation between Aryl Iodides and Epoxides through Palladium/Norbornene Cooperative Catalysis.

Renhe Li1, Guangbin Dong1.   

Abstract

Herein we report a direct annulation between aryl iodides and epoxides through palladium/norbornene (Pd/NBE) cooperative catalysis. An iso-propyl ester substituted NBE was found to be most efficient to suppress the formation of multiple-NBE-insertion byproducts and affords the desired 2,3-dihydrobenzofuran derivatives in 44-99 % yields. The reaction is scalable and tolerates a range of functional groups. Asymmetric synthesis is realized using an enantiopure epoxide. Application of this method into a concise synthesis of insecticide fufenozide is demonstrated.
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  annulation; cooperative catalysis; epoxides; norbornene; palladium

Year:  2018        PMID: 29265668     DOI: 10.1002/anie.201712393

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


  11 in total

1.  Redox-Neutral ortho Functionalization of Aryl Boroxines via Palladium/Norbornene Cooperative Catalysis.

Authors:  Renhe Li; Feipeng Liu; Guangbin Dong
Journal:  Chem       Date:  2019-03-07       Impact factor: 22.804

2.  Palladium/Norbornene Cooperative Catalysis.

Authors:  Jianchun Wang; Guangbin Dong
Journal:  Chem Rev       Date:  2019-04-25       Impact factor: 60.622

3.  Palladium-catalyzed asymmetric annulation between aryl iodides and racemic epoxides using a chiral norbornene cocatalyst.

Authors:  Renhe Li; Feipeng Liu; Guangbin Dong
Journal:  Org Chem Front       Date:  2018-09-25       Impact factor: 5.281

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

Authors:  Renhe Li; Guangbin Dong
Journal:  Angew Chem Int Ed Engl       Date:  2021-11-10       Impact factor: 15.336

5.  Palladium/Norbornene-Catalyzed Indenone Synthesis from Simple Aryl Iodides: Concise Syntheses of Pauciflorol F and Acredinone A.

Authors:  Feipeng Liu; Zhe Dong; Jianchun Wang; Guangbin Dong
Journal:  Angew Chem Int Ed Engl       Date:  2019-01-16       Impact factor: 15.336

6.  Modular ipso/ ortho Difunctionalization of Aryl Bromides via Palladium/Norbornene Cooperative Catalysis.

Authors:  Zhe Dong; Gang Lu; Jianchun Wang; Peng Liu; Guangbin Dong
Journal:  J Am Chem Soc       Date:  2018-06-27       Impact factor: 15.419

Review 7.  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

8.  Unexpected ortho-Heck Reaction under the Catellani Conditions.

Authors:  Alexander J Rago; Guangbin Dong
Journal:  Org Lett       Date:  2020-04-02       Impact factor: 6.005

9.  Redox-neutral ortho-C-H amination of pinacol arylborates via palladium(ii)/norbornene catalysis for aniline synthesis.

Authors:  Shuqing Chen; Peng Wang; Hong-Gang Cheng; Chihui Yang; Qianghui Zhou
Journal:  Chem Sci       Date:  2019-07-23       Impact factor: 9.825

10.  Recyclable Ruthenium Catalyst for Distal meta-C-H Activation.

Authors:  Isaac Choi; Valentin Müller; Yanhui Wang; Kai Xue; Rositha Kuniyil; Loren B Andreas; Volker Karius; Johan G Alauzun; Lutz Ackermann
Journal:  Chemistry       Date:  2020-10-22       Impact factor: 5.236

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