A novel and efficient synthesis of phenanthrene derivatives via palladium/norbornadiene-catalyzed domino one-pot reaction

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Abstract

Herein we report a novel palladium-catalyzed reaction that results in phenanthrene derivatives using aryl iodides, ortho-bromobenzoyl chlorides and norbornadiene in one pot. This dramatic transformation undergoes ortho-C–H activation, decarbonylation and subsequent a retro-Diels–Alder process. Pleasantly, this protocol has a wider substrate range, shorter reaction times and higher yields of products than previously reported methods.

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Author and article information

Contributors

Nian-Guang Li

Zhi-Hao Shi

Ilan Marek: Role: Associate Editor

Journal

Journal ID (nlm-ta): Beilstein J Org Chem

Journal ID (iso-abbrev): Beilstein J Org Chem

Title: Beilstein Journal of Organic Chemistry

Publisher: Beilstein-Institut (Trakehner Str. 7-9, 60487 Frankfurt am Main, Germany )

ISSN (Electronic): 1860-5397

Publication date Collection: 2019

Publication date (Electronic): 31 January 2019

Volume: 15

Pages: 291-298

Affiliations

[1 ]National and Local Collaborative Engineering Center of Chinese Medicinal Resources Industrialization and Formulae Innovative Medicine, Jiangsu Collaborative Innovation Center of Chinese Medicinal Resources Industrialization, Jiangsu Key Laboratory for High Technology Research of TCM Formulae, Nanjing University of Chinese Medicine, Nanjing 210023, China

[2 ]Department of Nuclear Medicine, Nanjing First Hospital, Nanjing Medical University, Nanjing 21006, China

[3 ]Department of Organic Chemistry, China Pharmaceutical University, Nanjing 211198, China

[4 ]College of Pharmacy and Shaanxi Collaborative Innovation Center of Chinese Medicinal Resources Industrialization, Shaanxi University of Chinese Medicine, Xi’an 712046, Shaanxi Province, China

Article

DOI: 10.3762/bjoc.15.26

PMC ID: 6369988

SO-VID: 2237ae12-e0b8-4554-a709-97ad8ad2f782

License:

This is an Open Access article under the terms of the Creative Commons Attribution License ( http://creativecommons.org/licenses/by/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the authors and source are credited.

The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc)

History

Date received : 18 October 2018

Date accepted : 18 January 2019

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