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

Beilstein J Org Chem

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.

Published: January 2019

Herein we report a novel palladium-catalyzed reaction that results in phenanthrene derivatives using aryl iodides, -bromobenzoyl chlorides and norbornadiene in one pot. This dramatic transformation undergoes 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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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6369988PMC
http://dx.doi.org/10.3762/bjoc.15.26DOI Listing

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