Phenanthrene Synthesis by Palladium(II)-Catalyzed γ-C(sp)-H Arylation, Cyclization, and Migration Tandem Reaction.

Org Lett

Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education, College of Chemistry & Materials Science, National Demonstration Center for Experimental Chemistry Education , Northwest University, Xi'an 710127 , P. R. China.

Published: January 2019

Phenanthrene is an important structural motif in chemistry and materials science, and many synthetic routes have been developed to construct its skeleton. However, synthesis of unsymmetric phenanthrenes remains a challenge. Here, an efficient one-pot tandem reaction for the preparation of phenanthrenes via sequential γ-C(sp)-H arylation, cationic cyclization, dehydration, and 1,2-migration was developed. A wide range of symmetric and unsymmetric phenanthrenes with diversified functional groups were synthesized with good to excellent yields.

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http://dx.doi.org/10.1021/acs.orglett.8b03511DOI Listing

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