Phenanthrene Synthesis via Chromium-Catalyzed Annulation of 2-Biaryl Grignard Reagents and Alkynes

Jianming Yan, Naohiko Yoshikai

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44 Citations (Scopus)

Abstract

A chromium/2,2′-bipyridine-catalyzed annulation reaction of 2-biarylmagnesium reagents with alkynes is reported. The reaction is applicable to a variety of aryl- and/or alkyl-substituted internal alkynes as well as 2-biaryl and related Grignard reagents, thus affording phenanthrene derivatives in moderate to good yields. The reaction proceeds at the expense of excess alkyne as a hydrogen acceptor and thus does not need an external oxidant. Deuterium-labeling experiments shed light on the reaction mechanism, which likely involves multiple intramolecular C-H activation processes on chromium.

Original languageEnglish
Pages (from-to)6630-6633
Number of pages4
JournalOrganic Letters
Volume19
Issue number24
DOIs
Publication statusPublished - 2017 Dec 15

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