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Title: Phenanthrene synthesis via chromium-catalyzed annulation of 2-biaryl grignard reagents and alkynes
Authors: Yan, Jianming
Yoshikai, Naohiko
Keywords: Grignard Reagents
Phenanthrene Synthesis
Issue Date: 2017
Source: Yan, J., & Yoshikai, N. (2017). Phenanthrene synthesis via chromium-catalyzed annulation of 2-biaryl grignard reagents and alkynes. Organic Letters, 19(24), 6630-6633. doi:10.1021/acs.orglett.7b03342
Series/Report no.: Organic Letters
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.
ISSN: 1523-7060
DOI: 10.1021/acs.orglett.7b03342
Rights: © 2017 American Chemical Society. This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see
Fulltext Permission: open
Fulltext Availability: With Fulltext
Appears in Collections:SPMS Journal Articles

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