Synthesis of 2‑Aryloxy-1,3-dienes from Phenols and Propargyl Carbonates

A convenient method for the synthesis of 1,3-dienes from readily available compounds is reported. 2-Aryoxy-1,3-dienes are produced stereoselectively by a nickel-catalyzed reaction of propargyl carbonates with phenols. Functional group tolerance is broad to allow iodo, formyl, and boryl groups. The r...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2019-01, Vol.141 (1), p.84-88
Main Authors: Ishida, Naoki, Hori, Yusaku, Okumura, Shintaro, Murakami, Masahiro
Format: Article
Language:English
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Summary:A convenient method for the synthesis of 1,3-dienes from readily available compounds is reported. 2-Aryoxy-1,3-dienes are produced stereoselectively by a nickel-catalyzed reaction of propargyl carbonates with phenols. Functional group tolerance is broad to allow iodo, formyl, and boryl groups. The resulting 1,3-dienes are of much synthetic value because they can participate in a wide variety of reactions, including the Diels–Alder reaction.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.8b11159