Base-Free Palladium-Catalyzed Synthesis of 2-Alkoxy-1,3-Dienes from Primary Propargyl Carbonates with Benzyl Alcohols

Although several methods have been reported for the synthesis of 1,3-diene skeletons from propargyl esters, only a few are effective for the synthesis of 2-alkoxy-1,3-dienes. Herein, we report a convenient palladium-catalyzed synthesis of these compounds using primary propargyl carbonates and benzyl alcohols. Mono-substituted 1,3-dienes were synthesized in up to 80% yield using various benzyl alcohols. Furthermore, the robustness and versatility of this method were demonstrated through a gram-scale synthesis and a one-pot reaction.

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Publication Details

Journal
Synlett
Published
2026-10-15
DOI
https://doi.org/10.1055/a-2983-1983
Primary Topic
Catalytic Cross-Coupling Reactions
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article
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article

Base-Free Palladium-Catalyzed Synthesis of 2-Alkoxy-1,3-Dienes from Primary Propargyl Carbonates with Benzyl Alcohols

Shinsuke Inagi, Kosuke Sato, Yuichiro Tokoro, Toshio Koizumi et al.
Synlett
Catalytic Cross-Coupling Reactions
article

Base-Free Palladium-Catalyzed Synthesis of 2-Alkoxy-1,3-Dienes from Primary Propargyl Carbonates with Benzyl Alcohols

Shinsuke Inagi, Kosuke Sato, Yuichiro Tokoro, Toshio Koizumi, Yoichiro Eriguchi, Masayuki Munemoto, Shin-Ichi Yamamoto
article en

Abstract

Although several methods have been reported for the synthesis of 1,3-diene skeletons from propargyl esters, only a few are effective for the synthesis of 2-alkoxy-1,3-dienes. Herein, we report a convenient palladium-catalyzed synthesis of these compounds using primary propargyl carbonates and benzyl alcohols. Mono-substituted 1,3-dienes were synthesized in up to 80% yield using various benzyl alcohols. Furthermore, the robustness and versatility of this method were demonstrated through a gram-scale synthesis and a one-pot reaction.

Synlett
Institute of Science Tokyo (JP), Ministry of Defense (JP), National Defense Academy of Japan (JP)
Openalex Percentile: Top 26%
Catalytic Cross-Coupling Reactions
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