Mild and Stereoselective Synthesis of (1E,3E)-Dienes through Silver(I)-Catalyzed β-Hydride Migration from Allylic α-Diazo Esters

Marcus M. Sá; Pedro A. M. Moro; Theo V. C. Russo; Vinicius C. Port; Giovanni F. Caramori

doi:10.1055/a-2369-3961

Synthesis, Inhaltsverzeichnis

Synthesis 2024; 56(24): 3741-3751
DOI: 10.1055/a-2369-3961

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Recent Advancements in The Chemistry of Diazo Compounds

Mild and Stereoselective Synthesis of (1E,3E)-Dienes through Silver(I)-Catalyzed β-Hydride Migration from Allylic α-Diazo Esters

Marcus M. Sá∗

^aMESOLab (Laboratory of Methodology and Organic Synthesis), Departamento de Química, Universidade Federal de Santa Catarina, 88040-900 Florianópolis-SC, Brazil

,

Pedro A. M. Moro

^aMESOLab (Laboratory of Methodology and Organic Synthesis), Departamento de Química, Universidade Federal de Santa Catarina, 88040-900 Florianópolis-SC, Brazil

,

Theo V. C. Russo

^aMESOLab (Laboratory of Methodology and Organic Synthesis), Departamento de Química, Universidade Federal de Santa Catarina, 88040-900 Florianópolis-SC, Brazil

,

Vinicius C. Port

^bGEEMM (Molecular Electronic Structure and Materials Group), Departamento de Química, Universidade Federal de Santa Catarina, 88040-900 Florianópolis-SC, Brazil

,

Giovanni F. Caramori

^bGEEMM (Molecular Electronic Structure and Materials Group), Departamento de Química, Universidade Federal de Santa Catarina, 88040-900 Florianópolis-SC, Brazil

› Institutsangaben

Abstract

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Abstract

A mild procedure for the diastereoselective preparation of functionalized 1,3-dienes and their synthetic versatility are described herein. The silver-catalyzed decomposition of α-diazo-γ,δ-unsaturated esters through β-hydride migration at room temperature resulted in the stereoselective formation of 12 conjugated (1E,3E)-dienes. Further synthetic post-modifications included intramolecular Heck reaction and hydrogenation, leading to a novel substituted indene and an aliphatic diester, respectively. To rationalize the observed reaction outcome, a computational investigation of the mechanisms was conducted, emphasizing the importance of factors such as metallocarbenoid stability, substituent effects, and microkinetics simulations to better understand the reaction intricacies.

Key words

α-diazo carbonyl compounds - silver-catalyzed reaction - β-hydride migration - 1,3-dienes - stereoselective catalysis - computational methods

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