Palladium-catalyzed selective synthesis of 2-allyltetrazoles

Shin Kamijo; Tienan Jin; Yoshinori Yamamoto

doi:10.1021/jo026147l

Palladium-catalyzed selective synthesis of 2-allyltetrazoles

Shin Kamijo, Tienan Jin, Yoshinori Yamamoto

SCI - Research and Analytical Center for Giant Molecules

Research output: Contribution to journal › Article › peer-review

50 Citations (Scopus)

Abstract

The palladium-catalyzed three-component coupling (TCC) reaction of cyano compounds, allyl methyl carbonate, and trimethylsilyl azide under a catalytic amount of Pd₂(dba)₃·CHCl₃ (2.5 mol %) and tri(2-furyl)phosphine (10 mol %) gave various kinds of 2-allyltetrazoles in good to excellent yields. A π-allylpalladium azide complex is proposed as a key intermediate in the TCC reaction.

Original language	English
Pages (from-to)	7413-7417
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	67
Issue number	21
DOIs	https://doi.org/10.1021/jo026147l
Publication status	Published - 2002 Oct 18

ASJC Scopus subject areas

Organic Chemistry

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abstract = "The palladium-catalyzed three-component coupling (TCC) reaction of cyano compounds, allyl methyl carbonate, and trimethylsilyl azide under a catalytic amount of Pd2(dba)3·CHCl3 (2.5 mol %) and tri(2-furyl)phosphine (10 mol %) gave various kinds of 2-allyltetrazoles in good to excellent yields. A π-allylpalladium azide complex is proposed as a key intermediate in the TCC reaction.",

author = "Shin Kamijo and Tienan Jin and Yoshinori Yamamoto",

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AU - Jin, Tienan

AU - Yamamoto, Yoshinori

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N2 - The palladium-catalyzed three-component coupling (TCC) reaction of cyano compounds, allyl methyl carbonate, and trimethylsilyl azide under a catalytic amount of Pd2(dba)3·CHCl3 (2.5 mol %) and tri(2-furyl)phosphine (10 mol %) gave various kinds of 2-allyltetrazoles in good to excellent yields. A π-allylpalladium azide complex is proposed as a key intermediate in the TCC reaction.

AB - The palladium-catalyzed three-component coupling (TCC) reaction of cyano compounds, allyl methyl carbonate, and trimethylsilyl azide under a catalytic amount of Pd2(dba)3·CHCl3 (2.5 mol %) and tri(2-furyl)phosphine (10 mol %) gave various kinds of 2-allyltetrazoles in good to excellent yields. A π-allylpalladium azide complex is proposed as a key intermediate in the TCC reaction.

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

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Palladium-catalyzed selective synthesis of 2-allyltetrazoles

Abstract

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