Pd-Catalyzed regio- and stereoselective allylic substitution of vinylethylene carbonates with 1,2,4-triazoles

Sardaraz Khan; Babar Hussain Shah; Can Zhao; Yong Jian Zhang

doi:10.1039/d2ob01156e

Pd-Catalyzed regio- and stereoselective allylic substitution of vinylethylene carbonates with 1,2,4-triazoles

Sardaraz Khan, Babar Hussain Shah, Can Zhao, Yong Jian Zhang^*

^*Corresponding author for this work

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

8 Scopus citations

Abstract

N ¹-Substituted 1,2,4-triazoles are ubiquitous skeletons in medicinal agents, agrochemicals, and organic materials. Herein, an efficient and practical method for the synthesis of N¹-allylated 1,2,4-triazoles via Pd-catalyzed allylic substitution of vinylethylene carbonates (VECs) with 1,2,4-triazoles has been developed. By using a catalyst generated in situ from Pd₂(dba)₃·CHCl₃ and DPPE under mild conditions, the process allows rapid access to N¹-allylated 1,2,4-triazoles bearing diverse functionalities in high yields with excellent N¹-selectivities, linear-selectivities, and Z-stereoselectivities.

Original language	English
Pages (from-to)	6532-6536
Number of pages	5
Journal	Organic and Biomolecular Chemistry
Volume	20
Issue number	33
DOIs	https://doi.org/10.1039/d2ob01156e
State	Published - 22 Jul 2022
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2022 The Royal Society of Chemistry.

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1039/d2ob01156e

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title = "Pd-Catalyzed regio- and stereoselective allylic substitution of vinylethylene carbonates with 1,2,4-triazoles",

abstract = "N 1-Substituted 1,2,4-triazoles are ubiquitous skeletons in medicinal agents, agrochemicals, and organic materials. Herein, an efficient and practical method for the synthesis of N1-allylated 1,2,4-triazoles via Pd-catalyzed allylic substitution of vinylethylene carbonates (VECs) with 1,2,4-triazoles has been developed. By using a catalyst generated in situ from Pd2(dba)3·CHCl3 and DPPE under mild conditions, the process allows rapid access to N1-allylated 1,2,4-triazoles bearing diverse functionalities in high yields with excellent N1-selectivities, linear-selectivities, and Z-stereoselectivities.",

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T1 - Pd-Catalyzed regio- and stereoselective allylic substitution of vinylethylene carbonates with 1,2,4-triazoles

AU - Khan, Sardaraz

AU - Shah, Babar Hussain

AU - Zhao, Can

AU - Zhang, Yong Jian

PY - 2022/7/22

Y1 - 2022/7/22

N2 - N 1-Substituted 1,2,4-triazoles are ubiquitous skeletons in medicinal agents, agrochemicals, and organic materials. Herein, an efficient and practical method for the synthesis of N1-allylated 1,2,4-triazoles via Pd-catalyzed allylic substitution of vinylethylene carbonates (VECs) with 1,2,4-triazoles has been developed. By using a catalyst generated in situ from Pd2(dba)3·CHCl3 and DPPE under mild conditions, the process allows rapid access to N1-allylated 1,2,4-triazoles bearing diverse functionalities in high yields with excellent N1-selectivities, linear-selectivities, and Z-stereoselectivities.

AB - N 1-Substituted 1,2,4-triazoles are ubiquitous skeletons in medicinal agents, agrochemicals, and organic materials. Herein, an efficient and practical method for the synthesis of N1-allylated 1,2,4-triazoles via Pd-catalyzed allylic substitution of vinylethylene carbonates (VECs) with 1,2,4-triazoles has been developed. By using a catalyst generated in situ from Pd2(dba)3·CHCl3 and DPPE under mild conditions, the process allows rapid access to N1-allylated 1,2,4-triazoles bearing diverse functionalities in high yields with excellent N1-selectivities, linear-selectivities, and Z-stereoselectivities.

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Pd-Catalyzed regio- and stereoselective allylic substitution of vinylethylene carbonates with 1,2,4-triazoles

Abstract

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