Synthesis of Multisubstituted 1,2,3-Triazoles: Regioselective Formation and Reaction Mechanism

Tzu Ching Chi; Po Chun Yang; Shao Kung Hung; Hui Wen Wu; Hong Chi Wang; Hsin Kuan Liu; Li Wen Liu; Ho Hsuan Chou

doi:10.1021/acs.joc.3c02836

Synthesis of Multisubstituted 1,2,3-Triazoles: Regioselective Formation and Reaction Mechanism

Tzu Ching Chi, Po Chun Yang, Shao Kung Hung, Hui Wen Wu, Hong Chi Wang, Hsin Kuan Liu, Li Wen Liu, Ho Hsuan Chou

Department of Chemistry

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

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Abstract

A synthetically useful approach to functionalized triazoles is described via the reaction of β-carbonyl phosphonates and azides. 1,4- and 1,5-disubstituted and 1,4,5-trisubstituted triazoles can be regio- and chemoselectively accessed under mild conditions in good to excellent yields (31 examples, up to 99%). A mechanism is proposed that rationalizes the avoidance of the 4-phosphonate byproducts, which is aligned with crystallographic and experimental evidence.

Original language	English
Pages (from-to)	5401-5408
Number of pages	8
Journal	Journal of Organic Chemistry
Volume	89
Issue number	8
DOIs	https://doi.org/10.1021/acs.joc.3c02836
Publication status	Published - 2024 Apr 19

All Science Journal Classification (ASJC) codes

Organic Chemistry

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title = "Synthesis of Multisubstituted 1,2,3-Triazoles: Regioselective Formation and Reaction Mechanism",

abstract = "A synthetically useful approach to functionalized triazoles is described via the reaction of β-carbonyl phosphonates and azides. 1,4- and 1,5-disubstituted and 1,4,5-trisubstituted triazoles can be regio- and chemoselectively accessed under mild conditions in good to excellent yields (31 examples, up to 99%). A mechanism is proposed that rationalizes the avoidance of the 4-phosphonate byproducts, which is aligned with crystallographic and experimental evidence.",

author = "Chi, {Tzu Ching} and Yang, {Po Chun} and Hung, {Shao Kung} and Wu, {Hui Wen} and Wang, {Hong Chi} and Liu, {Hsin Kuan} and Liu, {Li Wen} and Chou, {Ho Hsuan}",

note = "Publisher Copyright: {\textcopyright} 2024 The Authors. Published by American Chemical Society",

year = "2024",

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doi = "10.1021/acs.joc.3c02836",

language = "English",

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T1 - Synthesis of Multisubstituted 1,2,3-Triazoles

T2 - Regioselective Formation and Reaction Mechanism

AU - Chi, Tzu Ching

AU - Yang, Po Chun

AU - Hung, Shao Kung

AU - Wu, Hui Wen

AU - Wang, Hong Chi

AU - Liu, Hsin Kuan

AU - Liu, Li Wen

AU - Chou, Ho Hsuan

PY - 2024/4/19

Y1 - 2024/4/19

N2 - A synthetically useful approach to functionalized triazoles is described via the reaction of β-carbonyl phosphonates and azides. 1,4- and 1,5-disubstituted and 1,4,5-trisubstituted triazoles can be regio- and chemoselectively accessed under mild conditions in good to excellent yields (31 examples, up to 99%). A mechanism is proposed that rationalizes the avoidance of the 4-phosphonate byproducts, which is aligned with crystallographic and experimental evidence.

AB - A synthetically useful approach to functionalized triazoles is described via the reaction of β-carbonyl phosphonates and azides. 1,4- and 1,5-disubstituted and 1,4,5-trisubstituted triazoles can be regio- and chemoselectively accessed under mild conditions in good to excellent yields (31 examples, up to 99%). A mechanism is proposed that rationalizes the avoidance of the 4-phosphonate byproducts, which is aligned with crystallographic and experimental evidence.

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M3 - Article

AN - SCOPUS:85189041894

SN - 0022-3263

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SP - 5401

EP - 5408

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 8

ER -

Synthesis of Multisubstituted 1,2,3-Triazoles: Regioselective Formation and Reaction Mechanism

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