A practical and efficient method for late-stage deuteration of terminal alkynes with silver salt as catalyst

Ding Chuan Wu; Jing Wen Bai; Lei Guo; Guang Qi Hu; Kai Hui Liu; Fei Fei Sheng; Hong Hai Zhang; Zheng Yi Sun; Kang Shen; Xiang Liu

doi:10.1016/j.tetlet.2020.152807

A practical and efficient method for late-stage deuteration of terminal alkynes with silver salt as catalyst

Ding Chuan Wu, Jing Wen Bai, Lei Guo, Guang Qi Hu, Kai Hui Liu, Fei Fei Sheng, Hong Hai Zhang, Zheng Yi Sun, Kang Shen, Xiang Liu

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

13 Scopus citations

Abstract

A practical and efficient H/D exchange method for selective deuteration of terminal alkynes was disclosed. The reaction was simply performed with CF₃COOAg as catalyst at room temperature, affording products with high level of deuterium incorporation. The excellent site-selectivity and promising functional group tolerance of this protocol enabled deuteration of pharmaceuticals and nature product derivatives.

Original language	English
Article number	152807
Journal	Tetrahedron Letters
Volume	66
DOIs	https://doi.org/10.1016/j.tetlet.2020.152807
State	Published - Mar 2 2021
Externally published	Yes

Funding

We thank the National Natural Science Foundation of China (Grant Numbers 21704041), Six Talent Peaks Project in Jiangsu Province (Grant Numbers XCL-027) and Nanjing Scientific Research Foundation for Returned Scholars for support. We thank Kunlun Hong (Oak Ridge National Laboratory) for assistance with the preparation of the manuscript. We thank the National Natural Science Foundation of China (Grant Numbers 21704041), Six Talent Peaks Project in Jiangsu Province (Grant Numbers XCL-027) and Nanjing Scientific Research Foundation for Returned Scholars for support. We thank Kunlun Hong (Oak Ridge National Laboratory) for assistance with the preparation of the manuscript.

Funders	Funder number
Nanjing Scientific Research Foundation for Returned Scholars
Oak Ridge National Laboratory
National Natural Science Foundation of China	21704041
Six Talent Peaks Project in Jiangsu Province	XCL-027

Keywords

Late-stage deuteration
Silver salt
Terminal alkyne

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10.1016/j.tetlet.2020.152807

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abstract = "A practical and efficient H/D exchange method for selective deuteration of terminal alkynes was disclosed. The reaction was simply performed with CF3COOAg as catalyst at room temperature, affording products with high level of deuterium incorporation. The excellent site-selectivity and promising functional group tolerance of this protocol enabled deuteration of pharmaceuticals and nature product derivatives.",

keywords = "Late-stage deuteration, Silver salt, Terminal alkyne",

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AU - Wu, Ding Chuan

AU - Bai, Jing Wen

AU - Guo, Lei

AU - Hu, Guang Qi

AU - Liu, Kai Hui

AU - Sheng, Fei Fei

AU - Zhang, Hong Hai

AU - Sun, Zheng Yi

AU - Shen, Kang

AU - Liu, Xiang

PY - 2021/3/2

Y1 - 2021/3/2

N2 - A practical and efficient H/D exchange method for selective deuteration of terminal alkynes was disclosed. The reaction was simply performed with CF3COOAg as catalyst at room temperature, affording products with high level of deuterium incorporation. The excellent site-selectivity and promising functional group tolerance of this protocol enabled deuteration of pharmaceuticals and nature product derivatives.

AB - A practical and efficient H/D exchange method for selective deuteration of terminal alkynes was disclosed. The reaction was simply performed with CF3COOAg as catalyst at room temperature, affording products with high level of deuterium incorporation. The excellent site-selectivity and promising functional group tolerance of this protocol enabled deuteration of pharmaceuticals and nature product derivatives.

KW - Late-stage deuteration

KW - Silver salt

KW - Terminal alkyne

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DO - 10.1016/j.tetlet.2020.152807

M3 - Article

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

M1 - 152807

ER -

A practical and efficient method for late-stage deuteration of terminal alkynes with silver salt as catalyst

Abstract

Funding

Keywords

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