Synthesis of Multideuterated (Hetero)aryl Bromides by Ag(I)-Catalyzed H/D Exchange

Guang Qi Hu; Jing Wen Bai; En Ci Li; Kai Hui Liu; Fei Fei Sheng; Hong Hai Zhang

doi:10.1021/acs.orglett.0c04139

Synthesis of Multideuterated (Hetero)aryl Bromides by Ag(I)-Catalyzed H/D Exchange

Guang Qi Hu, Jing Wen Bai, En Ci Li, Kai Hui Liu, Fei Fei Sheng, Hong Hai Zhang

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20 Scopus citations

Abstract

Deterium-labeled (hetero)aryl bromide is one of the most widespread applicable motifs to achieve important deuterated architectures for various scientific applications. Traditionally, these deterium-labeled (hetero)aryl bromides are commonly prepared via multistep syntheses. Herein, we disclose a direct H/D exchange protocol for deuteration of (hetero)aryl bromides using Ag2CO3 as catalyst and D2O as deuterium source. This protocol is highly efficient, simply manipulated, and appliable for deuterium-labeling of over 55 (hetero)aryl bromides including bioactive druglike molecules and key intermediates of functional materials. In addition, this method showed distinguishing site-selectivity toward the existing transition-metal-catalyzed HIE process, leading to multideuterated (hetero)aryl bromides in one step.

Original language	English
Pages (from-to)	1554-1560
Number of pages	7
Journal	Organic Letters
Volume	23
Issue number	5
DOIs	https://doi.org/10.1021/acs.orglett.0c04139
State	Published - Mar 5 2021
Externally published	Yes

Funding

We thank the National Natural Science Foundation of China (Grant Numbers 21704041, 22075135), Six Talent Peaks Project in Jiangsu Province (Grant No. XCL-027), and Nanjing Scientific Research Foundation for Returned Scholars for support.

Funders	Funder number
Nanjing Scientific Research Foundation for Returned Scholars
National Natural Science Foundation of China	21704041, 22075135
Six Talent Peaks Project in Jiangsu Province	XCL-027

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10.1021/acs.orglett.0c04139

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title = "Synthesis of Multideuterated (Hetero)aryl Bromides by Ag(I)-Catalyzed H/D Exchange",

abstract = "Deterium-labeled (hetero)aryl bromide is one of the most widespread applicable motifs to achieve important deuterated architectures for various scientific applications. Traditionally, these deterium-labeled (hetero)aryl bromides are commonly prepared via multistep syntheses. Herein, we disclose a direct H/D exchange protocol for deuteration of (hetero)aryl bromides using Ag2CO3 as catalyst and D2O as deuterium source. This protocol is highly efficient, simply manipulated, and appliable for deuterium-labeling of over 55 (hetero)aryl bromides including bioactive druglike molecules and key intermediates of functional materials. In addition, this method showed distinguishing site-selectivity toward the existing transition-metal-catalyzed HIE process, leading to multideuterated (hetero)aryl bromides in one step.",

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T1 - Synthesis of Multideuterated (Hetero)aryl Bromides by Ag(I)-Catalyzed H/D Exchange

AU - Hu, Guang Qi

AU - Bai, Jing Wen

AU - Li, En Ci

AU - Liu, Kai Hui

AU - Sheng, Fei Fei

AU - Zhang, Hong Hai

PY - 2021/3/5

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N2 - Deterium-labeled (hetero)aryl bromide is one of the most widespread applicable motifs to achieve important deuterated architectures for various scientific applications. Traditionally, these deterium-labeled (hetero)aryl bromides are commonly prepared via multistep syntheses. Herein, we disclose a direct H/D exchange protocol for deuteration of (hetero)aryl bromides using Ag2CO3 as catalyst and D2O as deuterium source. This protocol is highly efficient, simply manipulated, and appliable for deuterium-labeling of over 55 (hetero)aryl bromides including bioactive druglike molecules and key intermediates of functional materials. In addition, this method showed distinguishing site-selectivity toward the existing transition-metal-catalyzed HIE process, leading to multideuterated (hetero)aryl bromides in one step.

AB - Deterium-labeled (hetero)aryl bromide is one of the most widespread applicable motifs to achieve important deuterated architectures for various scientific applications. Traditionally, these deterium-labeled (hetero)aryl bromides are commonly prepared via multistep syntheses. Herein, we disclose a direct H/D exchange protocol for deuteration of (hetero)aryl bromides using Ag2CO3 as catalyst and D2O as deuterium source. This protocol is highly efficient, simply manipulated, and appliable for deuterium-labeling of over 55 (hetero)aryl bromides including bioactive druglike molecules and key intermediates of functional materials. In addition, this method showed distinguishing site-selectivity toward the existing transition-metal-catalyzed HIE process, leading to multideuterated (hetero)aryl bromides in one step.

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Synthesis of Multideuterated (Hetero)aryl Bromides by Ag(I)-Catalyzed H/D Exchange

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