Multideuteration of Nitroaromatics by Silver-Catalyzed Hydrogen-Isotope Exchange

Jianbo Tang; Junhua Kong; Hui Xu; Zhi Jiang Jiang; Yifan She; Jianfei Bai; Bencan Tang; Jia Chen; Zhanghua Gao; Kun Gao

doi:10.1021/acs.joc.2c02618

Multideuteration of Nitroaromatics by Silver-Catalyzed Hydrogen-Isotope Exchange

Jianbo Tang, Junhua Kong, Hui Xu, Zhi Jiang Jiang, Yifan She, Jianfei Bai, Bencan Tang, Jia Chen, Zhanghua Gao, Kun Gao

Research output: Journal Publication › Article › peer-review

12 Citations (Scopus)

Abstract

Silver-catalyzed deuteration of nitroaromatics has been achieved using D₂O as the deuterium source. Distinct from the well-established directing group-guided hydrogen-isotope exchange, this protocol showed an interesting deuteration pattern, where considerable deuterium accumulation was observed around the aromatic rings. Controlling experiments suggested that the deuteration was initiated by a silver-promoted C-H activation. Therefore, a tentative two-stage deuteration mechanism involving aryl-silver species was proposed to explain the deuteration on meta- and para-positions.

Original language	English
Pages (from-to)	1560-1567
Number of pages	8
Journal	Journal of Organic Chemistry
Volume	88
Issue number	3
DOIs	https://doi.org/10.1021/acs.joc.2c02618
Publication status	Published - 3 Feb 2023

ASJC Scopus subject areas

Organic Chemistry

Access to Document

10.1021/acs.joc.2c02618

Cite this

@article{cfe22e3df7b44b08ae5ffa3bd15627a0,

title = "Multideuteration of Nitroaromatics by Silver-Catalyzed Hydrogen-Isotope Exchange",

abstract = "Silver-catalyzed deuteration of nitroaromatics has been achieved using D2O as the deuterium source. Distinct from the well-established directing group-guided hydrogen-isotope exchange, this protocol showed an interesting deuteration pattern, where considerable deuterium accumulation was observed around the aromatic rings. Controlling experiments suggested that the deuteration was initiated by a silver-promoted C-H activation. Therefore, a tentative two-stage deuteration mechanism involving aryl-silver species was proposed to explain the deuteration on meta- and para-positions.",

author = "Jianbo Tang and Junhua Kong and Hui Xu and Jiang, \{Zhi Jiang\} and Yifan She and Jianfei Bai and Bencan Tang and Jia Chen and Zhanghua Gao and Kun Gao",

note = "Publisher Copyright: {\textcopyright} 2023 American Chemical Society.",

year = "2023",

month = feb,

day = "3",

doi = "10.1021/acs.joc.2c02618",

language = "English",

volume = "88",

pages = "1560--1567",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "3",

}

TY - JOUR

T1 - Multideuteration of Nitroaromatics by Silver-Catalyzed Hydrogen-Isotope Exchange

AU - Tang, Jianbo

AU - Kong, Junhua

AU - Xu, Hui

AU - Jiang, Zhi Jiang

AU - She, Yifan

AU - Bai, Jianfei

AU - Tang, Bencan

AU - Chen, Jia

AU - Gao, Zhanghua

AU - Gao, Kun

PY - 2023/2/3

Y1 - 2023/2/3

N2 - Silver-catalyzed deuteration of nitroaromatics has been achieved using D2O as the deuterium source. Distinct from the well-established directing group-guided hydrogen-isotope exchange, this protocol showed an interesting deuteration pattern, where considerable deuterium accumulation was observed around the aromatic rings. Controlling experiments suggested that the deuteration was initiated by a silver-promoted C-H activation. Therefore, a tentative two-stage deuteration mechanism involving aryl-silver species was proposed to explain the deuteration on meta- and para-positions.

AB - Silver-catalyzed deuteration of nitroaromatics has been achieved using D2O as the deuterium source. Distinct from the well-established directing group-guided hydrogen-isotope exchange, this protocol showed an interesting deuteration pattern, where considerable deuterium accumulation was observed around the aromatic rings. Controlling experiments suggested that the deuteration was initiated by a silver-promoted C-H activation. Therefore, a tentative two-stage deuteration mechanism involving aryl-silver species was proposed to explain the deuteration on meta- and para-positions.

UR - https://www.scopus.com/pages/publications/85146383551

U2 - 10.1021/acs.joc.2c02618

DO - 10.1021/acs.joc.2c02618

M3 - Article

AN - SCOPUS:85146383551

SN - 0022-3263

VL - 88

SP - 1560

EP - 1567

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 3

ER -

Multideuteration of Nitroaromatics by Silver-Catalyzed Hydrogen-Isotope Exchange

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this