H-D Exchange Deuteration of Arenes at Room Temperature

Yoshinari Sawama; Akihiro Nakano; Takumi Matsuda; Takahiro Kawajiri; Tsuyoshi Yamada; Hironao Sajiki

doi:10.1021/acs.oprd.8b00383

H-D Exchange Deuteration of Arenes at Room Temperature

Yoshinari Sawama^*, Akihiro Nakano, Takumi Matsuda, Takahiro Kawajiri, Tsuyoshi Yamada, Hironao Sajiki

^*Corresponding author for this work

Synthetic and Medicinal Chemistry

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

43 Scopus citations

Abstract

Arene nuclei efficiently underwent the hydrogen (H)-deuterium (D) exchange reaction catalyzed by platinum group metals on carbon in a mixed solvent of 2-propanol and D ₂ O at room temperature to produce deuterium-labeled arenes. Platinum on carbon (Pt/C) and iridium on carbon (Ir/C) were applicable catalysts, and the various arenes bearing a carbonyl group, fluorine, phenolic hydroxy group, amino group, or phosphonic acid on the aromatic nucleus were effectively deuterated. Nonheating conditions are valuable for the scalable industrial preparation.

Original language	English
Pages (from-to)	648-653
Number of pages	6
Journal	Organic Process Research and Development
Volume	23
Issue number	4
DOIs	https://doi.org/10.1021/acs.oprd.8b00383
State	Published - 2019/04/19

Keywords

arene
deuteration
heterogeneous catalyst
platinum group metal
room temperature

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.oprd.8b00383

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title = "H-D Exchange Deuteration of Arenes at Room Temperature",

abstract = " Arene nuclei efficiently underwent the hydrogen (H)-deuterium (D) exchange reaction catalyzed by platinum group metals on carbon in a mixed solvent of 2-propanol and D 2 O at room temperature to produce deuterium-labeled arenes. Platinum on carbon (Pt/C) and iridium on carbon (Ir/C) were applicable catalysts, and the various arenes bearing a carbonyl group, fluorine, phenolic hydroxy group, amino group, or phosphonic acid on the aromatic nucleus were effectively deuterated. Nonheating conditions are valuable for the scalable industrial preparation.",

keywords = "arene, deuteration, heterogeneous catalyst, platinum group metal, room temperature",

author = "Yoshinari Sawama and Akihiro Nakano and Takumi Matsuda and Takahiro Kawajiri and Tsuyoshi Yamada and Hironao Sajiki",

note = "Publisher Copyright: {\textcopyright} 2019 American Chemical Society.",

year = "2019",

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day = "19",

doi = "10.1021/acs.oprd.8b00383",

language = "英語",

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TY - JOUR

T1 - H-D Exchange Deuteration of Arenes at Room Temperature

AU - Sawama, Yoshinari

AU - Nakano, Akihiro

AU - Matsuda, Takumi

AU - Kawajiri, Takahiro

AU - Yamada, Tsuyoshi

AU - Sajiki, Hironao

PY - 2019/4/19

Y1 - 2019/4/19

N2 - Arene nuclei efficiently underwent the hydrogen (H)-deuterium (D) exchange reaction catalyzed by platinum group metals on carbon in a mixed solvent of 2-propanol and D 2 O at room temperature to produce deuterium-labeled arenes. Platinum on carbon (Pt/C) and iridium on carbon (Ir/C) were applicable catalysts, and the various arenes bearing a carbonyl group, fluorine, phenolic hydroxy group, amino group, or phosphonic acid on the aromatic nucleus were effectively deuterated. Nonheating conditions are valuable for the scalable industrial preparation.

AB - Arene nuclei efficiently underwent the hydrogen (H)-deuterium (D) exchange reaction catalyzed by platinum group metals on carbon in a mixed solvent of 2-propanol and D 2 O at room temperature to produce deuterium-labeled arenes. Platinum on carbon (Pt/C) and iridium on carbon (Ir/C) were applicable catalysts, and the various arenes bearing a carbonyl group, fluorine, phenolic hydroxy group, amino group, or phosphonic acid on the aromatic nucleus were effectively deuterated. Nonheating conditions are valuable for the scalable industrial preparation.

KW - arene

KW - deuteration

KW - heterogeneous catalyst

KW - platinum group metal

KW - room temperature

UR - http://www.scopus.com/inward/record.url?scp=85061250687&partnerID=8YFLogxK

U2 - 10.1021/acs.oprd.8b00383

DO - 10.1021/acs.oprd.8b00383

M3 - 学術論文

AN - SCOPUS:85061250687

SN - 1083-6160

VL - 23

SP - 648

EP - 653

JO - Organic Process Research and Development

JF - Organic Process Research and Development

IS - 4

ER -

H-D Exchange Deuteration of Arenes at Room Temperature

Abstract

Keywords

ASJC Scopus subject areas

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