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

^*この論文の責任著者

薬品製造学研究室

研究成果: ジャーナルへの寄稿 › 学術論文 › 査読

43 被引用数 (Scopus)

抄録

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.

本文言語	英語
ページ（範囲）	648-653
ページ数	6
ジャーナル	Organic Process Research and Development
巻	23
号	4
DOI	https://doi.org/10.1021/acs.oprd.8b00383
出版ステータス	出版済み - 2019/04/19

ASJC Scopus 主題領域

物理化学および理論化学
有機化学

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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",

month = apr,

day = "19",

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

language = "英語",

volume = "23",

pages = "648--653",

journal = "Organic Process Research and Development",

issn = "1083-6160",

publisher = "American Chemical Society",

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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

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