Catalytic C-F bond hydrogenolysis of fluoroaromatics by [(η5-C5Me5)RhI(2,2′-bipyridine)]

Hidetaka Nakai; Kihun Jeong; Takahiro Matsumoto; Seiji Ogo

doi:10.1021/om500647h

Catalytic C-F bond hydrogenolysis of fluoroaromatics by [(η⁵-C₅Me₅)Rh^I(2,2′-bipyridine)]

Hidetaka Nakai, Kihun Jeong, Takahiro Matsumoto, Seiji Ogo

研究成果: ジャーナルへの寄稿 › 学術誌 › 査読

39 被引用数 (Scopus)

抄録

A new class of efficient catalyst, the Rh(I) complex [(η⁵-C₅Me₅)Rh^I(bpy)] (1; bpy = 2,2′-bipyridine), for the C-F bond hydrogenolysis of fluoroaromatics (C₆F₅CF₃, C₆F₆, C₆F₅H, and C₆F₅CH₃) is presented. The best turnover number of 380 for C₆F₆ is afforded by using 0.1 mol % of 1, 0.8 MPa of H₂, and 2 equiv of Et₂NH in CH₃CN at 25 °C. The successful isolation of the C-F bond cleavage product [(η⁵-C₅Me₅)Rh^III(bpy)(C₆F₅)](F) as a plausible intermediate of the catalytic hydrogenolysis of C₆F₆ by 1 is also described.

本文言語	英語
ページ（範囲）	4349-4352
ページ数	4
ジャーナル	Organometallics
巻	33
号	17
DOI	https://doi.org/10.1021/om500647h
出版ステータス	出版済み - 9月 8 2014

!!!All Science Journal Classification (ASJC) codes

物理化学および理論化学
有機化学
無機化学

文献へのアクセス

10.1021/om500647h

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引用スタイル

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title = "Catalytic C-F bond hydrogenolysis of fluoroaromatics by [(η5-C5Me5)RhI(2,2′-bipyridine)]",

abstract = "A new class of efficient catalyst, the Rh(I) complex [(η5-C5Me5)RhI(bpy)] (1; bpy = 2,2′-bipyridine), for the C-F bond hydrogenolysis of fluoroaromatics (C6F5CF3, C6F6, C6F5H, and C6F5CH3) is presented. The best turnover number of 380 for C6F6 is afforded by using 0.1 mol % of 1, 0.8 MPa of H2, and 2 equiv of Et2NH in CH3CN at 25 °C. The successful isolation of the C-F bond cleavage product [(η5-C5Me5)RhIII(bpy)(C6F5)](F) as a plausible intermediate of the catalytic hydrogenolysis of C6F6 by 1 is also described.",

author = "Hidetaka Nakai and Kihun Jeong and Takahiro Matsumoto and Seiji Ogo",

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AU - Nakai, Hidetaka

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AU - Matsumoto, Takahiro

AU - Ogo, Seiji

PY - 2014/9/8

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N2 - A new class of efficient catalyst, the Rh(I) complex [(η5-C5Me5)RhI(bpy)] (1; bpy = 2,2′-bipyridine), for the C-F bond hydrogenolysis of fluoroaromatics (C6F5CF3, C6F6, C6F5H, and C6F5CH3) is presented. The best turnover number of 380 for C6F6 is afforded by using 0.1 mol % of 1, 0.8 MPa of H2, and 2 equiv of Et2NH in CH3CN at 25 °C. The successful isolation of the C-F bond cleavage product [(η5-C5Me5)RhIII(bpy)(C6F5)](F) as a plausible intermediate of the catalytic hydrogenolysis of C6F6 by 1 is also described.

AB - A new class of efficient catalyst, the Rh(I) complex [(η5-C5Me5)RhI(bpy)] (1; bpy = 2,2′-bipyridine), for the C-F bond hydrogenolysis of fluoroaromatics (C6F5CF3, C6F6, C6F5H, and C6F5CH3) is presented. The best turnover number of 380 for C6F6 is afforded by using 0.1 mol % of 1, 0.8 MPa of H2, and 2 equiv of Et2NH in CH3CN at 25 °C. The successful isolation of the C-F bond cleavage product [(η5-C5Me5)RhIII(bpy)(C6F5)](F) as a plausible intermediate of the catalytic hydrogenolysis of C6F6 by 1 is also described.

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