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

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

37 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	4349-4352
Number of pages	4
Journal	Organometallics
Volume	33
Issue number	17
DOIs	https://doi.org/10.1021/om500647h
Publication status	Published - Sept 8 2014

All Science Journal Classification (ASJC) codes

Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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10.1021/om500647h

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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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T1 - Catalytic C-F bond hydrogenolysis of fluoroaromatics by [(η5-C5Me5)RhI(2,2′-bipyridine)]

AU - Nakai, Hidetaka

AU - Jeong, Kihun

AU - Matsumoto, Takahiro

AU - Ogo, Seiji

PY - 2014/9/8

Y1 - 2014/9/8

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

Abstract

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