Synthesis of aryl-platinum dinuclear complexes via ortho C-H bond activation of phenol and transmetalation of arylboronic acid

Masahiko Ochiai; Kôichi Fukui; Satoshi Iwatsuki; Koji Ishihara; Kazuko Matsumoto

doi:10.1021/om050316l

Synthesis of aryl-platinum dinuclear complexes via ortho C-H bond activation of phenol and transmetalation of arylboronic acid

Masahiko Ochiai, Kôichi Fukui, Satoshi Iwatsuki, Koji Ishihara, Kazuko Matsumoto

School of Advanced Science and Engineering

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

28 Citations (Scopus)

Abstract

The reaction of the pivalamidate-bridged platinum(III) dinuclear complex [Pt₂(NH₃)₄(^tBuCONH) ₂(OH₂)₂]⁴⁺ with phenol in water gave 2-hydroxyphenyl platinum dinuclear complex [Pt₂(NH₃) ₄(^tBuCONH)₂(C₆H₄(OH))] ³⁺ via ortho C-H bond activation in the axial position. The identical compound and the analogous phenyl complex [Pt₂(NH₃₎ ₄(^tBuCONH)₂(C₆H₅)] ³⁺ could alternatively be synthesized from the reactions of [Pt ₂(NH₃)₄(^tBuCONH)₂(OH ₂)₂]⁴⁺ with the corresponding arylboronic acids via transmetalation. The reactivities of the novel aryl-Pt₂ compounds toward nucleophiles and the effect of UV light irradiation were investigated. The ESR spectra showed that the axial aryl-Pt bond is homolytically cleaved by UV-light irradiation to give the aryl radical and the Pt(III)-Pt(II) paramagnetic complex.

Original language	English
Pages (from-to)	5528-5536
Number of pages	9
Journal	Organometallics
Volume	24
Issue number	23
DOIs	https://doi.org/10.1021/om050316l
Publication status	Published - 2005 Nov 7

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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title = "Synthesis of aryl-platinum dinuclear complexes via ortho C-H bond activation of phenol and transmetalation of arylboronic acid",

abstract = "The reaction of the pivalamidate-bridged platinum(III) dinuclear complex [Pt2(NH3)4(tBuCONH) 2(OH2)2]4+ with phenol in water gave 2-hydroxyphenyl platinum dinuclear complex [Pt2(NH3) 4(tBuCONH)2(C6H4(OH))] 3+ via ortho C-H bond activation in the axial position. The identical compound and the analogous phenyl complex [Pt2(NH3) 4(tBuCONH)2(C6H5)] 3+ could alternatively be synthesized from the reactions of [Pt 2(NH3)4(tBuCONH)2(OH 2)2]4+ with the corresponding arylboronic acids via transmetalation. The reactivities of the novel aryl-Pt2 compounds toward nucleophiles and the effect of UV light irradiation were investigated. The ESR spectra showed that the axial aryl-Pt bond is homolytically cleaved by UV-light irradiation to give the aryl radical and the Pt(III)-Pt(II) paramagnetic complex.",

author = "Masahiko Ochiai and K{\^o}ichi Fukui and Satoshi Iwatsuki and Koji Ishihara and Kazuko Matsumoto",

year = "2005",

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T1 - Synthesis of aryl-platinum dinuclear complexes via ortho C-H bond activation of phenol and transmetalation of arylboronic acid

AU - Ochiai, Masahiko

AU - Fukui, Kôichi

AU - Iwatsuki, Satoshi

AU - Ishihara, Koji

AU - Matsumoto, Kazuko

PY - 2005/11/7

Y1 - 2005/11/7

N2 - The reaction of the pivalamidate-bridged platinum(III) dinuclear complex [Pt2(NH3)4(tBuCONH) 2(OH2)2]4+ with phenol in water gave 2-hydroxyphenyl platinum dinuclear complex [Pt2(NH3) 4(tBuCONH)2(C6H4(OH))] 3+ via ortho C-H bond activation in the axial position. The identical compound and the analogous phenyl complex [Pt2(NH3) 4(tBuCONH)2(C6H5)] 3+ could alternatively be synthesized from the reactions of [Pt 2(NH3)4(tBuCONH)2(OH 2)2]4+ with the corresponding arylboronic acids via transmetalation. The reactivities of the novel aryl-Pt2 compounds toward nucleophiles and the effect of UV light irradiation were investigated. The ESR spectra showed that the axial aryl-Pt bond is homolytically cleaved by UV-light irradiation to give the aryl radical and the Pt(III)-Pt(II) paramagnetic complex.

AB - The reaction of the pivalamidate-bridged platinum(III) dinuclear complex [Pt2(NH3)4(tBuCONH) 2(OH2)2]4+ with phenol in water gave 2-hydroxyphenyl platinum dinuclear complex [Pt2(NH3) 4(tBuCONH)2(C6H4(OH))] 3+ via ortho C-H bond activation in the axial position. The identical compound and the analogous phenyl complex [Pt2(NH3) 4(tBuCONH)2(C6H5)] 3+ could alternatively be synthesized from the reactions of [Pt 2(NH3)4(tBuCONH)2(OH 2)2]4+ with the corresponding arylboronic acids via transmetalation. The reactivities of the novel aryl-Pt2 compounds toward nucleophiles and the effect of UV light irradiation were investigated. The ESR spectra showed that the axial aryl-Pt bond is homolytically cleaved by UV-light irradiation to give the aryl radical and the Pt(III)-Pt(II) paramagnetic complex.

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