C–H Activation of the 5-(Pyridine-3-yloxy)isophthalic Acid to Construct Iridium, Rhodium, and Ruthenium Binuclear Metallocyclophanes

Philjae Kang; Yonggoon Jeon; Younghun Kim; Moon Gun Choi

doi:10.1002/bkcs.11543

C–H Activation of the 5-(Pyridine-3-yloxy)isophthalic Acid to Construct Iridium, Rhodium, and Ruthenium Binuclear Metallocyclophanes

Philjae Kang, Yonggoon Jeon, Younghun Kim, Moon Gun Choi

Department of Chemistry

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

Abstract

The multitopic ligand, 5-(pyridine-3-yloxy)isophthalic acid (m-POiPH₂, 1), containing two different coordination sites of pyridine and isophthalic acid linked by the C–O–C bond, is prepared. The reaction of 1 with half sandwich complexes of [Cp*Rh(OAc)₂] (Cp* = η⁵-C₅Me₅), [Cp*Ir(OAc)₂], and [(p-cymene)Ru(OAc)₂ afford the construction of binuclear metallocyclophanes [(Cp*Ir)₂(m-POiP)₂] (2), [(Cp*Rh)₂(m-POiP)₂ (3), and [((p-cymene)Ru)₂(m-POiP)₂] (4) in high yields. Crystal structures of 2, 3, and 4 illustrate binuclear metallocyclophanes constructed by cyclometallation by ortho-C–H activation and coordination of N-donor with metals which is confirmed by a single crystal X-ray diffraction (SC-XRD). Each metallocyclophanes shows unique packing structure by intermolecular hydrogen bonding; 2 and 3 shows 1D linear chain network, while the packing of 4 presents the 2D sheet.

Original language	English
Pages (from-to)	1030-1035
Number of pages	6
Journal	Bulletin of the Korean Chemical Society
Volume	39
Issue number	9
DOIs	https://doi.org/10.1002/bkcs.11543
Publication status	Published - 2018 Sept

Bibliographical note

Funding Information:
We would like to acknowledge the financial support from the Korea Institute of Materials Science (Project No.:PNK‐5620).

Publisher Copyright:
© 2018 Korean Chemical Society, Seoul & Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

All Science Journal Classification (ASJC) codes

Chemistry(all)

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title = "C–H Activation of the 5-(Pyridine-3-yloxy)isophthalic Acid to Construct Iridium, Rhodium, and Ruthenium Binuclear Metallocyclophanes",

abstract = "The multitopic ligand, 5-(pyridine-3-yloxy)isophthalic acid (m-POiPH2, 1), containing two different coordination sites of pyridine and isophthalic acid linked by the C–O–C bond, is prepared. The reaction of 1 with half sandwich complexes of [Cp*Rh(OAc)2] (Cp* = η5-C5Me5), [Cp*Ir(OAc)2], and [(p-cymene)Ru(OAc)2 afford the construction of binuclear metallocyclophanes [(Cp*Ir)2(m-POiP)2] (2), [(Cp*Rh)2(m-POiP)2 (3), and [((p-cymene)Ru)2(m-POiP)2] (4) in high yields. Crystal structures of 2, 3, and 4 illustrate binuclear metallocyclophanes constructed by cyclometallation by ortho-C–H activation and coordination of N-donor with metals which is confirmed by a single crystal X-ray diffraction (SC-XRD). Each metallocyclophanes shows unique packing structure by intermolecular hydrogen bonding; 2 and 3 shows 1D linear chain network, while the packing of 4 presents the 2D sheet.",

author = "Philjae Kang and Yonggoon Jeon and Younghun Kim and Choi, {Moon Gun}",

note = "Funding Information: We would like to acknowledge the financial support from the Korea Institute of Materials Science (Project No.:PNK‐5620). Publisher Copyright: {\textcopyright} 2018 Korean Chemical Society, Seoul & Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2018",

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AU - Kang, Philjae

AU - Jeon, Yonggoon

AU - Kim, Younghun

AU - Choi, Moon Gun

N1 - Funding Information: We would like to acknowledge the financial support from the Korea Institute of Materials Science (Project No.:PNK‐5620). Publisher Copyright: © 2018 Korean Chemical Society, Seoul & Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2018/9

Y1 - 2018/9

N2 - The multitopic ligand, 5-(pyridine-3-yloxy)isophthalic acid (m-POiPH2, 1), containing two different coordination sites of pyridine and isophthalic acid linked by the C–O–C bond, is prepared. The reaction of 1 with half sandwich complexes of [Cp*Rh(OAc)2] (Cp* = η5-C5Me5), [Cp*Ir(OAc)2], and [(p-cymene)Ru(OAc)2 afford the construction of binuclear metallocyclophanes [(Cp*Ir)2(m-POiP)2] (2), [(Cp*Rh)2(m-POiP)2 (3), and [((p-cymene)Ru)2(m-POiP)2] (4) in high yields. Crystal structures of 2, 3, and 4 illustrate binuclear metallocyclophanes constructed by cyclometallation by ortho-C–H activation and coordination of N-donor with metals which is confirmed by a single crystal X-ray diffraction (SC-XRD). Each metallocyclophanes shows unique packing structure by intermolecular hydrogen bonding; 2 and 3 shows 1D linear chain network, while the packing of 4 presents the 2D sheet.

AB - The multitopic ligand, 5-(pyridine-3-yloxy)isophthalic acid (m-POiPH2, 1), containing two different coordination sites of pyridine and isophthalic acid linked by the C–O–C bond, is prepared. The reaction of 1 with half sandwich complexes of [Cp*Rh(OAc)2] (Cp* = η5-C5Me5), [Cp*Ir(OAc)2], and [(p-cymene)Ru(OAc)2 afford the construction of binuclear metallocyclophanes [(Cp*Ir)2(m-POiP)2] (2), [(Cp*Rh)2(m-POiP)2 (3), and [((p-cymene)Ru)2(m-POiP)2] (4) in high yields. Crystal structures of 2, 3, and 4 illustrate binuclear metallocyclophanes constructed by cyclometallation by ortho-C–H activation and coordination of N-donor with metals which is confirmed by a single crystal X-ray diffraction (SC-XRD). Each metallocyclophanes shows unique packing structure by intermolecular hydrogen bonding; 2 and 3 shows 1D linear chain network, while the packing of 4 presents the 2D sheet.

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C–H Activation of the 5-(Pyridine-3-yloxy)isophthalic Acid to Construct Iridium, Rhodium, and Ruthenium Binuclear Metallocyclophanes

Abstract

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