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Article: Primary and secondary phosphine complexes of iron porphyrins and ruthenium phthalocyanine: Synthesis, structure, and P-H bond functionalization

TitlePrimary and secondary phosphine complexes of iron porphyrins and ruthenium phthalocyanine: Synthesis, structure, and P-H bond functionalization
Authors
Issue Date2008
PublisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/ic
Citation
Inorganic Chemistry, 2008, v. 47 n. 20, p. 9166-9181 How to Cite?
AbstractReduction of [Fe III(Por)Cl] (Por = porphyrinato dianion) with Na 2S 2O 4 followed by reaction with excess PH 2Ph, PH 2Ad, or PHPh 2 afforded [Fe II(F 20-TPP)(PH 2Ph) 2] (1a), [Fe II(F 20-TPP)(PH 2Ad) 2] (1b), [Fe II(F 20-TPP)(PHPh 2) 2] (2a), and [Fe II(2,6-Cl 2TPP)(PHPh 2) 2] (2b). Reaction of [Ru II(Pc)(DMSO) 2] (Pc = phthatocyaninato dianion) with PH 2Ph or PHPh 2 gave [Ru II(Pc) (PH 2Ph) 2] (3a) and [Ru II(Pc)(PHPh 2) 2] (4). [Ru II(Pc)(PH 2Ad) 2] (3b) and [Ru II(Pc)(PH 2Bu t) 2] (3c) were isolated by treating a mixture of [Ru II(Pc)(DMSO) 2] and O=PCl 2Ad or PCl 2Bu t with LiAlH 4. Hydrophosphination of CH 2=CHR (R = CO 2Et, CN) with [Ru II(F 20-TPP)(PH 2Ph) 2] or [Ru II(F 20-TPP)(PHPh 2) 2] in the presence of tBuOK led to the isolation of [Ru II(F 20-TPP) (P(CH 2CH 2R) 2Ph) 2] (R = CO 2Et, 5a; CN, 5b) and [Ru II(F 20-TPP)(P(CH 2CH 2R)Ph 2) 2] (R = CO 2Et, 6a; CN, 6b). Similar reaction of 3a with CH 2=CHCN or Mel gave [Ru II(Pc)(P(CH 2CH 2CN) 2Ph) 2] (7) or [Ru II(Pc)(PMe 2Ph) 2] (8). The reactions of 4 with CH 2=CHR (R = CO 2Et, CN, C(O)Me, P(O)(OEt) 2, S(O) 2Ph), CH 2=C(Me)CO 2Me, CH(CO 2Me)=CHCO 2Me, Mel, BnCl, and RBr (R = nBu, CH 2=CHCH 2, MeC≡CCH 2, HC≡CCH 2) in the presence of tBuOK afforded [Ru II(Pc)(P(CH 2CH 2R)Ph 2) 2] (R = CO 2Et, 9a; CN, 9b; C(O)Me, 9c; P(O)(OEt) 2, 9d; S(O) 2Ph, 9e), [Ru II(Pc)(P(CH 2CH(Me)CO 2Me)Ph 2) 2] (9f), [RU II(PC) (P(CH(CO 2Me)CH 2CO 2Me)Ph 2) 2] (9g), and [Ru II(Pc)(PRPh 2) 2] (R = Me, 10a; Bu n, 10b; Bn, 10c; CH 2CH=CH 2, 10d; CH 2C≡CMe, 10e; CH=C=CH 2, 10f). X-ray crystal structure determinations revealed Fe-P distances of 2.2597(9) (1a) and 2.309(2) Å(2b·2CH 2Cl 2) and Ru-P distances of 2.3707(13) (3b), 2.373(2) (3c), 2.3478(11) (4), and 2.3754(10) Å(5b·2CH 2Cl 2). Both the crystal structures of 3b and 4 feature intermolecular C-H ⋯ π interactions, which link the molecules into 3D and 2D networks, respectively. © 2008 American Chemical Society.
Persistent Identifierhttp://hdl.handle.net/10722/58388
ISSN
2015 Impact Factor: 4.82
2015 SCImago Journal Rankings: 1.873
ISI Accession Number ID
Funding AgencyGrant Number
The University of Hong Kong
Hong Kong Research Grants CouncilHKU7026/04P
University Grants Committee of the Hong Kong SAR of ChinaAoE/P-10/01
Funding Information:

This work was supported by The University of Hong Kong (Seed Funding for Basic Research), Hong Kong Research Grants Council (HKU7026/04P), and the University Grants Committee of the Hong Kong SAR of China (Area of Excellence Scheme, AoE/P-10/01).

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DC FieldValueLanguage
dc.contributor.authorHuang, JSen_HK
dc.contributor.authorYu, GAen_HK
dc.contributor.authorXie, Jen_HK
dc.contributor.authorWong, KMen_HK
dc.contributor.authorZhu, Nen_HK
dc.contributor.authorChe, CMen_HK
dc.date.accessioned2010-05-31T03:29:25Z-
dc.date.available2010-05-31T03:29:25Z-
dc.date.issued2008en_HK
dc.identifier.citationInorganic Chemistry, 2008, v. 47 n. 20, p. 9166-9181en_HK
dc.identifier.issn0020-1669en_HK
dc.identifier.urihttp://hdl.handle.net/10722/58388-
dc.description.abstractReduction of [Fe III(Por)Cl] (Por = porphyrinato dianion) with Na 2S 2O 4 followed by reaction with excess PH 2Ph, PH 2Ad, or PHPh 2 afforded [Fe II(F 20-TPP)(PH 2Ph) 2] (1a), [Fe II(F 20-TPP)(PH 2Ad) 2] (1b), [Fe II(F 20-TPP)(PHPh 2) 2] (2a), and [Fe II(2,6-Cl 2TPP)(PHPh 2) 2] (2b). Reaction of [Ru II(Pc)(DMSO) 2] (Pc = phthatocyaninato dianion) with PH 2Ph or PHPh 2 gave [Ru II(Pc) (PH 2Ph) 2] (3a) and [Ru II(Pc)(PHPh 2) 2] (4). [Ru II(Pc)(PH 2Ad) 2] (3b) and [Ru II(Pc)(PH 2Bu t) 2] (3c) were isolated by treating a mixture of [Ru II(Pc)(DMSO) 2] and O=PCl 2Ad or PCl 2Bu t with LiAlH 4. Hydrophosphination of CH 2=CHR (R = CO 2Et, CN) with [Ru II(F 20-TPP)(PH 2Ph) 2] or [Ru II(F 20-TPP)(PHPh 2) 2] in the presence of tBuOK led to the isolation of [Ru II(F 20-TPP) (P(CH 2CH 2R) 2Ph) 2] (R = CO 2Et, 5a; CN, 5b) and [Ru II(F 20-TPP)(P(CH 2CH 2R)Ph 2) 2] (R = CO 2Et, 6a; CN, 6b). Similar reaction of 3a with CH 2=CHCN or Mel gave [Ru II(Pc)(P(CH 2CH 2CN) 2Ph) 2] (7) or [Ru II(Pc)(PMe 2Ph) 2] (8). The reactions of 4 with CH 2=CHR (R = CO 2Et, CN, C(O)Me, P(O)(OEt) 2, S(O) 2Ph), CH 2=C(Me)CO 2Me, CH(CO 2Me)=CHCO 2Me, Mel, BnCl, and RBr (R = nBu, CH 2=CHCH 2, MeC≡CCH 2, HC≡CCH 2) in the presence of tBuOK afforded [Ru II(Pc)(P(CH 2CH 2R)Ph 2) 2] (R = CO 2Et, 9a; CN, 9b; C(O)Me, 9c; P(O)(OEt) 2, 9d; S(O) 2Ph, 9e), [Ru II(Pc)(P(CH 2CH(Me)CO 2Me)Ph 2) 2] (9f), [RU II(PC) (P(CH(CO 2Me)CH 2CO 2Me)Ph 2) 2] (9g), and [Ru II(Pc)(PRPh 2) 2] (R = Me, 10a; Bu n, 10b; Bn, 10c; CH 2CH=CH 2, 10d; CH 2C≡CMe, 10e; CH=C=CH 2, 10f). X-ray crystal structure determinations revealed Fe-P distances of 2.2597(9) (1a) and 2.309(2) Å(2b·2CH 2Cl 2) and Ru-P distances of 2.3707(13) (3b), 2.373(2) (3c), 2.3478(11) (4), and 2.3754(10) Å(5b·2CH 2Cl 2). Both the crystal structures of 3b and 4 feature intermolecular C-H ⋯ π interactions, which link the molecules into 3D and 2D networks, respectively. © 2008 American Chemical Society.en_HK
dc.languageengen_HK
dc.publisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/icen_HK
dc.relation.ispartofInorganic Chemistryen_HK
dc.titlePrimary and secondary phosphine complexes of iron porphyrins and ruthenium phthalocyanine: Synthesis, structure, and P-H bond functionalizationen_HK
dc.typeArticleen_HK
dc.identifier.openurlhttp://library.hku.hk:4550/resserv?sid=HKU:IR&issn=0020-1669&volume=47&spage=9166&epage=9181&date=2008&atitle=Primary+and+Secondary+Phosphine+Complexes+of+Iron+Porphyrins+and+Ruthenium+Phthalocyanine:+Synthesis,+Structure,+and+P-H+Bond+Functionalizationen_HK
dc.identifier.emailHuang, JS: jshuang@hku.hken_HK
dc.identifier.emailZhu, N: nzhu@hkucc.hku.hken_HK
dc.identifier.emailChe, CM: cmche@hku.hken_HK
dc.identifier.authorityHuang, JS=rp00709en_HK
dc.identifier.authorityZhu, N=rp00845en_HK
dc.identifier.authorityChe, CM=rp00670en_HK
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1021/ic800484ken_HK
dc.identifier.pmid18800835-
dc.identifier.scopuseid_2-s2.0-55249126872en_HK
dc.identifier.hkuros147871en_HK
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-55249126872&selection=ref&src=s&origin=recordpageen_HK
dc.identifier.volume47en_HK
dc.identifier.issue20en_HK
dc.identifier.spage9166en_HK
dc.identifier.epage9181en_HK
dc.identifier.eissn1520-510X-
dc.identifier.isiWOS:000259988600013-
dc.publisher.placeUnited Statesen_HK
dc.relation.projectInstitute of molecular technology for drug discovery and synthesis-
dc.identifier.scopusauthoridHuang, JS=7407192639en_HK
dc.identifier.scopusauthoridYu, GA=8252045600en_HK
dc.identifier.scopusauthoridXie, J=55478195600en_HK
dc.identifier.scopusauthoridWong, KM=25633413900en_HK
dc.identifier.scopusauthoridZhu, N=7201449530en_HK
dc.identifier.scopusauthoridChe, CM=7102442791en_HK

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