File Download
There are no files associated with this item.
Links for fulltext
(May Require Subscription)
- Publisher Website: 10.1021/ja020391c
- Scopus: eid_2-s2.0-0037032218
- PMID: 12405847
- WOS: WOS:000178966700047
- Find via
Supplementary
- Citations:
- Appears in Collections:
Article: Remarkably stable iron porphyrins bearing nonheteroatom-stabilized carbene or (alkoxycarbonyl)carbenes: Isolation, X-ray crystal structures, and carbon atom transfer reactions with hydrocarbons
Title | Remarkably stable iron porphyrins bearing nonheteroatom-stabilized carbene or (alkoxycarbonyl)carbenes: Isolation, X-ray crystal structures, and carbon atom transfer reactions with hydrocarbons |
---|---|
Authors | |
Issue Date | 2002 |
Publisher | American Chemical Society. The Journal's web site is located at http://pubs.acs.org/journals/jacsat/index.html |
Citation | Journal Of The American Chemical Society, 2002, v. 124 n. 44, p. 13185-13193 How to Cite? |
Abstract | Reactions of [Fe(TPFPP)] (TPFPP = meso-tetrakis(pentafluorophenyl)porphyrinato dianion) with diazo compounds N 2C(Ph)R (R = Ph, CO 2Et, CO 2CH 2CH=CH 2) afforded [Fe(TPFPP)(C(Ph)R)] (R = Ph (1), CO 2Et (2), CO 2CH 2CH=CH 2 (3)) in 65-70% yields. Treatment of 1 with N-methylimidazole (Melm) gave the adduct [Fe(TPFPP)(CPh 2)(Melm)] (4) in 65% yield. These new iron porphyrin carbene complexes were characterized by NMR and UV-vis spectroscopy, mass spectrometry, and elemental analyses. X-ray crystal structure determinations of 1·0.5C 6H 6·0.5CH 2Cl 2 and 4 reveal Fe=CPh 2 bond lengths of 1.767(3) (1) and 1.827(5) Å (4), together with large ruffling distortions of the TPFPP macrocycle. Complexes 2 and 4 are reactive toward styrene, affording the corresponding cyclopropanes in 82 and 53% yields, respectively. Complex 1 is an active catalyst for both intermolecular cyclopropanation of styrenes with ethyl diazoacetate and intramolecular cyclopropanation of allylic diazoacetates. Reactions of 2 and 4 with cyclohexene or cumene produced allylic or benzylic C-H insertion products in up to 83% yield. |
Persistent Identifier | http://hdl.handle.net/10722/69891 |
ISSN | 2023 Impact Factor: 14.4 2023 SCImago Journal Rankings: 5.489 |
ISI Accession Number ID | |
References |
DC Field | Value | Language |
---|---|---|
dc.contributor.author | Li, Y | en_HK |
dc.contributor.author | Huang, JS | en_HK |
dc.contributor.author | Zhou, ZY | en_HK |
dc.contributor.author | Che, CM | en_HK |
dc.contributor.author | You, XZ | en_HK |
dc.date.accessioned | 2010-09-06T06:17:47Z | - |
dc.date.available | 2010-09-06T06:17:47Z | - |
dc.date.issued | 2002 | en_HK |
dc.identifier.citation | Journal Of The American Chemical Society, 2002, v. 124 n. 44, p. 13185-13193 | en_HK |
dc.identifier.issn | 0002-7863 | en_HK |
dc.identifier.uri | http://hdl.handle.net/10722/69891 | - |
dc.description.abstract | Reactions of [Fe(TPFPP)] (TPFPP = meso-tetrakis(pentafluorophenyl)porphyrinato dianion) with diazo compounds N 2C(Ph)R (R = Ph, CO 2Et, CO 2CH 2CH=CH 2) afforded [Fe(TPFPP)(C(Ph)R)] (R = Ph (1), CO 2Et (2), CO 2CH 2CH=CH 2 (3)) in 65-70% yields. Treatment of 1 with N-methylimidazole (Melm) gave the adduct [Fe(TPFPP)(CPh 2)(Melm)] (4) in 65% yield. These new iron porphyrin carbene complexes were characterized by NMR and UV-vis spectroscopy, mass spectrometry, and elemental analyses. X-ray crystal structure determinations of 1·0.5C 6H 6·0.5CH 2Cl 2 and 4 reveal Fe=CPh 2 bond lengths of 1.767(3) (1) and 1.827(5) Å (4), together with large ruffling distortions of the TPFPP macrocycle. Complexes 2 and 4 are reactive toward styrene, affording the corresponding cyclopropanes in 82 and 53% yields, respectively. Complex 1 is an active catalyst for both intermolecular cyclopropanation of styrenes with ethyl diazoacetate and intramolecular cyclopropanation of allylic diazoacetates. Reactions of 2 and 4 with cyclohexene or cumene produced allylic or benzylic C-H insertion products in up to 83% yield. | en_HK |
dc.language | eng | en_HK |
dc.publisher | American Chemical Society. The Journal's web site is located at http://pubs.acs.org/journals/jacsat/index.html | en_HK |
dc.relation.ispartof | Journal of the American Chemical Society | en_HK |
dc.title | Remarkably stable iron porphyrins bearing nonheteroatom-stabilized carbene or (alkoxycarbonyl)carbenes: Isolation, X-ray crystal structures, and carbon atom transfer reactions with hydrocarbons | en_HK |
dc.type | Article | en_HK |
dc.identifier.openurl | http://library.hku.hk:4550/resserv?sid=HKU:IR&issn=0002-7863&volume=124&issue=44&spage=13185&epage=13193&date=2002&atitle=Remarkably+stable+iron+porphyrins+bearing+nonheteroatom-stabilized+carbene+or+(alkoxycarbonyl)carbenes;++Isolation,+X-ray+crystal+structures,+and+carbon+atom+transfer+reactions+with+hydrocarbons | en_HK |
dc.identifier.email | Huang, JS:jshuang@hkucc.hku.hk | en_HK |
dc.identifier.email | Che, CM:cmche@hku.hk | en_HK |
dc.identifier.authority | Huang, JS=rp00709 | en_HK |
dc.identifier.authority | Che, CM=rp00670 | en_HK |
dc.description.nature | link_to_subscribed_fulltext | - |
dc.identifier.doi | 10.1021/ja020391c | en_HK |
dc.identifier.pmid | 12405847 | - |
dc.identifier.scopus | eid_2-s2.0-0037032218 | en_HK |
dc.identifier.hkuros | 81067 | en_HK |
dc.relation.references | http://www.scopus.com/mlt/select.url?eid=2-s2.0-0037032218&selection=ref&src=s&origin=recordpage | en_HK |
dc.identifier.volume | 124 | en_HK |
dc.identifier.issue | 44 | en_HK |
dc.identifier.spage | 13185 | en_HK |
dc.identifier.epage | 13193 | en_HK |
dc.identifier.isi | WOS:000178966700047 | - |
dc.publisher.place | United States | en_HK |
dc.identifier.scopusauthorid | Li, Y=35187394200 | en_HK |
dc.identifier.scopusauthorid | Huang, JS=7407192639 | en_HK |
dc.identifier.scopusauthorid | Zhou, ZY=35081598000 | en_HK |
dc.identifier.scopusauthorid | Che, CM=7102442791 | en_HK |
dc.identifier.scopusauthorid | You, XZ=36072101800 | en_HK |
dc.identifier.issnl | 0002-7863 | - |