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Oxidative demetalation of Fischer alkoxy carbene complexes with stoichiometric pyridine N-oxide and NaBH4-promoted demetalation of Fischer iminocarbene complexes with sulfur and selenium
Zheng, Zhaoyan; Chen, Jinzhu; Yu, Zhengkun; Han, Xiuwen; Yu ZK(余正坤); Yu ZK(余正坤)
KeywordFischer Carbene Pyridine N-oxide Iminocarbene Sulfur Selenium
Source PublicationJOURNAL OF ORGANOMETALLIC CHEMISTRY
2006-08-15
DOI10.1016/j.jorganchem.2006.05.021
Volume691Issue:17Pages:3679-3692
Indexed BySCI ; IC ; CCR
SubtypeArticle
Department2,5
Funding Project203,502
Contribution Rank1;1
WOS HeadingsScience & Technology ; Physical Sciences
WOS SubjectChemistry, Inorganic & Nuclear ; Chemistry, Organic
WOS Research AreaChemistry
WOS KeywordTRANSITION-METAL-COMPLEXES ; DIELS-ALDER REACTIONS ; TUNGSTEN PENTACARBONYL GROUPS ; LEWIS ACID CATALYSIS ; ASYMMETRIC-SYNTHESIS ; ORGANIC SYNTHESES ; ALKENYLCARBENE COMPLEXES ; SELECTIVE ISOMERIZATION ; PHOTOCHEMICAL-REACTIONS ; C BONDS
AbstractOxidation of Fischer alkoxy carbene complexes were systematically investigated with stoichiometric pyridine N-oxide (PNO) under mild conditions, forming ester products in good to excellent yields from the corresponding monocarbene complexes. Fischer alkoxy biscarbene complexes efficiently underwent stepwise oxidative demetalation under controlled conditions, resulting in ester-monocarbene and diester products, respectively. This oxidation protocol has demonstrated a generally efficient method to oxidize Fischer alkoxy carbene complexes under mild conditions, providing a new route to novel monocarbene complexes from Fischer biscarbene complexes. In the presence of NaBH4, reactions of Fischer iminocarbene complexes with elemental sulfur or selenium in ethanol at ambient temperature regioselectively afforded thione or selone complexes by insertion of a sulfur or selenium atom into the M=C bonds in Fischer carbene complexes, and metal-free selone was also obtained. The molecular structures of the iminocarbene complexes and selone derivatives were confirmed by X-ray crystallographic study. The NaBH4-promoted demetalation protocol suggests a potential new route to demetalate Fischer aminocarbene complexes. (c) 2006 Elsevier B.V. All rights reserved.
Language英语
URL查看原文
WOS IDWOS:000239833100017
Citation statistics
Cited Times:15[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://cas-ir.dicp.ac.cn/handle/321008/97203
Collection中国科学院大连化学物理研究所
Corresponding AuthorYu ZK(余正坤); Yu ZK(余正坤)
AffiliationChinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Catalysis, Dalian 116023, Liaoning, Peoples R China
Recommended Citation
GB/T 7714
Zheng, Zhaoyan,Chen, Jinzhu,Yu, Zhengkun,et al. Oxidative demetalation of Fischer alkoxy carbene complexes with stoichiometric pyridine N-oxide and NaBH4-promoted demetalation of Fischer iminocarbene complexes with sulfur and selenium[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY,2006,691(17):3679-3692.
APA Zheng, Zhaoyan,Chen, Jinzhu,Yu, Zhengkun,Han, Xiuwen,余正坤,&余正坤.(2006).Oxidative demetalation of Fischer alkoxy carbene complexes with stoichiometric pyridine N-oxide and NaBH4-promoted demetalation of Fischer iminocarbene complexes with sulfur and selenium.JOURNAL OF ORGANOMETALLIC CHEMISTRY,691(17),3679-3692.
MLA Zheng, Zhaoyan,et al."Oxidative demetalation of Fischer alkoxy carbene complexes with stoichiometric pyridine N-oxide and NaBH4-promoted demetalation of Fischer iminocarbene complexes with sulfur and selenium".JOURNAL OF ORGANOMETALLIC CHEMISTRY 691.17(2006):3679-3692.
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