Journal article
Functionalized spiro- and fused-ring heterocycles via oxidative demetalation of cyclohexadienyl ruthenium complexes
Journal of organic chemistry, Vol.69(4), pp.1161-1168
2004
DOI: 10.1021/jo035058l
PMID: 14961665
Abstract
Electron-rich alkoxy- and chloro-substituted azaspirocyclic cyclohexadienyl Ru(II) complexes have been converted to either azaspiro[4.5]decane derivatives or functionalized tetrahydroisoquinolines by treatment with suitable oxidizing agents. Copper(II) chloride was found to provide demetalated products in high yield relative to the other oxidants examined (FeCl3, DDQ, CAN, [Cp2Fe][PF6], phenyliodine diacetate, IBX). In certain instances, the efficiency of oxidative demetalation was enhanced by the inclusion of chloride ion additives in the reaction. Pyridinium dichromate (PDC) was also found to effect the demetalation of a wide range of cyclohexadienyl Ru complexes; however, isolated yields of metal-free products were exceedingly low. The cyclohexadienyl ruthenium complexes used in this study were prepared from (arene)Ru(II) precursors; thus, the isolation of alicyclic cyclohexadienone derivatives upon demetalation constitutes completion of a Ru-mediated dearomatization process.
Details
- Title: Subtitle
- Functionalized spiro- and fused-ring heterocycles via oxidative demetalation of cyclohexadienyl ruthenium complexes
- Creators
- F. Christopher Pigge - Department of Chemistry and Biochemistry, University of Missouri-St. Louis, 8001 Natural Bridge Road, St. Louis, Missouri 63121-4499, United StatesJohn J Coniglio - Department of Chemistry and Biochemistry, University of Missouri-St. Louis, 8001 Natural Bridge Road, St. Louis, Missouri 63121-4499, United StatesNigam P Rath - Department of Chemistry and Biochemistry, University of Missouri-St. Louis, 8001 Natural Bridge Road, St. Louis, Missouri 63121-4499, United States
- Resource Type
- Journal article
- Publication Details
- Journal of organic chemistry, Vol.69(4), pp.1161-1168
- DOI
- 10.1021/jo035058l
- PMID
- 14961665
- NLM abbreviation
- J Org Chem
- ISSN
- 0022-3263
- eISSN
- 1520-6904
- Publisher
- American Chemical Society
- Language
- English
- Date published
- 2004
- Academic Unit
- Radiology; Chemistry
- Record Identifier
- 9984216591402771
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