Methylenation of Aldehydes: Transition Metal Catalyzed Formation of Salt-Free Phosphorus Ylides
- 3 August 2001
- journal article
- Published by Wiley in Angewandte Chemie International Edition in English
- Vol. 40 (15) , 2887-2890
- https://doi.org/10.1002/1521-3773(20010803)40:15<2887::aid-anie2887>3.0.co;2-q
Abstract
A variety of terminal alkenes are produced in excellent yields by the rhodium(I)-catalyzed methylenation of aldehydes using TMSCHN2 and PPh3 [Eq. (1)]. These mild reaction conditions allowed the conversion of enolizable substrates and the chemoselective methylenation of aldehydes over ketones. TMS=trimethylsilyl.Keywords
This publication has 37 references indexed in Scilit:
- Olefinmetathese und mehrAngewandte Chemie, 2000
- Stereocontrolled Synthesis of the JKLM Ring Fragment of CiguatoxinThe Journal of Organic Chemistry, 1999
- Stereoselective Isoquinoline Alkaloid Synthesis with New DiselenidesSynthesis, 1998
- A New Family of Carbenerhodium(I) Complexes: Ligand Variation as The Key to SuccessChemistry – A European Journal, 1997
- Multiple Bonds between Main-Group Elements and Transition Metals. 135. Oxorhenium(V) Catalysts for the Olefination of AldehydesOrganometallics, 1994
- Carbenrhodium‐Komplexe mit Diaryl‐ und Alkyl(aryl)carbenen als Liganden: Das fehlende Glied in der Reihe der Doppelbindungssysteme trans‐[RhCl{C(C)nRR′}(L)2], n = 0, 1 und 2Angewandte Chemie, 1993
- Chiral Preparation of (R)- and (S)-3-(Benzyloxy)-4,4-dimethyl-1-penteneSynthesis, 1993
- Methyltrioxorhenium als Katalysator einer neuen Aldehyd‐OlefinierungAngewandte Chemie, 1991
- Synthesis and reactions of Ru(CH2)Cl(NO)(PPh3)2, a stable terminal methylene complex and the crystal structure of Ru(CH2PPh3)(η2-C2F4)Cl(NO)(PPh3)J. Chem. Soc., Dalton Trans., 1991
- New methods and reagents in organic synthesis. 14. A simple efficient preparation of methyl esters with trimethylsilyldiazomethane (TMSCHN2) and its application to gas chromatographic analysis of fatty acids.CHEMICAL & PHARMACEUTICAL BULLETIN, 1981