Me2Zn-Mediated Addition of Acetylenes to Aldehydes and Ketones
- 7 June 2005
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 70 (14) , 5733-5736
- https://doi.org/10.1021/jo050115r
Abstract
Contrary to expectations, commercially available 2 M Me2Zn in toluene is able to promote the addition of phenylacetylene to aldehydes and ketones. This reactivity is determined by a new, unprecedented mechanism, which involves activation of the zinc reagent via coordination with carbonyl substrates that behave “ligand like”. Broad scope, high tolerance to functional groups, and a simple procedure make this new method highly interesting for the synthetic chemist.Keywords
This publication has 36 references indexed in Scilit:
- New Insights into the Stereoselectivity of the Aryl Zinc Addition to AldehydesJournal of the American Chemical Society, 2005
- Phenyl versus Ethyl Transfer in the Addition of Organozinc Reagents to Aldehydes: A Theoretical StudyAngewandte Chemie International Edition in English, 2003
- Catalytic Alkynylation of Ketones and Aldehydes Using Quaternary Ammonium Hydroxide BaseThe Journal of Organic Chemistry, 2003
- Modeling the Stereoselectivity of the β-Amino Alcohol-Promoted Addition of Dialkylzinc to AldehydesJournal of the American Chemical Society, 2003
- Total Synthesis of the Epidermal Growth Factor Inhibitor (−)-Reveromycin BThe Journal of Organic Chemistry, 2001
- Solvent-Free Addition of Ethynylbenzene to KetonesBulletin of the Chemical Society of Japan, 2001
- First Total Synthesis of Aspinolide B, a New Pentaketide Produced by Aspergillus ochraceusThe Journal of Organic Chemistry, 2000
- Enantioselective Alkynylation of Aromatic Aldehydes Catalyzed by Readily Available Chiral Amino Alcohol-Based LigandsSynthesis, 1999
- 13C CP/MAS NMR study of a phenyl group rotation in the solid state using T1ρ, lineshape and 2D EXSY measurementsMagnetic Resonance in Chemistry, 1994
- Zur Chemie acetylenischer Titan‐ VerbindungenEuropean Journal of Inorganic Chemistry, 1987