New Efficient Nickel-Catalyzed Cross-Coupling Reaction between Two Csp3Centers
- 29 April 1999
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 64 (10) , 3544-3553
- https://doi.org/10.1021/jo982317b
Abstract
The presence of a remote unsaturation (double bond, carbonyl group, cyano group) in an alkyl halide facilitates its cross-coupling reaction with various diorganozincs in the presence of Ni(acac)2 (7.5−10 mol % in THF/NMP mixtures). These results were used to develop a new general cross-coupling reaction between functionalized diorganozincs and alkyl iodides using m- or p-trifluoromethylstyrene as a reaction promotor and Ni(acac)2 as a catalyst (7.5−10 mol %; −35 °C, 5−10 h) leading to a broad range of polyfunctional cross-coupling products.Keywords
This publication has 35 references indexed in Scilit:
- Catalytic Asymmetric Addition of Polyfunctional Dialkylzincs to .beta.-Stannylated and .beta.-Silylated Unsaturated AldehydesThe Journal of Organic Chemistry, 1994
- Synthesis of Long Chain ω-AralkylbromidesSynthetic Communications, 1994
- Lewis acid promoted, cobalt-catalyzed, and phase-transfer-catalyzed carbonylation of iodo arenes and iodo alkanesOrganometallics, 1990
- Cycloaddition reactions of a bisisobenzofuran leading to linear polyacenequinones and a quadruply bridged cyclophaneThe Journal of Organic Chemistry, 1987
- Functionalized ethylene oligomers as phase-transfer catalystsThe Journal of Organic Chemistry, 1985
- Reversible formal alkene insertion into a chelated platinum-alkyl bondJournal of the American Chemical Society, 1984
- Synthesen von trail‐Pheromonen der Pharaoameise (Monomorium pharaonis(L.))Journal für Praktische Chemie, 1980
- Studies in macrolide synthesis; control of remote stereochemistry by sulfenic acid cyclization and 2,3-sigmatropic ring expansionThe Journal of Organic Chemistry, 1979
- High-spin-low-spin equilibrium of manganocene and dimethylmanganoceneJournal of the American Chemical Society, 1974
- Mechanism of bimolecular nucleophilic substitution in .beta.-halo ketones and related compoundsThe Journal of Organic Chemistry, 1972