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Synfacts 2009(9): 0987-0987
DOI: 10.1055/s-0029-1217639
DOI: 10.1055/s-0029-1217639
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag
Stuttgart ˙ New York
Ir-Catalyzed Cross-Coupling of Styrene Derivatives with Allylic Carbonates
Contributor(s):Mark Lautens, Jacki KitchingH. He, W.-B. Liu, L.-X. Dai, S.-L. You*
Shanghai Institute of Organic Chemistry, P. R. of China
Ir-Catalyzed Cross-Coupling of Styrene Derivatives with Allylic Carbonates: Free Amine Assisted Vinyl C-H Bond Activation
J. Am. Chem. Soc. 2009, 131, 8346-8347
Shanghai Institute of Organic Chemistry, P. R. of China
Ir-Catalyzed Cross-Coupling of Styrene Derivatives with Allylic Carbonates: Free Amine Assisted Vinyl C-H Bond Activation
J. Am. Chem. Soc. 2009, 131, 8346-8347
Further Information
Publication History
Publication Date:
21 August 2009 (online)
Key words
styrenes - allylic carbonates - iridium
Significance
The iridium-catalyzed cross-coupling of o-amino-styrene derivatives with allylic carbonates is described. The procedure affords skipped Z,E-dienes with the exclusive formation of a cis double bond.
Comment
This protocol has a broad substrate scope and affords the desired products in good yield. It is noteworthy that less of the isomerized byproducts were observed in reactions involving aliphatic allylic carbonates. The proposed mechanism involves an iridium-catalyzed amine-assisted vinyl C-H bond activation process, a notion that is supported by deuterium labeling experiments.