Concepedia

A Tandem Heck-Carbocyclization/Suzuki-Coupling Approach to the Stereoselective Syntheses of Asymmetric 3,3-(Diarylmethylene)indolinones

Wing S. Cheung, Raymond J. Patch, Mark R. Player

The Journal of Organic Chemistry · 2005 · 126 citations · 7 references

DOI

Concepts

Abstract

[reaction: see text] An efficient and versatile method for stereoselective synthesis of (E)-3,3-(diarylmethylene)indolinones by a palladium-catalyzed tandem Heck-carbocyclization/Suzuki-coupling sequence is presented. Factors influencing yield and selectivity, namely catalyst, coordinating ligand, and solvent, are detailed.

References

7

The small molecule Hesperadin reveals a role for Aurora B in correcting kinetochore–microtubule attachment and in maintaining the spindle assembly checkpoint

Silke Hauf, Richard W. Cole, Sabrina LaTerra et al. · The Journal of Cell Biology · 2003 · 1.2K citations · Full text

Highly Active Palladium Catalysts for Suzuki Coupling Reactions

John P. Wolfe, Robert A. Singer, Bryant H. Yang et al. · Journal of the American Chemical Society · 1999 · 1.1K citations

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Highly Active, Air-Stable Palladium Catalysts for the C−C and C−S Bond-Forming Reactions of Vinyl and Aryl Chlorides:  Use of Commercially Available [(<i>t</i>-Bu)<sub>2</sub>P(OH)]<sub>2</sub>PdCl<sub>2</sub>, [(<i>t</i>-Bu)<sub>2</sub>P(OH)PdCl<sub>2</sub>]<sub>2</sub>, and [[(<i>t</i>-Bu)<sub>2</sub>PO···H···OP(<i>t</i>-Bu)<sub>2</sub>]PdCl]<sub>2</sub> as Catalysts

George Y. Li · The Journal of Organic Chemistry · 2002 · 196 citations

, , +15

Palladium−Imidazolium Carbene Catalyzed Aryl, Vinyl, and Alkyl Suzuki−Miyaura Cross Coupling

Merritt B. Andrus, Chun Song · Organic Letters · 2001 · 153 citations

Nonbasic, Room Temperature, Palladium-Catalyzed Coupling of Aryl and Alkenyl Iodides with Boronic Acids Mediated by Copper(I) Thiophene-2-carboxylate (CuTC)

Cécile Savarin, Lanny S. Liebeskind · Organic Letters · 2001 · 95 citations