Article

Palladium-catalyzed cascade process consisting of isocyanide insertion and benzylic C(sp3)-H activation: concise synthesis of indole derivatives.

Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan.
Organic Letters (impact factor: 5.86). 07/2012; 14(16):4270-3. DOI:10.1021/ol302035j pp.4270-3
Source: PubMed

ABSTRACT Synthesis of the indole skeleton was achieved using a Pd-catalyzed cascade process consisting of isocyanide insertion and benzylic C(sp(3))-H activation. It was found that slow addition of isocyanide is effective for reducing the amount of catalyst needed and Ad(2)P(n)Bu is a good ligand for C(sp(3))-H activation. The construction of the tetracyclic carbazole skeleton was also achieved by a Pd-catalyzed domino reaction incorporating alkyne insertion.

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Keywords

good ligand
 
isocyanide
 
isocyanide insertion
 
Pd-catalyzed cascade process
 
Pd-catalyzed domino reaction incorporating alkyne insertion
 
slow addition
 

Takeshi Nanjo