The cleavage of heteroaromatic endocyclic carbon-heteroatom bonds to assemble C-Si bonds is scarce. Here, we demonstrate an unprecedented dearomatization silylation of -arylindoles arising from reductive activation initiated by electron-rich silylboronic complexes to deliver silyl styrenes with perfect stereoselectivity.
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Ring-opening silylation of -arylindoles endocyclic C-N bond cleavage triggered by silylboranes.
Chem Commun (Camb)
October 2024
School of Chemistry and Material Science, Jiangsu Normal University, Xuzhou 221116, China.
The cleavage of heteroaromatic endocyclic carbon-heteroatom bonds to assemble C-Si bonds is scarce. Here, we demonstrate an unprecedented dearomatization silylation of -arylindoles arising from reductive activation initiated by electron-rich silylboronic complexes to deliver silyl styrenes with perfect stereoselectivity.
View Article and Find Full Text PDFSynthesis of Benzimidazo[2,1-]isoquinoline and Indolo[2,1-]isoquinoline Derivatives via Copper-Catalyzed Silylation/Methylation of 2-Arylindoles and 2-Arylbenzimidazoles.
J Org Chem
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State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, Gansu, China.
A one-pot method for the synthesis of silylsubstituted/methylsubstituted indolo[2,1-]isoquinolin-6(5)-ones and benzimidazo[2,1-]isoquinoline-6(5)-ones via copper(II)-initiated silylation/methylation of 2-arylindoles and 2-arylbenzimidazoles was developed. In this procedure, the C-Si bond and C-C bond were constructed by radical addition and cyclization. A series of 2-arylindole and 2-arylbenzimidazole derivatives were facilely transformed to indolo[2,1-]isoquinolines and benzimidazo[2,1-]isoquinolines in 39-83% yields.
View Article and Find Full Text PDFPalladium-catalyzed intramolecular coupling of 2-[(2-pyrrolyl)silyl]aryl triflates through 1,2-silicon migration.
J Am Chem Soc
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Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto University Katsura, Nishikyo-ku, Kyoto 615-8510, Japan.
Palladium-catalyzed intramolecular direct arylation of 2-[(2-pyrrolyl)silyl]aryl triflates gives 3,2'-silicon-bridged 2-arylindoles and -pyrroles in good to high yields. The reaction proceeds through cleavage of C-OTf, C-Si, and C-H bonds to result in the formation of C-C and C-Si bonds. Various kinds of functional groups such as OMe, CN, Cl, F, and SiMe(3) tolerated the conditions.
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