Palladium-Catalyzed Synthesis of Benzophenanthrosilines by C-H/C-H Coupling through 1,4-Palladium Migration/Alkene Stereoisomerization.

Angew Chem Int Ed Engl

Division of Chemistry, Department of Materials Engineering Science, Graduate School of Engineering Science, Osaka University, Toyonaka, Osaka, 560-8531, Japan.

Published: May 2020

AI Article Synopsis

  • - A novel method for creating 8H-benzo[e]phenanthro[1,10-bc]silines has been established, using 2-((2-(arylethynyl)aryl)silyl)aryl triflates and palladium as a catalyst.
  • - Researchers studied the reaction process and suggested a mechanism involving C-H coupling aided by a unique 1,4-palladium migration, which also leads to the rearrangement of alkene stereoisomers.
  • - This development highlights advancements in synthetic chemistry and the application of palladium catalysis in complex molecule formation.

Article Abstract

A new and efficient synthesis of 8H-benzo[e]phenanthro[1,10-bc]silines from 2-((2-(arylethynyl)aryl)silyl)aryl triflates under palladium catalysis has been developed. The reaction mechanism was experimentally investigated and a catalytic cycle involving C-H/C-H coupling through a new mode of 1,4-palladium migration with concomitant alkene stereoisomerization is proposed.

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http://dx.doi.org/10.1002/anie.202000217DOI Listing

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