A method for the oxidative coupling of arylsilanes with nitrogen nucleophiles is reported. This method occurs with a broad range of heptamethyltrisiloxylarenes and nitrogen nucleophiles, proceeds with the arylsilane as limiting reagent, and does not require a fluoride activator with electron-poor arylsilanes. The combination of this method with C-H silylation generates arylamines from unactivated arenes with site selectivity controlled by steric effects. This combination of steps gives direct access to many compounds that cannot be accessed via alternative C-H functionalization methods, including direct C-H amination or the combination of C-H borylation and amination.
A method for the oxidative coupling of arylsilanes with n class="Chemical">nitrogen nucleophiles is reported. This method occurs with a broad range of heptamethyltrisiloxylarenes and nitrogen nucleophiles, proceeds with the arylsilane as limiting reagent, and does not require a fluoride activator with electron-poor arylsilanes. The combination of this method with C-H silylation generates arylamines from unactivated arenes with site selectivity controlled by steric effects. This combination of steps gives direct access to many compounds that cannot be accessed via alternative C-H functionalization methods, including direct C-H amination or the combination of C-H borylation and amination.
Authors: Wei Wang; Pratik Devasthale; Dennis Farrelly; Liqun Gu; Thomas Harrity; Michael Cap; Cuixia Chu; Lori Kunselman; Nathan Morgan; Randy Ponticiello; Rachel Zebo; Litao Zhang; Kenneth Locke; Jonathan Lippy; Kevin O'Malley; Vinayak Hosagrahara; Lisa Zhang; Pathanjali Kadiyala; Chiehying Chang; Jodi Muckelbauer; Arthur M Doweyko; Robert Zahler; Denis Ryono; Narayanan Hariharan; Peter T W Cheng Journal: Bioorg Med Chem Lett Date: 2008-02-07 Impact factor: 2.823
Authors: Julien C Vantourout; Robert P Law; Albert Isidro-Llobet; Stephen J Atkinson; Allan J B Watson Journal: J Org Chem Date: 2016-04-18 Impact factor: 4.354