Abstract
Arylmanganese compounds were easily prepared via the direct oxidative addition of Rieke manganese to aryl bromides under mild conditions. The resulting organomanganese reagents undergo coupling reaction with acid chlorides to give the corresponding ketones in moderate yields.
Notes
In typical preparation, lithium (9.68 mmol), naphthalene (1.48 mmol), and anhydrous manganese iodide (4.71 mmol) under argon were stirred in freshly distilled THF (10 mL) for 1h at room temperature
1,2-Dibromoethane was used to consume the remaining active manganese in the reaction mixture because Mn∗ was active to additional electrophile to give a homocoupling product
a)“The Aldrich Library of NMR Spectra.” Edition 2, 1983, 1(2), 888A. “The Aldrich Library of IR Spectra.” Edition 2, 1983, 1(2), 60D. b) The Standard Sadtler Spectra; IR Grating 44201, 1H NMR 7302, c) “The Aldrich Library of NMR Spectra.” Edition 2, 1983, 1(2), 886A. “The Aldrich Library of IR Spectra.” Edition 2, 1983, 1(2), 59C. d) “The Aldrich Library of NMR Spectra.” Edition 2, 1983, 1(3), 1268A. “The Aldrich Library of IR Spectra.” Edition 2, 1983, 1(2), 888C. e) The Standard Sadtler Spectra; IR Grating 58746, 1H NMR 33805