Typical Reaction with Acid Chlorides to Form Ketones

Typical Reaction with Acid Chlorides to Form Ketones 

Lithium (71.2 mg, 10.3 mmol) and naphthalene (1.592 g, 12.42 mmol) in freshly distilled THF (10 ml) were stirred under argon until the Li was consumed ( 2 h). A solution of CulPBus (3.666 g, 9.333 mmol) and PBus (2.89 g, 14.3 mmol) in THF (5 ml) was added via cannula to the dark-green lithium naphthalenide solution at 0°C and the resultant reddish-black active copper solution was stirred for 20min. 1-Bromooctane (0.9032 g, 4.677 mmol) and GC internal standard -decane (0.1725 g, 1.212 mmol) in THF (5 ml) were added rapidly via cannula to the active copper solution at -78°C. The organocopper formation was typically complete within 20min at -78°C. 2-Cyclohexen-l-one (0.1875g, 

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