141063-49-2Relevant academic research and scientific papers
Direct formation of highly functionalized allylic organocopper reagents from allylic chlorides and acetates
Stack, Douglas E.,Dawson, Bryan T.,Rieke, Reuben D.
, p. 5110 - 5116 (1992)
The direct formation of highly functionalized allylic. organocopper reagents has been carried out using a highly active form of zerovalent topper (Cu*). The cold-temperature reduction of CuCN-nLiX complexes by lithium naphthalenide in THF under an argon atmosphere produces the Cu* complex, which reacts rapidly with primary and secondary allyl chlorides at -100 °C with little homocoupling. Allyl, methallyl, and crotyl acetates also oxidatively add with Cu* at low temperatures to afford the corresponding organocopper reagent. Significantly, the allyl chlorides can contain a wide array of functional groups including ketones. α,β-unsaturated ketones, epoxides, alkyl acetates, esters, alkyl chlorides, nitriles, and carbamates. The cross-coupling of the highly functionalized allylic organocopper reagents with various electrophiles proceeds in excellent yields.
