Direct formation of highly functionalized allylic organocopper reagents from allylic chlorides and acetates

DE Stack, BT Dawson, RD Rieke

Index: Stack, Douglas E.; Dawson, Bryan T.; Rieke, Reuben D. Journal of the American Chemical Society, 1992 , vol. 114, # 13 p. 5110 - 5116

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Citation Number: 25

Abstract

Abstract: The direct formation of highly functionalized allylic organocopper reagents has been carried out using a highly active form of zerovalent copper (Cu*). The cold-temperature reduction of CuCNwLiX 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 OC with little homocoupling. Allyl, methallyl, and crotyl acetates also ...

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