Abstract
Lithiation of various substrates, such as chlorinated acetals, α-chloro ether, dichloro derivatives benzo-fused heterocycles, and allyl and benzyl derivatives, with excess lithium powder in the presence of a catalytic amount of soluble linear or insoluble cross-linked arene (naphthalene or biphenyl)-based polymers yields the expected organolithium intermediates. The latter react with electrophiles either in two steps or under Barbier-type reaction conditions to afford the corresponding adducts. The catalyst is easily recuperated by filtration at the end of the process, and the procedure can be regarded as a reasonable alternative to the use of free arenes as electron carrier in lithiation reactions.
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Candela, P., Gómez, C. & Yus, M. Lithiation Reactions Catalyzed by Linear and Cross-Linked Arene-Based Polymers. Generation of Functionalized Organolithium Compounds. Russian Journal of Organic Chemistry 40, 795–801 (2004). https://doi.org/10.1023/B:RUJO.0000044541.84132.e5
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DOI: https://doi.org/10.1023/B:RUJO.0000044541.84132.e5