Structurally engineered deprotonation/alumination of THF and THTP with retention of their cycloanionic structures

Crosbie, Elaine and Garcia-Alvarez, Pablo and Kennedy, Alan R. and Klett, Jan and Mulvey, Robert E. and Robertson, Stuart D. (2010) Structurally engineered deprotonation/alumination of THF and THTP with retention of their cycloanionic structures. Angewandte Chemie, 49 (49). pp. 9388-9391. ISSN 0044-8249

Abstract

Metalation has served well for over 80 years as a vehicle for transforming inert CH bonds in organic compounds to reactive Cmetal bonds.[1] Progress in metalation was accelerated greatly by the development of DoM (directed orthometalation), [2] pioneered by Snieckus, Beak, and others, a special type of lithiation (aromatic CH to Cd Li d+) reliant on the high polarity of carbon–lithium bonds in organolithium reagents. Many other metals could not engage in metalation due to the lower polarity/lower reactivity of their corresponding carbon–metal bonds. However, this obstacle has now been cleared by the recognition that when part of a mixed-metal system or other multicomponent mixture, these metals (for example, magnesium, zinc, aluminum or manganese) can exhibit greatly enhanced metalating properties often superior in terms of functional-group compatibility or reaction conditions to that of lithium. Interest in these new “low polarity” metalating agents is widespread with coverage in fundamental chemistry journals,[3] process chemistry journals, [4] interdisciplinary science journals, [5] and in news items in scientific media.

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