Abstract
Mesityllithium has proven to be an effective iodine-lithium exchange reagent. Thus, carbolithiation reactions on 2-alkenyl-substituted N-(o-iodobenzyl)pyrroles have been accomplished avoiding side reactions to afford pyrroloisoquinolines in high yields (80-92%), improving the results obtained with t-BuLi. The carbolithiation reaction requires the use of electron-deficient alkenes. Mesityllithium has also been studied as an alternative to t-BuLi in Parham cyclization with other internal electrophiles (aldehyde, ketone, ester, amide), proving to be more selective and efficient than t-BuLi.
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