CLEAN AND CONVENIENT PROCEDURE FOR CONVERTING PRIMARY ALKYL IODIDES AND ALPHA,OMEGA-DIIODOALKANES INTO THE CORRESPONDING ALKYLLITHIUM DERIVATIVES BY TREATMENT WITH TERT-BUTYLLITHIUM

Whereas lithium—halogen exchange2 has been widely used for generating alkenyl- and aryllithiums,3 its application to the preparation of alkyllithiums has not been widely reported. We have recently noted that the reaction of alkyl iodides with 2 equiv of t-BuLi can provide a clean, high-yielding, and convenient method for preparing the corresponding alkyllithiums as discrete products.4 This method has also been used to generate alkene- and alk-yne-containing alkyllithiums for both mechanistic5 and synthetic6 purposes. These results suggested to us that the method might provide a general route to primary alkyllithiums, which in some cases is superior to the previously developed alternatives7. © 1990, American Chemical Society. All rights reserved.