Regioselective Metalations of Pyrimidines and Pyrazines by Using Frustrated Lewis Pairs of BF₃⋅OEt₂ and Hindered Magnesium– and Zinc–Amide Bases

Abstract

Born of frustration: Using the frustrated Lewis pairs TMP–metal and BF3⋅OEt2 allows the regioselective metalation of pharmaceutically relevant diazines, such as pyrimidines, purines, and pyrazines. These metalations are often complementary to prior deprotonations performed without BF3⋅OEt2. Especially attractive is a new sequential regioselective full functionalization of the pyrazine scaffold with a bulky (TMS)2CH substituent. As a service to our authors and readers, this journal provides supporting information supplied by the authors. Such materials are peer reviewed and may be re-organized for online delivery, but are not copy-edited or typeset. Technical support issues arising from supporting information (other than missing files) should be addressed to the authors. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.