Nitriles lateral lithiation

Lateral lithiation of nitriles can be achieved—and self-condensation avoided—if LiTMP is used in THF at —78°C (Scheme 199/ . 

Gschwend reported the ortho lithiation of aniline pivalamides and subsequent addition to nitriles and carbonyls in 1979. A few years later, Wender used a similar aryllithium (11), obtained by metal-halogen exchange, in a new synthesis of indoles (Scheme 7). An analogous metalation occurs when N-phenylimidazol-2-ones are treated with LDA in THF at -78 C. ... 

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