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8.1.14.2.2 Variation 2: Amide Directed ortho-Lithiation Groups

DOI: 10.1055/sos-SD-008-00213

Gribble, G. W.Science of Synthesis, (20068364.

The seminal work by Beak,[‌19‌,‌57‌,‌69‌‌72‌] Snieckus,[‌8‌,‌11‌,‌13‌,‌19‌,‌73‌] and Gschwend[‌16‌,‌74‌,‌75‌] demonstrates the importance of the amide directing group in aromatic lithiation. Examples 19, 21, and 22 in Scheme 9 are representative. Further reaction of aryllithium compound 19 with an electrophile, e.g. benzaldehyde, gives substituted benzamides such as 20.[‌73‌]

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