Science of Synthesis

Subramanian, L. R., Science of Synthesis, (2004) 19, 190.

Electrophilic cyanating agents have been used to cyanate organometallic compounds (see Section ‌19.5.4.1‌), but electrophilic cyanation of 2-bromonaphthalene and 9-bromoanthracene (‌64‌) with 1H-1,2,3-benzotriazole-1-carbonitrile (‌65‌)[‌72‌] has been reported.[‌73‌] First, conversion of the aryl bromide into an organometallic is necessary; this is achieved by treatment with butyllithium. Inverse addition of the lithium salt to 1H-1,2,3-benzotriazole-1-carbonitrile (‌65‌) affords the nitrile in good yield, e.g. anthracene-9-carbonitrile (‌66‌) (‌Scheme 27‌).[‌73‌]

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