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Base-Induced Dehydrogenative and Dearomative Transformation of 1-Naphthylmethylamines to 1,4-Dihydronaphthalene-1-carbonitriles.

Yoshiya SekiguchiJia Hao PangJia Sheng NgJiahua ChenKohei WatanabeRyo TakitaShunsuke Chiba
Published in: JACS Au (2022)
Solvothermal treatment of 1-naphthylmethylamine with potassium hydride (KH) or n -butyllithium ( n -BuLi)-potassium t -butoxide ( t -BuOK) in THF induces unusual two consecutive β-hydride eliminations to form 1-naphthonitrile and KH. The freshly generated KH is hydridic enough to undergo dearomative hydride addition to the resultant 1-naphthonitrile regioselectively at the C4 position to afford α-cyano benzylic carbanion, which could be functionalized by a series of electrophiles, liberating the corresponding 1,4-dihydronaphthalene-1-carbonitriles having a quaternary carbon center.
Keyphrases
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