Base-induced dehydrogenative and dearomative transformation of 1-naphthylmethylamines to 1,4-dihydronaphthalene-1-carbonitriles

• Main Authors: Sekiguchi, Yoshiya, Pang, Jia Hao, Ng, Jia Sheng, Chen, Jiahua, Watanabe, Kohei, Takita, Ryo, Chiba, Shunsuke
• Other Authors: School of Chemistry, Chemical Engineering and Biotechnology
• Format: Article
• Language: English
• Published: 2023
• Subjects: Engineering::Chemical engineering; Dearomatization; Beta-Hydride Elimination
• Online Access: https://hdl.handle.net/10356/164489
• Institution: Nanyang Technological University

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 hydri...