Carbon–carbon bond formations at the benzylic positions of N-benzylxanthone imines and N-benzyldi-1-naphthyl ketone imine

• Published in: Tetrahedron Vol. 65; no. 26; pp. 5125 - 5131
• Main Authors: Niwa, Takashi, Suehiro, Takafumi, Yorimitsu, Hideki, Oshima, Koichiro
• Format: Journal Article Conference Proceeding
• Language: English
• Published: OXFORD Elsevier Ltd 27.06.2009; Elsevier
• Subjects: Benzylic alkylation; Benzylic arylation; Chemistry; Chemistry, Organic; Condensed benzenic and aromatic compounds; Deprotonation; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives; N-Benzyl imines; Organic chemistry; Palladium; Physical Sciences; Preparations and properties; Science & Technology; N-Benzyl imines; Benzylic arylation; Benzylic alkylation; Palladium; Deprotonation; HALIDES; ALPHA-ARYLATION; C-H ACTIVATION; CYCLOPENTADIENES; ARYL BROMIDES; PYRROLIDINES; HETEROCYCLES; PALLADIUM-CATALYZED SYNTHESIS; DERIVATIVES; SP; Arylation; Palladium complex; Transition metal; Imine; Oxygen heterocycle; Ketone; Naphthalene derivatives; Alkylation; Organic halogen compounds; Amine; Xanthene derivatives; Benzylic compound; Addition reaction; Cesium Hydroxides; Aromatic compound; Catalysis; Platinoid
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2009.02.034

Two N-benzyl imines are designed to allow for carbon–carbon bond formations at the aminated benzylic positions. Direct benzylic arylation reactions of N-benzylxanthone imine with aryl chlorides proceed under palladium catalysis in the presence of cesium hydroxide, yielding the corresponding benzhydrylamine derivatives. Alkylation reactions of N-benzyldi-1-naphthyl ketone imine with alkyl halides in the presence of potassium tert-butoxide afford the corresponding 1-phenylalkylamines in high yields. Conjugate addition of N-benzyldi-1-naphthyl ketone imine is also described. [Display omitted]