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Paper | Special issue | Vol 76, No. 1, 2008, pp.471-483
Published online, 17th April, 2008
DOI: 10.3987/COM-08-S(N)32
Silver-Catalyzed Synthesis of 1,2-Dihydroisoquinolines through Direct Addition of Carbon Pronucleophiles to ortho-Alkynylaryl Aldimines

Naoki Asao,* Salprima Yudha S., Tsutomu Nogami, and Yoshinori Yamamoto

*Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan

Abstract

AgOTf-catalyzed reaction of ortho-alkynyl-arylaldimines with various kinds of pronucleophiles afforded a variety of 1,2-dihydroisoquinoline derivatives in good to high yields. Treatment of ortho-alkynyl-arylaldimines with a stoichiometric amount of AgOTf, followed by the protonation with TfOH produced isoquinolinium trifluoromethanesulfonate, which suggested the formation of isoquinolinium intermediate in the present direct addition reaction.