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Communication | Special issue | Vol 90, No. 2, 2015, pp.847-856
Published online, 15th August, 2014
DOI: 10.3987/COM-14-S(K)72
■ Facile Preparation of 1,2-Dihydroisoquinolines from N-Benzylsulfonamides and Bromoacetylenes

Masahito Yamagishi, Azusa Ishii, Takeshi Hata, and Hirokazu Urabe*

*Department of Biomolecular Engineering, Graduate School of Bioscience and Biotechnology, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama 226-8501, Japan

Abstract

Nucleophilic addition of N-benzylsulfonamides to 1-bromo-1-alkynes proceeded in a highly regio- and stereoselective manner to give (Z)-N-benzyl-N-(1-bromo-1-alken-2-yl)sulfonamides. These adducts cyclized via Pd-catalyzed aromatic C-H bond activation to afford 1,2-dihydroisoquinolines in good yields.