Synthesis of naphtho[1,8-bc]pyran derivatives and related compounds through hydroxy group directed C-H bond cleavage under rhodium catalysis.

Satoshi Mochida, Masaki Shimizu, Koji Hirano, Tetsuya Satoh, Masahiro Miura

Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan.

Chemistry, an Asian journal 2010 Apr 1

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The straightforward and efficient synthesis of naphtho[1,8-bc]pyran derivatives and related polycyclic compounds is achieved by the rhodium-catalyzed oxidative coupling of 1-naphthols or other phenolic and alcoholic substrates with alkynes. In these annulation reactions, the hydroxy groups effectively act as the key function for the regioselective C-H bond cleavage.

Citation

Satoshi Mochida, Masaki Shimizu, Koji Hirano, Tetsuya Satoh, Masahiro Miura. Synthesis of naphtho[1,8-bc]pyran derivatives and related compounds through hydroxy group directed C-H bond cleavage under rhodium catalysis. Chemistry, an Asian journal. 2010 Apr 1;5(4):847-51