Synthesis of Fluorene Derivatives through Rhodium-Catalyzed Dehydrogenative Cyclization

• Published in: Angewandte Chemie (International ed.) Vol. 51; no. 22; pp. 5359 - 5362
• Main Authors: Morimoto, Keisuke, Itoh, Masaki, Hirano, Koji, Satoh, Tetsuya, Shibata, Yu, Tanaka, Ken, Miura, Masahiro
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 29.05.2012; WILEY‐VCH Verlag; Wiley; Wiley Subscription Services, Inc
• Edition: International ed. in English
• Subjects: Activation; Bonding; Chemistry; Chemistry, Multidisciplinary; Cleavage; cyclizations; CC coupling; CH activation; Decarboxylation; Dehydrogenation; Derivatives; homogeneous catalysis; Physical Sciences; Rhodium; Science & Technology; Synthesis; ACTIVATION; DIRECT ARYLATION; CARBON; C?H activation; INTERNAL ALKYNES; H BOND FUNCTIONALIZATION; CLEAVAGE; C?C coupling; cyclizations; OLEFINATION; homogeneous catalysis; COUPLING REACTIONS; rhodium; C-H; BENZOIC-ACIDS
• ISSN: 1433-7851; 1521-3773
• DOI: 10.1002/anie.201201526

Doubling up: Two CH bond activations took place efficiently upon treatment of 1 with a rhodium catalyst to form dehydrogenative cyclization products 2. Furthermore, 3 undergoes similar cyclization and subsequent decarboxylation through the cleavage of two CH bonds and one CC bond. Both reactions provide straightforward routes to the fluorene framework.