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8315319 
Journal Article 
Rhodium/phosphine/amine-HBr catalyst system for highly selective cross-cyclodimerization of aryl- and alkylalkynes: Efficient access to multisubstituted naphthalene derivatives 
Sakabe, K; Tsurugi, H; Hirano, K; Satoh, T; Miura, M 
2010 
Yes 
Chemistry: A European Journal
ISSN: 0947-6539
EISSN: 1521-3765 
16 
2 
445-449 
English 
19938020 
WOS:000274265100009 
The rhodium/phosphine/amine.HBr catalyst system directed toward the highly chemoselective synthesis of multisubstituted naphthalene derivatives from two different internal alkynes was investigated. Under N2 atmosphere, [(RhC1(cod)}2], PPh3, Py.HBr, 1a, 2a, o-xylene and 1- methylnaphthalene were placed in a 20 mL two-necked reaction flask equipped with a reflux condenser. After the mixture was heated at 160°C for 6 h, the consumption of 1a was checked by GC analysis. The resulting mixture was allowed to cool to room temperature and then concentrated under reduced pressure. The residue obtained was purified by column chromatography on silica gel with hexane as an eluent to give 3-phenyl-1,2-dipropylnaphthalene in 84% yield. The catalyst enabled the use of alkenes as the coupling components, providing the dihydronaphthalenes. 
Alkynes; Cross-cyclodimerization dihydronaphthalenes; Naphthalenes; Rhodium