Journal
TETRAHEDRON LETTERS
Volume 45, Issue 14, Pages 2923-2926Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2004.02.062
Keywords
thiosemicarbazone; O, N, S-ligand; phosphine-free ligand; palladium complex; Heck reaction; homogeneous catalysis
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A novel palladium complex with salicylaldehyde N(4)-ethylthiosemicarbazone has been synthesized and according to its crystal structure the ligand is bound to the metal in an 0, N, S-terdentate coordination mode. This phosphorus-free system efficiently catalyzes the Heck reaction of aryl bromides (from electron-rich to electron-poor) with styrene under argon, with turnover numbers of up to 43,000, at 150 degreesC after 24h, and with a selectivity toward trans-stilbenes ranging from 92 to 96%. In air, for activated aryl bromides and for a palladium concentration of 1 mM, the yields are essentially the same as those obtained when the reaction was performed under argon. (C) 2004 Elsevier Ltd. All rights reserved.
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