Journal
JOURNAL OF ORGANOMETALLIC CHEMISTRY
Volume 690, Issue 12, Pages 2956-2966Publisher
ELSEVIER SCIENCE SA
DOI: 10.1016/j.jorganchem.2005.03.021
Keywords
antimony; cross-coupling; intermolecular coordination; ethynylstibane; vinyl halide; aryl halide
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The reaction of ethynylstibanes (la-g) with vinyl halides or triflate in the presence of a palladium catalyst led to the formation of cross-coupling products (5a-g, 10-12) in good to moderate yield, along with homo-coupling products (6a-g). A similar reaction of ethynyldiphenyistibane (1a) with aryl iodides (13a-i) also gave cross-coupling products (14a-i), although the yields were relatively low. The yields of the cross-coupling products were highly dependent on the nature of the solvent employed, and good results were obtained when the reaction was carried out in HMPA or amines such as diethylamine and morpholine. The results imply that HMPA and amine used as solvents facilitate transmetallation of the ethynyl group on I to the palladium by intermolecular coordination between antimony and oxygen (for HMPA) or nitrogen (for amine). (c) 2005 Elsevier B.V. All rights reserved.
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