Dinuclear and mononuclear palladium complexes having N,N'-bis[2-(diphenylphosphino)phenyl]amidinate (DPFAM) as a ligand catalyzed the cross-addition of triisopropylsilylacetylene (TIPSA) to unactivated internal alkynes, giving enynes selectively. When palladium catalysts having PPh3, TDMPP, dppe, or dppf were used, dimers of TIPSA were obtained as major products. The reactions of TIPSA with several terminal alkynes also gave cross-adducts selectively, although the yields were moderate.
Selective cross-addition of triisopropylsilylacetylene (TIPSA) to unactivated alkynes is catalyzed by dinuclear and mononuclear palladium complexes supported by a multidentate ligand, N,N'-bis[2-(diphenylphosphino)phenyl]formamidine (dpfamH). While the addition reactions of TIPSA to dialkylacetylenes using palladium catalysts supported by monodentate and bidentate ligands gives dimers of TIPSA as major products, the reactions with the palladium complexes supported by dpfam affords cross-adducts selectively, in which the yields of TIPSA dimers are less than 5 %. The addition of TIPSA to monoalkylacetylenes also gives cross-adducts as major products, although the selectivity and yield are moderate.
Organo-silicon compounds S 0060 Palladium-Catalyzed Selective Cross-Addition of Triisopropylsilylacetylene to Internal and Terminal Unactivated Alkynes. -The reaction proceeds generally with high regio-and (E)-selectivity. The presence of a silyl group in the products allows their further functionalization. -(TSUKADA*, N.; NINOMIYA, S.; AOYAMA, Y.; INOUE, Y.; Org. Lett. 9 (2007) 15, 2919-2921; Grad. Sch. Eng., Tohoku Univ., Sendai 980, Japan; Eng.) -R. Steudel 47-173
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