Insertion reaction between planar chiral cyclopalladated derivatives of ferrocene and diphenylacetylene

Add time:09/24/2019    Source:sciencedirect.com

The reaction between diphenylacetylene and the planar chiral halogeno-bridged cyclopalladated compounds of ferrocene, [Pd{(η5-C5H3C(CH3)NNCH2CH2CH2CHCH2OCH3)Fe(η5-C5H5)}(μ-X)]2 [X=Cl: syn-(−)-(Sp,R,R,Sp)-1, syn-(−)-(Rp,R,R,Rp)-1, syn-(+)-(Rp,S,S,Rp)-1 and syn-(−)-(Sp,S,S,Sp)-1; X=Br: syn-(−)-(Sp,R,R,Sp)-2, syn-(−)-(Rp,R,R,Rp)-2, syn-(+)-(Rp,S,S,Rp)-2 and syn-(−)-(Sp,S,S,Sp)-2], afforded monomeric products in which one or two alkynes had been inserted into the PdC bond. Mono-insertion of alkyne occurred when reacting these compounds with stoichiometric amounts of diphenylacetylene, whereas bi-insertion was achieved with excess diphenylacetylene. The structures of mono-insertion compounds PdX(η5−C5H3(PhCCPh)C(CH3)NNCH2CH2CH2CHCH2OCH3)Feη5−C5H5 [X=Cl: (−)-(Sp,S)-3; X=Br: (−)-(Sp,S)-4] and bi-insertion compounds PdX(η5−C5H3{η3−(PhCCPhPhCCPh)}CCH3NNCH2CH2CH2CHCH2OCH3)Feη5−C5H5 [X=Cl: (−)-(Sp,R)-5, (+)-(Rp,S)-5; X=Br: (−)-(Sp,R)-6, (+)-(Rp,R)-6] have been determined by single-crystal X-ray analysis.

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