Abstract
The novel Pd(0)-azobenzene complex (ITMe)2Pd(PhN═NPh) (5) (ITMe = 1,3,4,5-tetramethylimidazol-2-ylidene) has been isolated and characterized in the solid state and by cyclic voltammetry. Its reactivity toward E–E′ bonds (E, E′ = Si, B, Ge) has been compared with that of the known carbene complex (ITMe)2Pd(PhC≡CPh) (2). Whereas 2 reacts with all E–E′ bonds studied, 5 only reacted with B–B and B–Si moieties, echoing our previous catalytic studies on azobenzenes.
Highlights
These encouraging findings have led us to further explore the scope and reactivity of 2
We wished to explore the synthesis of NHC-containing azobenzene complexes related to 2 to shed some light on the aforementioned catalytic additions of E−E′ bonds to azobenzenes
Given our success in achieving low catalyst loadings and mild conditions in a number of E−E′ additions to alkynes, we wished to investigate the use of complexes such as 2 in the activation of Ge−Ge bonds
Summary
These complexes display tremendous versatility in high turnover number (TON) catalytic reactions.− Recent reports from our groups have focused on the much smaller carbene ITMe (ITMe = 1,3,4,5tetramethylimidazol-2-ylidene), and its low percentage buried volume Pd(0) complex Pd(ITMe)2 [1], as well as the isolable alkyne-bearing complex (ITMe)2Pd(PhC CPh) [2].5−7 Both can cleave nonactivated E−E′ bonds (E, E′= Si, B), resulting in Pd(II) complexes that can undergo an atomeconomical, Z-selective addition to internal alkynes affording disilylated or silaborated alkenes. Given our success in achieving low catalyst loadings and mild conditions in a number of E−E′ additions to alkynes, we wished to investigate the use of complexes such as 2 in the activation of Ge−Ge bonds.
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