Novel phosphite palladium complexes and their application in C–P cross-coupling reactions

Li, Jie; Lutz, Martin; Spek, Anthony L.; Klink, Gerard P. M. van; Koten, Gerard van; Gebbink, Robertus J. M. Klein

doi:10.1016/j.jorganchem.2010.08.026

Cited by 28 publications

(4 citation statements)

References 94 publications

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“…Structures of single crystals of complex 5 were determined in trigonal space group R3̅ . Surprisingly, we found that two ligands coordinate in a trans fashion to a planar Pd dimer having two bridging and two terminal chloride ligands (Figure 3a), which was also found for other phosphole, 56 phosphite, 57 and regular phosphine ligands. The As−Pd 2 Cl 4 −As fragment forms an almost perfect plane with maximal deviations from the least-squares planes of only 0.082(5) Å for Cl1.…”

Section: ■ Results and Discussionsupporting

confidence: 72%

Rich Coordination Chemistry of π-Acceptor Dibenzoarsole Ligands

2017

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A series of dibenzoarsole (also known as 9-arsafluorene) derivatives have been prepared, and their coordination chemistry has been investigated. The different ligand topology and the arsenic substituents govern the reactivity of the ligands. We report various crystal structures of palladium and platinum complexes derived from this family of ligands. The biphenyl backbone of the bridged bidentate ligands allows very flexible coordination. We have also studied the application of an allylic Pd complex in nucleophilic substitution reactions, revealing that the benzoarsole substituent is susceptible to metal insertion.

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Section: ■ Results and Discussionsupporting

confidence: 72%

Rich Coordination Chemistry of π-Acceptor Dibenzoarsole Ligands

2017

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“…In two cases, hexagon-like moieties are not linked to the chains and stay as separated units (Figure S30, S32). [13] LICKAM CBr 4 0.86-0.87 [PtCl 2 (NCNEt 2 ) 2 ] [13] LICKIU CBr 4 0.92-0.98 [PdCl 2 (NCNMe 2 ) 2 ] [13] LIHMATC HBr 3 0.91 [PdCl 2 (NCNMe 2 ) 2 ] [13] LIHMEXC HI 3 0.89-0.90 [PtCl 2 (NCNMe 2 ) 2 ] [13] LIHMIBCHBr 3 0.92 [PtCl 2 (NCNCH(CH 2 ) 3 CH) 2 ] [20] UKAWOU CHI 3 0.87-0.89 [PtCl 2 (NCNMe 2 ) 2 ] [20] UKEKIG CHI 3 0.89-0.91 [PtBr 2 (NCNMe 2 ) 2 ] [20] UKELAZ CHI 3 0.89-0.90 [PtCl 2 (NCNEt 2 ) 2 ] [20] UKELEDC HI 3 0.87-0.94 [PPh 4 ][ReBr 4 (NO) 2 ] [21] BOJFOV CCl 4 0.95-0.99 [PdCl 2 (P(OC 12 H 8 O)OPh)] 2 [22] EJOHAN CHCl 3 0.97-0.99 [AsPh 4 ][W 2 Cl 2 (N 3 S 2 ) 3 ] [23] FEPVURCCl 4 0.98 [PtCl 2 (NHC(Et)(C 3 N 2 H 3 )] [24] MEHZAB CHCl 3 0.89-0.96 [SiBr 2 (OC(Ph)NHNC(Me) 2 ] [25] UFOYETCHCl 3 0.97-0.99 [NPr 4 ][CuBr 2 ] [26] HIGRAR CBr 4 0.85-0.91…”

Section: Resultsmentioning

confidence: 99%

Dihalomethanes as Bent Bifunctional XB/XB‐Donating Building Blocks for Construction of Metal‐involving Halogen Bonded Hexagons

Kashina

Kinzhalov

Smirnov

et al. 2019

Chemistry An Asian Journal

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The dihalomethanes CH 2 X 2 (X = Cl, Br,I )w ere cocrystallizedw ith the isocyanide complexes trans-[MX M 2 (CNC 6 H 4 -4-X C ) 2 ]( M= Pd, Pt;X M = Br,I ;X C = F, Cl, Br) to give an extended series comprising 15 X-ray structures of isostructural adducts featuring 1D metal-involving hexagonlike arrays. In these structures, CH 2 X 2 behavea sb ent bifunctional XB/XB-donating building blocks, whereas trans-ct as al inear XB/XB acceptors. Results of DFT calculations indicate that all XCH 2 -X···X M -M contacts are typical noncovalent interactions with estimated strengthsi nt he range of 1.3-3.2 kcal mol À1 .ACCDC search reveals that hexagon-likea rrays are rather commonb ut previously overlooked structural motives for adducts of transbis(halide) complexesand halomethanes.Figure 7. Aview of LIHMEXc rystal structure with hexagon-like fragment;additionally Pt···I interactions are shown.Figure 8. The Scheme of CSD search of structures with Y'···X-CH 2 -X···Y contacts( a), and structures with hexagonal-like fragments (b).

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“…To gain better understanding of the mechanism of the reaction, several attempts were undertaken to define the nature of the true active species. With this aim, a variety of poisons [Hg 0 , CS 2 , tetramethylthiourea (TMTU), and tetrabutylammonium bromide (TBAB)] was used . The Hg 0 test is most commonly used to confirm the role of Pd NPs in the catalytic reaction.…”

Section: Resultsmentioning

confidence: 85%