Coordination chemistry of gold with N-phosphine oxide-substituted imidazolylidenes (POxIms)

被引:13
作者
Branzi, Lorenzo [1 ]
Baron, Marco [1 ]
Armelao, Lidia [1 ,2 ]
Rancan, Marzio [2 ]
Sgarbossa, Paolo [3 ]
Graiff, Claudia [4 ]
Poethig, Alexander [5 ,6 ]
Biffis, Andrea [1 ]
机构
[1] Univ Padua, Dipartimento Sci Chim, Via F Marzolo 1, I-35131 Padua, Italy
[2] Univ Padua, CNR, ICMATE, Dipartimento Sci Chim, Via F Marzolo 1, I-35131 Padua, Italy
[3] Univ Padua, Dipartimento Ingn Ind, Via F Marzolo 9, I-35131 Padua, Italy
[4] Univ Parma, Dipartimento Sci Chim Vita & Sostenibilita Ambien, Parco Area Sci 17-A, I-43124 Parma, Italy
[5] Tech Univ Munich, Catalysis Res Ctr, Ernst Otto Fischer Str 1, D-85747 Garching, Germany
[6] Tech Univ Munich, Dept Chem, Ernst Otto Fischer Str 1, D-85747 Garching, Germany
关键词
HETEROCYCLIC CARBENE; COMPLEXES; LIGANDS; AU; HYDROAMINATION; TRICATION; EFFICIENT; INSIGHTS; ANIONS; NHC;
D O I
10.1039/c9nj04911h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
N-Phosphine oxide-substituted imidazolylidenes (POxIms) have been employed as heteroditopic ligands towards gold centres. Both bis-carbene and mono-carbene gold(i) complexes have been obtained, depending on the steric bulk of the employed POxIm ligand. Oxidation of the gold(i) complexes with halogens or halogen synthons allows access to both bis-carbene and mono-carbene gold(iii) complexes, depending on the nature of the starting gold(i) complex and on the oxidation conditions. In all these complexes, the phosphanyl oxide moiety of the ligand is found to not be coordinated by the gold centre, although the crystallographic and spectroscopic characterization of the compounds suggests in most cases the existence of weak electrostatic interactions. A preliminary screening of the complexes as precatalysts in the intermolecular hydroamination of phenylacetylene with mesitylamine has also been carried out.
引用
收藏
页码:17275 / 17283
页数:9
相关论文
共 40 条
[1]   Gold as a catalyst. Part I. Nucleophilic addition to the triple bonds [J].
Alyabyev, Sergey B. ;
Beletskaya, Irina P. .
RUSSIAN CHEMICAL REVIEWS, 2017, 86 (08) :689-749
[2]   Single-Step Synthesis of Dinuclear Neutral Gold(I) Complexes with Bridging Di(N-heterocyclic carbene) Ligands and Their Catalytic Performance in Cross Coupling Reactions and Alkyne Hydroamination [J].
Baron, Marco ;
Battistel, Edoardo ;
Tubaro, Cristina ;
Biffis, Andrea ;
Armelao, Lidia ;
Rancan, Marzio ;
Graiff, Claudia .
ORGANOMETALLICS, 2018, 37 (22) :4213-4223
[3]   A square planar gold(III) bis-(1,1′-dimethyl-3,3′-methylene-diimidazol-2,2′-diylidene) trication as an efficient and selective receptor towards halogen anions: the cooperative effect of Au ••• X and X ••• HC interactions [J].
Baron, Marco ;
Dall'Anese, Anna ;
Tubaro, Cristina ;
Orian, Laura ;
Di Marco, Valerio ;
Bogialli, Sara ;
Graiff, Claudia ;
Basato, Marino .
DALTON TRANSACTIONS, 2018, 47 (03) :935-945
[4]   Gold(III) Bis(di-N-heterocyclic carbene) Square Planar Trication with Axial Ligand Interactions with Bromides from Ag/Br Counteranion Assemblies [J].
Baron, Marco ;
Tubaro, Cristina ;
Cairoli, Maddalena L. C. ;
Orian, Laura ;
Bogialli, Sara ;
Basato, Marino ;
Natile, Marta M. ;
Graiff, Claudia .
ORGANOMETALLICS, 2017, 36 (12) :2285-2292
[5]   Insights into the Halogen Oxidative Addition Reaction to Dinuclear Gold(I) Di(NHC) Complexes [J].
Baron, Marco ;
Tubaro, Cristina ;
Basato, Marino ;
Isse, Abdirisak Ahmed ;
Gennaro, Armando ;
Cavallo, Luigi ;
Graiff, Claudia ;
Dolmella, Alessandro ;
Falivene, Laura ;
Caporaso, Lucia .
CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (29) :10211-10224
[6]   Advances in Transition-Metal-Catalysed Alkyne Hydroarylations [J].
Biffis, Andrea ;
Tubaro, Cristina ;
Baron, Marco .
CHEMICAL RECORD, 2016, 16 (04) :1742-1760
[7]   Palladium(II) Complexes with N-Phosphine Oxide-Substituted Imidazolylidenes (Poxlms): Coordination Chemistry and Catalysis [J].
Branzi, Lorenzo ;
Franco, Dario ;
Baron, Marco ;
Armelao, Lidia ;
Rancan, Marzio ;
Sgarbossa, Paolo ;
Biffis, Andrea .
ORGANOMETALLICS, 2019, 38 (10) :2298-2306
[8]  
Bruker, 2015, APEX3 SAINT
[9]   Straightforward synthesis of [Au(NHC)X] (NHC = N-heterocyclic carbene, X = Cl, Br, I) complexes [J].
Collado, Alba ;
Gomez-Suarez, Adrian ;
Martin, Anthony R. ;
Slawin, Alexandra M. Z. ;
Nolan, Steven P. .
CHEMICAL COMMUNICATIONS, 2013, 49 (49) :5541-5543
[10]   Synthesis, characterization and reactivity of N-heterocyclic carbene gold(III) complexes [J].
de Fremont, Pierre ;
Singh, Rohit ;
Stevens, Edwin D. ;
Petersen, Jeffrey L. ;
Nolan, Steven P. .
ORGANOMETALLICS, 2007, 26 (06) :1376-1385