Coordination Behavior of Sterically Protected Phosphaalkenes on the AuCl Moiety Leading to Catalytic 1,6‐Enyne Cycloisomerization

Freytag, Mat­thias; Ito, Shigekazu; Yoshifuji, Masaaki

doi:10.1002/asia.200600155

Cited by 69 publications

(49 citation statements)

References 66 publications

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“…93 The complexes could be recovered and reused. The authors speculate that the low-lying LUMO of the phosphorus-carbon double bond may increase the electrophilicity of the formally neutral Au center, presumably via increased backbonding from Au into the ligand.…”

Section: Cascade Reactions Initiated By Carbon Nucleophiles With πmentioning

confidence: 99%

Ligand Effects in Homogeneous Au Catalysis

2008

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F. Dean Toste received his B.Sc. and M.Sc. degrees in chemistry from the University of Toronto where he worked with Prof. Ian W. J. Still. In 1995, he began his doctoral studies at Stanford University under the direction of Professor Barry M. Trost. Following postdoctoral studies with Professor Robert H. Grubbs at Caltech, he joined the faculty at the University of California, Berkeley, in 2002, and was promoted to Associate Professor in 2006. Current research in his group is aimed towards the design of catalysts and catalytic reactions and the application of these methods to chemical synthesis.

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Section: Cascade Reactions Initiated By Carbon Nucleophiles With πmentioning

confidence: 99%

Ligand Effects in Homogeneous Au Catalysis

2008

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“…(130)]. [151] The selective formation of cyclohexadiene was therefore a specificity of silyloxy-substituted alkynes. [156] The cyclization of enyne 399 afforded the cyclopropyl derivative 400 by using a standard protocol used with platinum catalysts [Eq.…”

Section: Enyne Rearrangementsmentioning

confidence: 99%

Cycloisomerization of 1,n‐Enynes: Challenging Metal‐Catalyzed Rearrangements and Mechanistic Insights

Michelet¹,

Toullec²,

Genêt³

2008

Angew Chem Int Ed

937

248

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Metal-catalyzed cycloisomerization reactions of 1,n-enynes have appeared as conceptually and chemically highly attractive processes as they contribute to the highly demanded search for atom economy and allow the discovery of new reactions. Since the pioneering studies with palladium by the research group of Barry Trost in the mid-1980s, several other metals have been identified as excellent catalysts for the rearrangement of enyne skeletons. Moreover, the behavior of 1,n-enynes may be influenced by other functional groups such as alcohols, aldehydes, ethers, alkenes, or alkynes, thus enhancing the molecular complexity of the synthesized products. Apart from the intrinsic rearrangements of 1,n-enynes, several tandem reactions incorporating intramolecular trapping agents or intermolecular partners have been discovered. This Review aims to highlight the main contributions in this field of catalysis and to propose and comment on the mechanistic insights of the recent discoveries.

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“…Shorter intramolecular aurophilic interactions have been found in the quaterthiophene than in the bithiophene derivative. Chains are obtained for Z ¼ C:C (whose luminescent properties have been studied), trans-CH¼CH, and CH 2 C(¼CH 2 )CH 2 [197][198][199][200][201][202][203][204][205][206][207][208].…”

Section: Complexes With Bridging Bidentate Ligandsmentioning

confidence: 99%

Gold–Gold Interactions

Crespo

2008

Modern Supramolecular Gold Chemistry

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This chapter focuses mainly on closed shell gold(I) atoms which are found to feel attraction among themselves. This attraction is able to modify expected geometries or support one-, two-or three-dimensional arrays and also leads to interesting properties. Closed shell metal cations are expected to repel each other. Nevertheless, an important number of examples containing [d 8 -d 10 -s 2 ] interactions are known. Particularly strong evidence has been accumulated on the attraction between two or more d 10 shells. In the case of gold(I) such attraction between two or more monovalent gold(I) ions in compounds has been observed structurally for a long time. In these situations the gold centers approach each other to a distance of between 2.7 and 3.3 Å. This range includes the distance between gold atoms in gold metal and approaches, or even overlaps with the range of distances found in the few real Au-Au single bonds. Schmidbaur coined the name aurophilic attraction in 1990 and defined it as the unprecedented affinity between gold atoms even with closed-shell electronic configurations and equivalent electrical charges [1]. Since that moment, aurophilicity has become one of the hot topics in gold chemistry, at first with the aim of understanding such interaction, more recently because of the observation that it may play an important role in interesting properties, thus understanding and modulating aurophilic interactions could help to govern these properties, which include the optical behavior. Although different origins are possible for the luminescent emissions of coordination complexes, such as intraligand transitions (ILT), ligand to metal or metal to ligand charge transfer transitions (LMCT, MLCT) and metal centered (MCT) transitions, in many luminescent gold complexes the emissions have been related to the presence of aurophilic interactions.Information about aurophilicity and chemical situations in which it is observed may be found in different works that may be classified as those which analyse closed shell interactions in general [2], those focused on aurophilicity [1,3], and others which analyze the role of these interactions in coordination [4] and organometallic gold Modern Supramolecular Gold Chemistry: Gold-Metal Interactions and Applications. Edited by Antonio Laguna

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Coordination Behavior of Sterically Protected Phosphaalkenes on the AuCl Moiety Leading to Catalytic 1,6‐Enyne Cycloisomerization

Cited by 69 publications

References 66 publications

Ligand Effects in Homogeneous Au Catalysis

Ligand Effects in Homogeneous Au Catalysis

Cycloisomerization of 1,n‐Enynes: Challenging Metal‐Catalyzed Rearrangements and Mechanistic Insights

Gold–Gold Interactions

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