2015
DOI: 10.1002/anie.201505464
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A Stimuli‐Responsive Rotaxane–Gold Catalyst: Regulation of Activity and Diastereoselectivity

Abstract: A rotaxane-based Au catalyst was developed and the effect of the mechanical bond on its behavior was studied. Unlike the non-interlocked thread, the rotaxane requires a catalytically innocent cofactor, the identity of which significantly influences both the yield and diastereoselectivity of the reaction. Under optimized conditions, AuI (the catalyst), AgI (to abstract the Cl− ligand), and CuI (the cofactor) combine to produce a catalyst with excellent activity and selectivity.

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Cited by 147 publications
(68 citation statements)
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“…Embedded in a protein, the switching of the photoactive molecular unit between two well‐defined structural states causes, through specific interactions with the protein environment, a long‐range effect that is the basis for the biological activity . Such a level of control of molecular motion on the nanoscale is crucial not only for biological systems but also for the development of new efficient functional materials for a wide range of applications (for example, catalysis, drug delivery, and molecular computers) . The functional performance of these materials depends not only on the intrinsic switching properties of the employed molecular units but also, as illustrated by the molecular‐level description of human sight, on how switching is transmitted to the macroscopic world.…”
Section: Figurementioning
confidence: 99%
“…Embedded in a protein, the switching of the photoactive molecular unit between two well‐defined structural states causes, through specific interactions with the protein environment, a long‐range effect that is the basis for the biological activity . Such a level of control of molecular motion on the nanoscale is crucial not only for biological systems but also for the development of new efficient functional materials for a wide range of applications (for example, catalysis, drug delivery, and molecular computers) . The functional performance of these materials depends not only on the intrinsic switching properties of the employed molecular units but also, as illustrated by the molecular‐level description of human sight, on how switching is transmitted to the macroscopic world.…”
Section: Figurementioning
confidence: 99%
“…Mechanically interlocked molecules (MIM) such as rotaxanes and catenanes have progressed from compounds of aesthetic interesta nd curiosity to an active area of contemporary chemical research, with applications in nanotechnology, [1][2][3][4][5][6][7][8] drug delivery, [9][10][11][12] catalysis, [13][14][15] materials science [16][17][18][19][20][21] and molecular recognition. [22][23][24][25] Amongst the supramolecular interactions, which imbue interlocked host systemswith their unique recognition properties for anion guest species, halogen bonding (XB), the highly directional attractive non-covalent interaction between an electron-deficient halogen atom and aL ewis base, [26,27] remains the least exploited.…”
Section: Introductionmentioning
confidence: 99%
“…[5][6][7][8] . [9][10][11] Thiosemicarbazonebased ligands have been used to generate interesting complexes with a range of potential applications, however one area that appeals to us is their use in Fe(III) spincrossover (SCO) systems. [12][13][14][15][16][17] Most examples of thiosemicarbazone-based SCO active complexes use simple thiosemicarbazides and salicylaldehyde (SA) derivatives (e.g.…”
Section: Introductionmentioning
confidence: 99%