Permethylated NHC-capped a - and b -cyclodextrins (ICyDMe) Regioselective and enantioselective gold-catalysis in pure water.

A series of water-soluble encapsulated copper(I), silver(I) or gold(I) complexes based on NHC-capped permethylated cyclodextrins ( ICyD Me ) were developed and used as catalysts in pure water for hydration, lactonization, hydroarylation and cycloisomerization reactions. ICyD Me ligands gave cavity-based high regioselectivity in hydroarylations, and high enantioselectivities in gold-catalyzed cycloisomerizations reactions giving up to 98% ee in water. These ICyD Me are therefore useful ligands for selective catalysis in pure water.

[1]  E. Derat,et al.  β-Cyclodextrin–NHC–Gold(I) Complex (β-ICyD)AuCl: A Chiral Nanoreactor for Enantioselective and Substrate-Selective Alkoxycyclization Reactions , 2020, ACS Catalysis.

[2]  M. Delius,et al.  Supramolekulare Chemie von gespannten Kohlenstoffnanoreifen , 2020, Angewandte Chemie.

[3]  M. Delius,et al.  The Supramolecular Chemistry of Strained Carbon Nanohoops. , 2020, Angewandte Chemie.

[4]  Hülya Sak,et al.  Sustainable Gold Catalysis in Water Using Cyclodextrin‐tagged NHC‐Gold Complexes , 2019, ChemCatChem.

[5]  Christian Würtele,et al.  A bio-inspired imidazole-functionalised copper cage complex. , 2019, Chemical communications.

[6]  Joost N H Reek,et al.  Gold Catalysis in (Supra)Molecular Cages to Control Reactivity and Selectivity , 2018, ChemCatChem.

[7]  J. Djukic,et al.  Benzimidazolium- and Benzimidazolilydene-Capped Cyclodextrins: New Perspectives in Anion Encapsulation and Gold-Catalyzed Cycloisomerization of 1,6-Enynes. , 2018, Chemistry.

[8]  Bastien Chatelet,et al.  Covalent Cages with Inwardly Directed Reactive Centers as Confined Metal and Organocatalysts , 2018, European Journal of Organic Chemistry.

[9]  C. Su,et al.  "Calix[4]-box" cages promote the formation of amide bonds in water in the absence of coupling reagents. , 2018, Chemical communications.

[10]  H. Plenio,et al.  Bispentiptycenyl-N-Heterocyclic Carbene (NHC) Gold Complexes: Highly Active Catalysts for the Room Temperature Hydration of Alkynes , 2018, Advanced Synthesis & Catalysis.

[11]  S. Roland,et al.  Confinement of Metal-N-Heterocyclic Carbene Complexes to Control Reactivity in Catalytic Reactions. , 2018, Chemistry.

[12]  W. Zi,et al.  Transition-metal catalyzed enantioselective hydrofunctionalization of alkynes , 2018, Tetrahedron Letters.

[13]  Wenlong Wang,et al.  Reusable N-Heterocyclic Carbene Complex Catalysts and Beyond: A Perspective on Recycling Strategies. , 2018, Chemical reviews.

[14]  C. Vidal,et al.  Concurrent and orthogonal gold(I) and ruthenium(II) catalysis inside living cells , 2018, Nature Communications.

[15]  P. Mukherjee,et al.  Chemical Transformations in Confined Space of Coordination Architectures. , 2018, Inorganic chemistry.

[16]  N. Endo,et al.  Rational Design of a Metallocatalytic Cavitand for Regioselective Hydration of Specific Alkynes , 2018 .

[17]  Peng‐Fei Xu,et al.  Catalytic Organic Reactions in Water toward Sustainable Society. , 2017, Chemical reviews.

[18]  V. Cadierno,et al.  Metal-Catalyzed Intra- and Intermolecular Addition of Carboxylic Acids to Alkynes in Aqueous Media: A Review , 2017 .

[19]  V. Dufaud,et al.  Sulfoxidation inside A C3-Vanadium(V) Bowl-Shaped Catalyst , 2017 .

[20]  Yongming Zhang,et al.  Cyclodextrin Cavity-Induced Mechanistic Switch in Copper-Catalyzed Hydroboration. , 2017, Angewandte Chemie.

[21]  Yongming Zhang,et al.  Artificial Chiral Metallo-pockets Including a Single Metal Serving as Structural Probe and Catalytic Center , 2017 .

[22]  H. Onoe,et al.  In Vivo Gold Complex Catalysis within Live Mice. , 2017, Angewandte Chemie.

[23]  Junliang Zhang,et al.  Gold-Catalyzed Enantioselective Annulations. , 2017, Chemistry.

[24]  L. Toupet,et al.  Substrate‐Selective Olefin Hydrogenation with a Cavitand‐Based Bis(N‐anisyl iminophosphorane) , 2017 .

[25]  R. Gust,et al.  Update on metal N-heterocyclic carbene complexes as potential anti-tumor metallodrugs , 2016 .

[26]  D. Astruc,et al.  Supramolecular nanoreactors for catalysis , 2016 .

[27]  R. Pleixats,et al.  Sol–Gel Immobilized N‐Heterocyclic Carbene Gold Complex as a Recyclable Catalyst for the Rearrangement of Allylic Esters and the Cycloisomerization of γ‐Alkynoic Acids , 2016 .

[28]  S. Nolan,et al.  A Switchable Gold Catalyst by Encapsulation in a Self‐Assembled Cage , 2016, Chemistry.

[29]  M. Otte.  Size-Selective Molecular Flasks , 2016 .

[30]  F. Dean Toste,et al.  Recent advances in enantioselective gold catalysis. , 2016, Chemical Society reviews.

[31]  J. Rebek,et al.  Cavitands as Reaction Vessels and Blocking Groups for Selective Reactions in Water. , 2016, Angewandte Chemie.

[32]  J. Rebek,et al.  Cavitands as Chaperones for Monofunctional and Ring-Forming Reactions in Water. , 2016, Journal of the American Chemical Society.

[33]  J. Reek,et al.  A Self-Assembled Molecular Cage for Substrate-Selective Epoxidation Reactions in Aqueous Media , 2016 .

[34]  A. Gautier,et al.  Water-Soluble Gold–N-Heterocyclic Carbene Complexes for the Catalytic Homogeneous Acid- and Silver-Free Hydration of Hydrophilic Alkynes. , 2015 .

[35]  X. Bi,et al.  Silver-catalysed reactions of alkynes: recent advances. , 2015, Chemical Society reviews.

[36]  G. Hammond,et al.  Revisiting the Influence of Silver in Cationic Gold Catalysis: A Practical Guide. , 2015, Organic letters.

[37]  N. Krause,et al.  Smaller, faster, better: modular synthesis of unsymmetrical ammonium salt-tagged NHC-gold(I) complexes and their application as recyclable catalysts in water. , 2015, Organic & biomolecular chemistry.

[38]  C. Diesendruck,et al.  Water in N-heterocyclic carbene-assisted catalysis. , 2015, Chemical reviews.

[39]  O. Reinaud,et al.  Supramolecular control of transition metal complexes in water by a hydrophobic cavity: a bio-inspired strategy. , 2015, Organic & biomolecular chemistry.

[40]  J. Reek,et al.  Enantioselective hydroformylation by a Rh-catalyst entrapped in a supramolecular metallocage. , 2015, Journal of the American Chemical Society.

[41]  O. Reinaud,et al.  Biomimetic cavity-based metal complexes. , 2015, Chemical Society reviews.

[42]  J. Reek,et al.  Transition metal catalysis in confined spaces. , 2015, Chemical Society reviews.

[43]  O. Staszewska-Krajewska,et al.  Diastereoselective synthesis of propargylic N-hydroxylamines via NHC-copper(I) halide-catalyzed reaction of terminal alkynes with chiral nitrones on water. , 2015, Chemical communications.

[44]  N. Krause,et al.  Ammonium‐Salt‐Tagged IMesAuCl Complexes and Their Application in Gold‐Catalyzed Cycloisomerization Reactions in Water , 2015 .

[45]  Daniel J. Lippincott,et al.  Asymmetric gold-catalyzed lactonizations in water at room temperature. , 2014, Angewandte Chemie.

[46]  J. Reek,et al.  Encapsulated cobalt-porphyrin as a catalyst for size-selective radical-type cyclopropanation reactions. , 2014, Chemistry.

[47]  M. Maier,et al.  The mechanism of gold(I)-catalyzed hydroalkoxylation of alkynes: an extensive experimental study. , 2014, Chemistry.

[48]  Piet W N M van Leeuwen,et al.  Supramolecular catalysis. Part 2: artificial enzyme mimics. , 2014, Chemical Society reviews.

[49]  P. Ballester,et al.  Supramolecular catalysis. Part 1: non-covalent interactions as a tool for building and modifying homogeneous catalysts. , 2014, Chemical Society reviews.

[50]  C. Müller,et al.  Recent Advances in Molecular Recognition in Water: Artificial Receptors and Supramolecular Catalysis , 2014 .

[51]  P. Besenius,et al.  Water-Soluble Au(I) Complexes, Their Synthesis and Applications , 2013 .

[52]  J. Borge,et al.  Water-Soluble Gold(I) and Gold(III) Complexes with Sulfonated N-Heterocyclic Carbene Ligands: Synthesis, Characterization, and Application in the Catalytic Cycloisomerization of γ-Alkynoic Acids into Enol-Lactones , 2013 .

[53]  J. Reek,et al.  Substrate selectivity in the alkyne hydration mediated by NHC–Au(I) controlled by encapsulation of the catalyst within a hydrogen bonded hexameric host , 2013 .

[54]  C. Amatore,et al.  NHC-capped cyclodextrins (ICyDs): insulated metal complexes, commutable multicoordination sphere, and cavity-dependent catalysis. , 2013, Angewandte Chemie.

[55]  J. C. Flores,et al.  Sulfonated Water-Soluble N-Heterocyclic Carbene Silver(I) Complexes: Behavior in Aqueous Medium and as NHC-Transfer Agents to Platinum(II) , 2013 .

[56]  R. Rubbiani,et al.  N-Heterocyclic carbene metal complexes in medicinal chemistry. , 2013, Dalton transactions.

[57]  Rafael Gramage‐Doria,et al.  Metallated cavitands (calixarenes, resorcinarenes, cyclodextrins) with internal coordination sites , 2013 .

[58]  Fritz E. Kühn,et al.  Synthese und Anwendung wasserlöslicher NHC‐Übergangsmetall‐Komplexe , 2013 .

[59]  W. Herrmann,et al.  Synthesis and application of water-soluble NHC transition-metal complexes. , 2013, Angewandte Chemie.

[60]  F. Verpoort,et al.  N-Heterocyclic carbene transition metal complexes for catalysis in aqueous media. , 2012, Chemical Society reviews.

[61]  D. Sames,et al.  Catalytic coupling of arene C-H bonds and alkynes for the synthesis of coumarins: substrate scope and application to the development of neuroimaging agents. , 2012, The Journal of organic chemistry.

[62]  Xingbo Liu,et al.  "Silver effect" in gold(I) catalysis: an overlooked important factor. , 2012, Journal of the American Chemical Society.

[63]  P. S. Prasad,et al.  Solvent-free hydration of alkynes over a heterogeneous silver exchanged silicotungstic acid catalyst , 2012 .

[64]  S. Conejero,et al.  Cycloisomerization versus hydration reactions in aqueous media: a Au(III)-NHC catalyst that makes the difference. , 2012, Organic letters.

[65]  A. Gautier,et al.  A water soluble Cu(I)-NHC for CuAAC ligation of unprotected peptides under open air conditions. , 2012, Chemical communications.

[66]  Daniel A. Turner,et al.  Design, preparation, and study of catalytic gated baskets. , 2012, The Journal of organic chemistry.

[67]  M. Fujita,et al.  Cage-catalyzed Knoevenagel condensation under neutral conditions in water. , 2012, Journal of the American Chemical Society.

[68]  Wenlong Wang,et al.  Reusable ammonium salt-tagged NHC–Cu(I) complexes: preparation and catalytic application in the three component click reaction , 2011 .

[69]  S. Aoki,et al.  Selective hydrolysis of phosphate monoester by a supramolecular phosphatase formed by the self-assembly of a bis(Zn(2+)-cyclen) complex, cyanuric acid, and copper in an aqueous solution (cyclen = 1,4,7,10-tetraazacyclododecane). , 2011, Inorganic chemistry.

[70]  P. Toullec,et al.  Asymmetric Au-catalyzed domino cyclization/nucleophile addition reactions of enynes in the presence of water, methanol and electron-rich aromatic derivatives , 2011 .

[71]  Z Jane Wang,et al.  Hydroalkoxylation catalyzed by a gold(I) complex encapsulated in a supramolecular host. , 2011, Journal of the American Chemical Society.

[72]  F. Joó,et al.  Water-soluble gold(I)-NHC complexes of sulfonated IMes and SIMes and their catalytic activity in hydration of alkynes , 2011 .

[73]  W. Goddard,et al.  Phosphoramidite gold(I)-catalyzed diastereo- and enantioselective synthesis of 3,4-substituted pyrrolidines. , 2011, Journal of the American Chemical Society.

[74]  Chao‐Jun Li,et al.  “On water”-promoted direct alkynylation of isatins catalyzed by NHC–silver complexes for the efficient synthesis of 3-hydroxy-3-ethynylindolin-2-ones , 2011 .

[75]  S. Nolan.  The development and catalytic uses of N-heterocyclic carbene gold complexes. , 2011, Accounts of chemical research.

[76]  J. Reek,et al.  Supramolecular control on chemo- and regioselectivity via encapsulation of (NHC)-Au catalyst within a hexameric self-assembled host. , 2011, Journal of the American Chemical Society.

[77]  S. Nolan,et al.  Efficient silver-free gold(I)-catalyzed hydration of alkynes at low catalyst loading , 2011 .

[78]  F. Joó,et al.  Novel Sulfonated N-Heterocyclic Carbene Gold(I) Complexes: Homogeneous Gold Catalysis for the Hydration of Terminal Alkynes in Aqueous Media , 2010 .

[79]  E. Zaborova,et al.  μ-Waves avoid large excesses of diisobutylaluminium-hydride (DIBAL-H) in the debenzylation of perbenzylated α-cyclodextrin , 2010 .

[80]  Juyoung Yoon,et al.  A rationally designed fluorescence turn-on probe for the gold(III) ion. , 2010, Organic letters.

[81]  C. Winter,et al.  Towards sustainable homogeneous gold catalysis: cycloisomerization of functionalized allenes in water , 2009 .

[82]  K. Jitsukawa,et al.  Supported silver nanoparticle catalyst for selective hydration of nitriles to amides in water. , 2009, Chemical communications.

[83]  Michito Yoshizawa,et al.  Funktionale molekulare Reaktionskolben: neuartige Eigenschaften und Reaktionen in diskreten, selbstorganisierten Wirtmolekülen , 2009 .

[84]  M. Fujita,et al.  Functional molecular flasks: new properties and reactions within discrete, self-assembled hosts. , 2009, Angewandte Chemie.

[85]  P. Toullec,et al.  Towards asymmetric Au-catalyzed hydroxy- and alkoxycyclization of 1,6-enynes , 2009 .

[86]  S. Nolan,et al.  [(NHC)Au(I)]-catalyzed acid-free alkyne hydration at part-per-million catalyst loadings. , 2009, Journal of the American Chemical Society.

[87]  M. Sollogoub,et al.  Multiple homo- and hetero-functionalizations of alpha-cyclodextrin through oriented deprotections. , 2008, The Journal of organic chemistry.

[88]  Yuanhong Liu,et al.  Gold-catalyzed multicomponent synthesis of aminoindolizines from aldehydes, amines, and alkynes under solvent-free conditions or in water. , 2007, Organic letters.

[89]  A Stephen K Hashmi,et al.  Gold-catalyzed organic reactions. , 2007, Chemical reviews.

[90]  L. Cavallo,et al.  (NHC)Copper(I)-catalyzed [3+2] cycloaddition of azides and mono- or disubstituted alkynes. , 2006, Chemistry.

[91]  Matthew S. Anderson,et al.  Synthesis and Characterization of Water-Soluble Silver and Palladium Imidazol-2-ylidene Complexes with Noncoordinating Anionic Substituents , 2006 .

[92]  Chao‐Jun Li,et al.  Diastereoselective Synthesis of α‐Oxyamines via Gold‐, Silver‐ and Copper‐Catalyzed, Three‐Component Couplings of α‐Oxyaldehydes, Alkynes, and Amines in Water , 2006 .

[93]  M. Reetz,et al.  Copper-phthalocyanine conjugates of serum albumins as enantioselective catalysts in Diels-Alder reactions. , 2006, Angewandte Chemie.

[94]  P. Toullec,et al.  Room temperature Au(I)-catalyzed exo-selective cycloisomerization of acetylenic acids: an entry to functionalized gamma-lactones. , 2006, Journal of the American Chemical Society.

[95]  M. Sollogoub,et al.  Triisobutylaluminium and diisobutylaluminium hydride as molecular scalpels: the regioselective stripping of perbenzylated sugars and cyclodextrins. , 2004, Chemistry.

[96]  C. Wesdemiotis,et al.  Formation of water-soluble pincer silver(I)-carbene complexes: a novel antimicrobial agent. , 2004, Journal of medicinal chemistry.

[97]  J. Mallet,et al.  An efficient preparation of 6I, IV dihydroxy permethylated β-cyclodextrin , 2003 .

[98]  Chao‐Jun Li,et al.  A highly efficient three-component coupling of aldehyde, alkyne, and amines via C-H activation catalyzed by gold in water. , 2003, Journal of the American Chemical Society.

[99]  S. Schneider,et al.  Synthesis of the First Gold(I) Carbene Complex with a Gold‐Oxygen Bond — First Catalytic Application of Gold(I) Complexes Bearing N‐Heterocyclic Carbenes , 2003 .

[100]  Kazuhiko Sato,et al.  Highly efficient AuI-catalyzed hydration of alkynes. , 2002, Angewandte Chemie.

[101]  S. Nguyen,et al.  Artificial Enzymes Formed through Directed Assembly of Molecular Square Encapsulated Epoxidation Catalysts. , 2001, Angewandte Chemie.

[102]  F. Stelzer,et al.  Platinum-catalyzed cycloisomerization reactions of enynes. , 2001, Journal of the American Chemical Society.