Gold-catalyzed organic reactions.

Although homogeneous gold catalysis was known previously, an exponential growth was only induced 12 years ago. The key findings which induce that rise of the field are discussed. This includes early reactions of allenes and furanynes and intermediates of these conversions as well as hydroarylation reactions. Other substrate types addressed are alkynyl epoxides and N-propargyl carboxamides. Important vinylgold intermediates, the transmetalation from gold to other transition metals, the development of new ligands for gold catalysis, and significant contributions from computational chemistry are other crucial points for the field highlighted here.

[1]  Lei Wang,et al.  Gold(I) Iodide Catalyzed Sonogashira Reactions , 2008 .

[2]  W. Frey,et al.  Gold‐Katalyse: Nachweis von Arenoxiden als Zwischenstufen der Phenol‐Synthese , 2005 .

[3]  Rai‐Shung Liu,et al.  Diversity in gold- and silver-catalyzed cycloisomerization of epoxide-alkyne functionalities. , 2008, Organic letters.

[4]  F Dean Toste,et al.  Ligand effects in homogeneous Au catalysis. , 2008, Chemical reviews.

[5]  A. Hashmi,et al.  Gold Catalysis: Alkylideneoxazolines and ‐oxazoles from Intramolecular Hydroamination of an Alkyne by a Trichloroacetimidate , 2006 .

[6]  J. W. Bats,et al.  Die erste und hochdiastereoselektive Synthese von Palladepanen , 1999 .

[7]  A. S. K. Hashmi,et al.  Gold-Katalyse: die Vorteile von N- und N,O-Liganden† , 2004 .

[8]  A. Hashmi,et al.  Gold-Catalyzed Cyclization of N-Alkynyl Carbamates , 2007 .

[9]  A. Hashmi,et al.  The Condensation of Carbonyl Compounds with Electron-Rich Arenes: Mercury, Thallium, Gold or a Proton? , 2006 .

[10]  A. S. K. Hashmi,et al.  Übergangsmetallkatalysierte Dimerisierung von Allenylketonen , 1995 .

[11]  J. Bats,et al.  Gold Catalysis: First Applications of Cationic Binuclear Gold(I) Complexes and the First Intermolecular Reaction of an Alkyne with a Furan , 2006 .

[12]  A. Stephen K. Hashmi,et al.  Highly Selective Gold-Catalyzed Arene Synthesis , 2000 .

[13]  J. H. Teles,et al.  Kationische Gold(I)‐Komplexe: hocheffiziente Katalysatoren für die Addition von Alkoholen an Alkine , 1998 .

[14]  Alan E. Comyns Let them eat cake , 2002 .

[15]  G. Hutchings A golden future for green chemistry , 2007 .

[16]  A. Hashmi,et al.  Gold catalysis: five new bonds by a domino hydroarylation/cycloisomerization , 2005 .

[17]  J. Bats,et al.  Gold Catalysis: Oxepines from γ‐Alkynylfurans , 2007 .

[18]  M. Sawamura,et al.  Catalytic asymmetric aldol reaction: reaction of aldehydes with isocyanoacetate catalyzed by a chiral ferrocenylphosphine-gold(I) complex , 1986 .

[19]  A. Meijere,et al.  Gold catalysed rearrangements of strained small ring hydrocarbons , 1976 .

[20]  J. Bats,et al.  C-C-Bond Formation by the Palladium-Catalyzed Cycloisomerization/Dimerization of Terminal Allenyl Ketones: Selectivity and Mechanistic Aspects. , 1997, The Journal of organic chemistry.

[21]  J. Bats,et al.  SYNTHESIS OF ALLENYL KETONES AND THEIR PALLADIUM-CATALYZED CYCLOISOMERIZATION/DIMERIZATION : APPROACHING THE LIMITS , 1999 .

[22]  F. Gasparrini,et al.  Gold(III) catalyzed oxidation of sulfides to sulfoxides by nitric acid under phase-transfer conditions: a new synthesis of sulfoxides , 1983 .

[23]  B. Martín‐Matute,et al.  PtII‐Catalyzed Intramolecular Reaction of Furans with Alkynes , 2001 .

[24]  K. Utimoto,et al.  Preparation of 2,3,4,5-Tetrahydropyridines from 5-Alkynylamines Under the Catalytic Action of Gold(III) Salts , 1987 .

[25]  B. Martín‐Matute,et al.  Intramolecular reactions of alkynes with furans and electron rich arenes catalyzed by PtCl2: the role of platinum carbenes as intermediates. , 2003, Journal of the American Chemical Society.

[26]  A. Hashmi,et al.  Gold(III) Chloride-Catalyzed Addition Reactions of Electron-Rich Arenes to Methyl Vinyl Ketone , 2003 .

[27]  A. Hashmi,et al.  Gold Catalysis: Mild Conditions for the Transformation of Alkynyl Epoxides to Furans , 2004 .

[28]  A. Hashmi,et al.  Gold Catalysis: Dihydroisobenzofurans and Isochromanes by the Intramolecular Furan/Alkyne Reaction , 2006 .

[29]  A. Togni,et al.  Chiral cooperativity: the nature of the diastereoselective and enantioselective step in the gold(I)-catalyzed aldol reaction utilizing chiral ferrocenylamine ligands , 1990 .

[30]  A. Hashmi,et al.  Gold Catalysis: Observation of a Two‐Fold Intermolecular Hydroarylation of Unactivated C–C Triple Bonds , 2006 .

[31]  Alan E. Comyns This precious bane , 2004 .

[32]  Wolfgang Frey,et al.  Gold catalysis: mild conditions for the synthesis of oxazoles from N-propargylcarboxamides and mechanistic aspects. , 2004, Organic letters.

[33]  A. Corma,et al.  Catalysis by gold(I) and gold(III): a parallelism between homo- and heterogeneous catalysts for copper-free Sonogashira cross-coupling reactions. , 2007, Angewandte Chemie.

[34]  A. S. K. Hashmi,et al.  Eine neue Gold‐katalysierte C‐C‐Bindungsknüpfung , 2000 .

[35]  Christian Bruneau Elektrophile Aktivierung und Cycloisomerisierung von Eninen: ein Weg zu funktionalen Cyclopropanen , 2005 .

[36]  Hajime Ito,et al.  First gold complex-catalysed selective hydrosilylation of organic compounds , 2000 .

[37]  Alan E. Comyns BIOTECHNOLOGY EVOLVING — BUT SLOWLY , 2002 .

[38]  J. W. Bats,et al.  Herstellung enantiomerenreiner 5‐Palladatricyclo[4.1.0.02,4]heptane und deren Umsetzung zu enantiomerenreinen, helical chiralen Pd‐Komplexen , 1997 .

[39]  J. Teles,et al.  Cationic Gold(I) Complexes: Highly Efficient Catalysts for the Addition of Alcohols to Alkynes. , 1998, Angewandte Chemie.

[40]  M. Chiarini,et al.  Sequential alkylation/transition metal catalysed annulation reactions of 1,3-dicarbonyl compounds with propargyl bromide , 2000 .

[41]  J. Bats,et al.  Gold catalysis: deuterated substrates as the key for an experimental insight into the mechanism and selectivity of the phenol synthesis. , 2008, Chemistry.

[42]  A. Hashmi,et al.  Asymmetric Synthesis of Palladacycles by Regioselective Oxidative Cyclization of C2-Symmetrical, Chiral Alkenes and Determination of the Configuration of All Stereocenters , 1998 .

[43]  R. Hoffmann Brücken zwischen Anorganischer und Organischer Chemie (Nobel‐Vortrag) , 2006 .

[44]  A. Corma,et al.  Heterogeneous Gold‐Catalysed Synthesis of Phenols , 2006 .

[45]  J. Bats,et al.  Gold catalysis: on the phenol synthesis. , 2001, Organic letters.

[46]  Shichao Yu,et al.  Goldkatalysierte Cyclisierung von Eninen , 2006 .

[47]  C. Nevado,et al.  Non-stabilized transition metal carbenes as intermediates in intramolecular reactions of alkynes with alkenes. , 2004, Chemical Society reviews.

[48]  K. Utimoto,et al.  Effective transformation of unactivated alkynes into ketones or acetals with a gold(III) catalyst , 1991 .

[49]  A. Corma,et al.  New Heterogenized Gold(I)‐Heterocyclic Carbene Complexes as Reusable Catalysts in Hydrogenation and Cross‐Coupling Reactions , 2006 .

[50]  K. Utimoto,et al.  Efficient Transformation of Methyl Propargyl Ethers into α,β-Unsaturated Ketones , 1991 .

[51]  J. Bats,et al.  Gold catalysis: efficient synthesis and structural assignment of jungianol and epi-jungianol. , 2003, Chemistry.

[52]  A. Hashmi,et al.  Mercury(II)-catalyzed synthesis of spiro[4.5]decatrienediones in the presence of water , 1998 .

[53]  I. Ojima,et al.  Catalytic Asymmetric Synthesis , 1993 .

[54]  J. Bats,et al.  Mercury(II)‐Catalyzed Synthesis of Spiro[4.5]decatrienediones from Allenyl Ketones and Comparison with Silver(I)‐, Palladium(II)‐ and Brønsted Acid‐Catalyzed Reactions , 2000 .

[55]  K. Ohe,et al.  Ruthenium-catalyzed cyclopropanation of alkenes using propargylic carboxylates as precursors of vinylcarbenoids. , 2003, The Journal of organic chemistry.

[56]  K. Ohe,et al.  A new ruthenium-catalyzed cyclopropanation of alkenes using propargylic acetates as a precursor of vinylcarbenoids , 2003 .

[57]  A. Hashmi,et al.  Switch from Palladium-Catalyzed Cycloisomerization/Dimerization of Terminal Allenyl Ketones to Preferential Formation of Monomers by a 5-Palladatricyclo[4.1.0.02,4]heptane Catalyst: Synthesis of Furans from Substrates Incompatible with the Commonly Used Silver Catalysts , 1997 .

[58]  A. Hashmi,et al.  Gold catalysis: no steric limitations in the phenol synthesis. , 2006, Chemistry.

[59]  P. G. Gassman,et al.  Transition Metal Complex Promoted Rearrangements. The Effect of the Metal and of the Attached Ligands on the Mode of Cleavage of Methylated Bicyclo[1.1.0]butanes , 1972 .

[60]  J. Bats,et al.  Gold Catalysis: Evidence for the In‐situ Reduction of Gold(III) During the Cyclization of Allenyl Carbinols , 2006 .

[61]  J. Bats,et al.  Gold Catalysis: Synthesis of 3-Acylindenes from 2-Alkynylaryl Epoxides , 2008 .