Mechanistic switch in dual gold catalysis of diynes: C(sp(3))-H activation through bifurcation--vinylidene versus carbene pathways.

The other side of the mountain: Changing the framework of diyne systems opens up new cyclization modes for dual gold catalysis. Instead of a 5-endo cyclization and gold vinylidenes a 6-endo cyclization gives rise to gold-stabilized carbenes as key intermediates for selective C-H insertions.

[1]  F. Rominger,et al.  Dual gold catalysis: σ,π-propyne acetylide and hydroxyl-bridged digold complexes as easy-to-prepare and easy-to-handle precatalysts. , 2013, Chemistry.

[2]  F. Rominger,et al.  Vinylidengoldverbindungen: intermolekulare C(sp3)‐H‐Insertionen und Cyclopropanierungspfade , 2012 .

[3]  F. Rominger,et al.  Gold vinylidene complexes: intermolecular C(sp3)-H insertions and cyclopropanations pathways. , 2012, Angewandte Chemie.

[4]  Miguel A. Rodríguez,et al.  Gold-catalyzed functionalization of unactivated C(sp3)-H bonds by hydride transfer facilitated by alkynylspirocyclopropanes. , 2012, Angewandte Chemie.

[5]  Steven P. Nolan,et al.  Katalyse mit zweikernigen Goldkomplexen: Sind zwei Goldzentren besser als eines? , 2012 .

[6]  S. Nolan,et al.  Dinuclear gold catalysis: are two gold centers better than one? , 2012, Angewandte Chemie.

[7]  N. Fujii,et al.  Gold(I)-catalyzed regioselective inter-/intramolecular addition cascade of di- and triynes for direct construction of substituted naphthalenes. , 2012, The Journal of organic chemistry.

[8]  F. Rominger,et al.  Eine einfache Gold‐katalysierte Synthese von Benzofulvenen – gem‐diaurierte Spezies als “Instant‐Dual‐Activation”‐Präkatalysatoren , 2012 .

[9]  F. Rominger,et al.  Simple gold-catalyzed synthesis of benzofulvenes--gem-diaurated species as "instant dual-activation" precatalysts. , 2012, Angewandte Chemie.

[10]  Rai‐Shung Liu,et al.  Gold-catalyzed oxidative cyclizations of cis-3-en-1-ynes to form cyclopentenone derivatives. , 2012, Angewandte Chemie.

[11]  M. R. Gagné,et al.  Strong electronic and counterion effects on geminal digold formation and reactivity as revealed by gold(I)-aryl model complexes. , 2012, Angewandte Chemie.

[12]  F. Rominger,et al.  Gold‐Catalyzed Synthesis of Dibenzopentalenes – Evidence for Gold Vinylidenes , 2012 .

[13]  A. Hashmi,et al.  Gold catalysis in total synthesis--an update. , 2012, Chemical Society reviews.

[14]  Abdullah M. Asiri,et al.  Synthesis of new donor–acceptor–donor materials via Au-catalyzed double cascade cyclization , 2012 .

[15]  M. White.  Adding Aliphatic C–H Bond Oxidations to Synthesis , 2012, Science.

[16]  F. Rominger,et al.  The Role of Gold Acetylides as a Selectivity Trigger and the Importance of gem-Diaurated Species in the Gold-Catalyzed Hydroarylating-Aromatization of Arene-Diynes , 2012 .

[17]  Liming Zhang,et al.  Experimental and computational evidence for gold vinylidenes: generation from terminal alkynes via a bifurcation pathway and facile C-H insertions. , 2012, Journal of the American Chemical Society.

[18]  J. Tabet,et al.  Tracking gold acetylides in gold(I)-catalyzed cycloisomerization reactions of enynes , 2011 .

[19]  A. Corma,et al.  Intermolecular [2 + 2] Cycloaddition of Alkyne-Alkene Catalyzed by Au(I) Complexes. What Are the Catalytic Sites Involved? , 2011 .

[20]  R. Widenhoefer,et al.  Cationic Gold(I) π-Complexes of Terminal Alkynes and Their Conversion to Dinuclear σ,π-Acetylide Complexes , 2011 .

[21]  N. Fujii,et al.  Gold(I)-catalyzed polycyclizations of polyenyne-type anilines based on hydroamination and consecutive hydroarylation cascade. , 2011, The Journal of organic chemistry.

[22]  J. Xiao,et al.  Gold-α-Oxocarbenoide in der katalysierten Übertragung von Sauerstoffatomen auf Alkine , 2011 .

[23]  Xingwei Li,et al.  Gold α-oxo carbenoids in catalysis: catalytic oxygen-atom transfer to alkynes. , 2011, Angewandte Chemie.

[24]  F. Gagosz,et al.  Gold and Brønsted acid catalyzed hydride shift onto allenes: divergence in product selectivity. , 2011, Journal of the American Chemical Society.

[25]  K. Houk,et al.  Selective gold(I)-catalyzed formation of tetracyclic indolines: a single transition structure and bifurcations lead to multiple products. , 2011, The Journal of organic chemistry.

[26]  Phil S. Baran,et al.  C-H functionalization logic in total synthesis. , 2011, Chemical Society reviews.

[27]  A. Corma,et al.  Gold-catalyzed carbon-heteroatom bond-forming reactions. , 2011, Chemical reviews.

[28]  W. Goddard,et al.  Mechanistic study of gold(I)-catalyzed intermolecular hydroamination of allenes. , 2010, Journal of the American Chemical Society.

[29]  F. Gagosz,et al.  Gold(I)-catalyzed rearrangement of propargyl benzyl ethers: a practical method for the generation and in situ transformation of substituted allenes. , 2010, Journal of the American Chemical Society.

[30]  C. Nevado,et al.  Mechanistic insights in gold-stabilized nonclassical carbocations: gold-catalyzed rearrangement of 3-cyclopropyl propargylic acetates. , 2010, Journal of the American Chemical Society.

[31]  Igor D. Jurberg,et al.  Hydroalkylation of alkynyl ethers via a gold(I)-catalyzed 1,5-hydride shift/cyclization sequence. , 2010, Journal of the American Chemical Society.

[32]  N. Fujii,et al.  Gold‐Catalyzed Intramolecular Alkyne Cycloisomerization Cascade: Direct Synthesis of Aryl‐Annulated[a]carbazoles from Aniline‐Substituted Diethynylarenes , 2010 .

[33]  Melanie S Sanford,et al.  Palladium-catalyzed ligand-directed C-H functionalization reactions. , 2010, Chemical reviews.

[34]  Y. Liu,et al.  Asymmetrical fluorene[2,3-b]benzo[d]thiophene derivatives: synthesis, solid-state structures, and application in solution-processable organic light-emitting diodes. , 2009, Chemistry.

[35]  X. Chen,et al.  Palladium(II)‐katalysierte C‐H‐Aktivierung/C‐C‐Kreuzkupplung: Vielseitigkeit und Anwendbarkeit , 2009 .

[36]  jin-quan yu,et al.  Palladium(II)-catalyzed C-H activation/C-C cross-coupling reactions: versatility and practicality. , 2009, Angewandte Chemie.

[37]  Rai‐Shung Liu,et al.  Gold-catalyzed 1,3-addition of a sp3-hybridized C-H bond to alkenylcarbenoid intermediate. , 2008, Journal of the American Chemical Society.

[38]  K. N. Houk,et al.  Bifurkationen auf den Potentialenergiehyperflächen organischer Reaktionen , 2008 .

[39]  Lai Xu,et al.  Bifurcations on potential energy surfaces of organic reactions. , 2008, Angewandte Chemie.

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

[41]  A. Arcadi.  Alternative synthetic methods through new developments in catalysis by gold. , 2008, Chemical reviews.

[42]  Zigang Li,et al.  Gold-catalyzed organic transformations. , 2008, Chemical reviews.

[43]  D. Hashizume,et al.  Photoluminescent properties and molecular structures of [NaphAu(PPh(3))] and [mu-Naph {Au(PPh(3))}(2)] ClO(4) (Naph = 2-naphthyl). , 2008, Dalton transactions.

[44]  Kazuo Takimiya,et al.  Synthesis, properties, and structures of benzo[1,2-b:4,5-b']bis[b]benzothiophene and benzo[1,2-b:4,5-b']bis[b]benzoselenophene. , 2007, Organic letters.

[45]  A. S. K. Hashmi,et al.  Goldkatalysierte benzylische C‐H‐Aktivierung bei Raumtemperatur , 2007 .

[46]  A. Hashmi,et al.  Gold-catalyzed benzylic C-H activation at room temperature. , 2007, Angewandte Chemie.

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

[48]  Alois Fürstner,et al.  Katalytische carbophile Aktivierung: Platin‐ und Gold‐π‐Säuren als Katalysatoren , 2007 .

[49]  Alois Fürstner,et al.  Catalytic carbophilic activation: catalysis by platinum and gold pi acids. , 2007, Angewandte Chemie.

[50]  Mark E. Scott,et al.  Aryl-aryl bond formation by transition-metal-catalyzed direct arylation. , 2007, Chemical reviews.

[51]  V. Gandon,et al.  Gold(I)- and gold(III)-catalyzed cycloisomerization of allenynes: a remarkable halide effect. , 2006, Angewandte Chemie.

[52]  K. Godula,et al.  C-H Bond Functionalization in Complex Organic Synthesis , 2006, Science.

[53]  Ying Ran,et al.  Platinum-catalyzed aromatization of enediynes via a C-H bond insertion of tethered alkanes. , 2006, Organic letters.

[54]  Rai‐Shung Liu,et al.  Regioselective haloaromatization of 1,2-bis(ethynyl)benzene via halogen acids and PtCl2. Platinum-catalyzed 6-pi electrocyclization of 1,2-bis(1'-haloethenyl)benzene intermediates. , 2005, The Journal of organic chemistry.

[55]  Ying Ran,et al.  Ruthenium-catalyzed aromatization of enediynes via highly regioselective nucleophilic additions on a pi-alkyne functionality. A useful method for the synthesis of functionalized benzene derivatives. , 2005, Journal of the American Chemical Society.

[56]  K. Ohe,et al.  Rhodium(I)‐Catalyzed Cycloaromatization of Acyclic 3‐Ene‐1,5‐diynes , 1996 .

[57]  Kouichi Ohe,et al.  RhI-katalysierte Cycloaromatisierung acyclischer 3-En-1,5-diine† , 1996 .

[58]  Barry M. Trost,et al.  Atom Economy—A Challenge for Organic Synthesis: Homogeneous Catalysis Leads the Way , 1995 .

[59]  B. M. Trost.  Atomökonomische Synthesen – eine Herausforderung in der Organischen Chemie: die Homogenkatalyse als wegweisende Methode , 1995 .