Pyrrole Formation via Reactivity of η4-(Vinylketenimine)iron Complexes with Electron-Deficient Alkynes

: When electron-deficient alkynes reacted with η 4 -(vinylketenimine)iron complexes, pyrroles were produced. Pyrrole formation involved the [2+3] cycloaddition of alkyne to the ketenimine moiety, migration of the vinyl group, and decomplexation. Either alkynes bearing two electron-withdrawing groups, or terminal alkynes with an electron-withdrawing group reacted to generate pyrroles.

[1]  T. Hudlický,et al.  Synthesis of Nororipavine and Noroxymorphone via N- and O-Demethylation of Iron Tricarbonyl Complex of Thebaine , 2016, Synthesis.

[2]  W. A. Donaldson,et al.  Reactivity of acyclic (pentadienyl)iron(1+) cations with phosphonate stabilized nucleophiles: application to the synthesis of oxygenated metabolites of carvone , 2016 .

[3]  Monika Ali Khan,et al.  Tricarbonyliron(0) complexes of bio-derived η4 cyclohexadiene ligands: An approach to analogues of oseltamivir , 2015 .

[4]  A. J. Pearson,et al.  Stereocontrolled Intramolecular Iron-Mediated Tandem [6 + 2]-Ene-Type Diene/Dienol Ether Double Cyclization Reactions. , 2015 .

[5]  A. J. Pearson,et al.  Stereocontrolled intramolecular iron-mediated tandem [6+2]-ene-type diene/dienol ether double cyclization reactions , 2015 .

[6]  T. Okauchi,et al.  Unprecedented formation of η(4)-(vinylketene)iron complexes from η(4)-(diene)iron complexes and aromatic compounds in the presence of a Lewis acid. , 2015, Chemical communications.

[7]  R. Toscano,et al.  An expedient approach to synthesize fluorescent 3-substituted 4H-quinolizin-4-ones via (η(4)-vinylketene)-Fe(CO)3 complexes. , 2015, Dalton transactions.

[8]  K. Aoki,et al.  Corrigendum to “Application of iron carbonyl complexation to the selective total synthesis of sanshools” [Tetrahedron Lett. 53 (2012) 6000–6003] , 2013 .

[9]  K. Aoki,et al.  Application of iron carbonyl complexation to the selective total synthesis of sanshools , 2012 .

[10]  C. Anson,et al.  Stereochemical requirements of oxidative cyclizations in extended iterative organoiron-mediated routes to alkaloids. , 2012, The Journal of organic chemistry.

[11]  Emma L. Pearson,et al.  On the Diels-Alder dimerisation of cross-conjugated trienes. , 2012, Chemical communications.

[12]  H. Knölker,et al.  TRANSITION METALS IN ORGANIC SYNTHESIS, PART 104. IRON-MEDIATED TOTAL SYNTHESIS OF FUROCLAUSINE-A , 2012 .

[13]  R. S. Paley Iron: Organometallic Chemistry , 2011 .

[14]  F. Cortés‐Guzmán,et al.  Iron(0) promotes aza cyclization of an elusive ferrocenylketene , 2011 .

[15]  R. Pike,et al.  Diastereoselective spiroketalization: stereocontrol using an iron(0) tricarbonyl diene complex. , 2011, Organic Letters.

[16]  L. Toupet,et al.  Stereoselective Synthesis of3-Amino-3-deoxy-aldohexoses by Aldol Condensation of Tricarbonyliron-α-AminodienoneComplexes: Total Synthesis of Multiprotected Kanosamine , 2011 .

[17]  T. Okauchi,et al.  CO insertion in lithiated diene-tricarbonyliron complexes. , 2010, Chemical communications.

[18]  N. Matsunaga,et al.  Halogenated Catechols from Cycloaddition Reactions of η4‐(2‐Ethoxyvinylketene)iron(0) Complexes with 1‐Haloalkynes. , 2010 .

[19]  C. Ong,et al.  Diastereoselective synthesis of a highly functionalized angularly substituted cis-perhydroisoquinoline-3,6-dione via organoiron. , 2010, The Journal of organic chemistry.

[20]  N. Matsunaga,et al.  Halogenated catechols from cycloaddition reactions of η-(2-ethoxyvinylketene)iron(0) complexes with 1-haloalkynes. , 2010, Tetrahedron letters.

[21]  W. A. Donaldson,et al.  Recent Applications of Acyclic (Diene)iron Complexes and (Dienyl)iron Cations in Organic Synthesis. , 2009, European journal of organic chemistry.

[22]  Atiq-Ur-Rehman,et al.  Incorporation of hexafluorobutyne into furans or phenols via reaction with iron(0) carbene or vinylketene complexes. , 2009, Tetrahedron letters.

[23]  R. S. Paley Iron: Organometallic ChemistryBased in part on the article Iron: Organometallic Chemistry by James R. Green which appeared in the Encyclopedia of Inorganic Chemistry, First Edition. , 2006 .

[24]  N. Manolache,et al.  The cycloaddition reactions of 2-ethoxy-3-phenylvinylketene iron(0) with alkynes to yield catechol derivatives , 2006 .

[25]  Fengping Xiao,et al.  1,2-vinyl and 1,2-acetylenyl migration in Rh(II) carbene reaction: remarkable bystander effect. , 2005, The Journal of organic chemistry.

[26]  Jianbo Wang,et al.  Unusual Reaction of β-Hydroxy α-Diazo Carbonyl Compounds with Cl3CCN/NaH and Rh(II)-Catalyzed Reaction of β-Trichloroacetylamino α-Diazo Carbonyl Compounds. , 2003 .

[27]  D. Dvořák,et al.  Thermolysis of Iron N-Allylaminocarbene Complexes: Formation of η3-1-Azaallylirontricarbonyl Complexes. Synthetic and Theoretical Study , 2003 .

[28]  D. Du,et al.  Unusual Reaction of β-Hydroxy α-Diazo Carbonyl Compounds with Cl3CCN/NaH and Rh(II)-Catalyzed Reaction of β-Trichloroacetylamino α-Diazo Carbonyl Compounds , 2003 .

[29]  D. Dvořák,et al.  Iron Aminocarbene Complexes Containing a Double CC Bond in the N-Substituent: Preparation and Reactivity , 2001 .

[30]  T. Okauchi,et al.  Regioselective Proton Abstraction and 1,3-Migration of a Phosphorus Group in 1,3-Dienes by Iron Coordination: A New Method for the Synthesis of α-Phosphono-α,β-unsaturated Ketones , 2001 .

[31]  S. Gibson,et al.  Transition Metal Complexes of Vinylketenes , 1999 .

[32]  S. Gibson,et al.  A Stereochemical study of the reaction between tricarbonyl(vinylketene)iron(O)complexes and alkynes , 1997 .

[33]  A. Slawin,et al.  Synthesis and Oxidation of the Decarbonylated Adducts Generated from Alkenes and Tricarbonyl(vinylketene)iron(0) Complexes. , 1996 .

[34]  S. Gibson,et al.  A stereochemical study of the reaction between tricarbonyl(vinylketene)iron(0) complexes and isonitriles , 1996 .

[35]  H. Masuda,et al.  SYNTHESIS, STRUCTURE, AND REACTIVITIES OF TRIFLUOROMETHYL-SUBSTITUTED (PI -VINYLCARBENE)IRON COMPLEXES , 1995 .

[36]  S. Gibson,et al.  Phosphoramidate mediated conversion of tricarbonyl(vinylketene)iron(0) complexes into tricarbonyl(vinylketenimine)iron(0) complexes , 1995 .

[37]  A. Slawin,et al.  Synthesis and oxidation of the decarbonylated adducts generated from alkenes and tricarbonyl(vinylketene)iron(0) complexes , 1995 .

[38]  A. Slawin,et al.  A study of the reactivity of tricarbonyl(vinylketene)iron(0) complexes towards alkynes , 1993 .

[39]  Susan E. Thomas,et al.  Conversion of adducts formed from tricarbonyl(vinylketene)iron(0) complexes and alkynes into cyclopentenediones and phenols , 1993 .

[40]  C. Richards,et al.  Synthesis and reactivity of iron tricarbonyl complexes of vinyl ketenes, vinyl ketenimines and vinylallenes , 1992 .

[41]  A. Slawin,et al.  Addition of alkynes to (vinylketene)tricarbonyliron(0) complexes , 1992 .

[42]  C. Richards,et al.  Nucleophilic addition to vinylketenimine complexes. The asymmetric synthesis of carbon quaternary centres , 1992 .

[43]  C. Richards,et al.  Preparation of tricarbonyl(.eta.4-vinylketene)iron(0) complexes from tricarbonyl(.eta.4-vinyl ketone)iron(0) complexes and their subsequent conversion to tricarbonyl(.eta.4-vinylketenimine)iron(0) complexes , 1991 .

[44]  C. Richards,et al.  Conversion of (Vinylketene)tricarbonyliron(0) Complexes to (Vinylketenimine)tricarbonyliron(0) Complexes. , 1990 .

[45]  C. Richards,et al.  Nucleophilic addition to vinylketene- and vinylketenimine (allenylideneamine)tricarbonyliron(0) complexes , 1990 .

[46]  Yoshihisa Watanabe,et al.  Reactions of (1-3-.eta.-vinylcarbene)tricarbonyliron complexes with carbon monoxide or tertiary phosphines. "Insertion" of carbon monoxide into a carbon-metal double bond and reactivities of the formed tricarbonyl(.eta.3:.eta.1-allylacyl)irons , 1989 .

[47]  M. Baird,et al.  The preparation and decomposition of alkyl 2-diazopent-4-enoates and 1-trimethylsilyl-1-diazobut-3-enes , 1987 .

[48]  Lilly Capuano,et al.  Reaktionen von Allylidenphosphoranen mit Heterokumulenen, I. Vinylketenimine , 1982 .

[49]  Yoshihisa Watanabe,et al.  Synthesis, crystal structure and reactivities of the first η4-vinylketenimine metal complexes , 1980 .

[50]  M. Schneider,et al.  Formation of Diazo Compounds on Decomposition of 2,3-Diazabicyclo[3.1.0]hex-2-enes:[3+2]-Cycloreversions† , 1977 .