Fe-Promoted C–F Activation of Aryl Fluorides Enables Heck-Type Coupling with Alkenes and One-Pot Synthesis of Indenes

Radzhabov, Maxim R.; Mankad, Neal P.

doi:10.1021/acs.organomet.3c00256

Fe-Promoted C–F Activation of Aryl Fluorides Enables Heck-Type Coupling with Alkenes and One-Pot Synthesis of Indenes

Journal Article · Thu Jul 27 00:00:00 EDT 2023 · Organometallics

DOI:https://doi.org/10.1021/acs.organomet.3c00256· OSTI ID:2421708

Radzhabov, Maxim R. ^[1]; ^[2]

Department of Chemistry, University of Illinois at Chicago 845 W. Taylor St., Chicago, Illinois 60607, United States; OSTI
Department of Chemistry, University of Illinois at Chicago 845 W. Taylor St., Chicago, Illinois 60607, United States

Not provided.

Research Organization:: Univ. of Illinois at Urbana-Champaign, IL (United States)

Sponsoring Organization:: USDOE Office of Science (SC)

DOE Contract Number:: SC0021055

OSTI ID:: 2421708

Journal Information:: Organometallics, Journal Name: Organometallics Journal Issue: 15 Vol. 42; ISSN 0276-7333

Publisher:: American Chemical Society

Country of Publication:: United States

Language:: English

References (71)

New triple-decker complexes prepared by the stacking reactions of cationic metallofragments with sandwich compounds Kudinov, A. R.; Rybinskaya, M. I. Russian Chemical Bulletin, Vol. 48, Issue 9 https://doi.org/10.1007/BF02494802	journal	September 1999
Organometallic chemistry using partially fluorinated benzenes Pike, Sebastian D.; Crimmin, Mark R.; Chaplin, Adrian B. Chemical Communications, Vol. 53, Issue 26 https://doi.org/10.1039/C6CC09575E	journal	January 2017
Organometallic Electrochemistry. VII.¹ The Nucleophilicities of Metallic and Metalloidal Anions Derived from Metals of Groups IV, V, VI, VII, and VIII Dessy, Raymond E.; Pohl, Rudolph L.; King, R. Bruce Journal of the American Chemical Society, Vol. 88, Issue 22 https://doi.org/10.1021/ja00974a015	journal	November 1966
Synthesis of indenols and indanones via catalytic cyclic vinylpalladation of aromatic aldehydes Gevorgyan, Vladimir; Quan, Long Guo; Yamamoto, Yoshinori Tetrahedron Letters, Vol. 40, Issue 21 https://doi.org/10.1016/S0040-4039(99)00656-5	journal	May 1999
Routes to fluorinated organic derivatives by nickel mediated C–F activation of heteroaromatics Braun, Thomas; Perutz, Robin N. Chem. Commun., Issue 23 https://doi.org/10.1039/B206154F	journal	January 2002
Carbon−Fluorine Bond Cleavage by Zirconium Metal Hydride Complexes Edelbach, Brian L.; Fazlur Rahman, A. K.; Lachicotte, Rene J. Organometallics, Vol. 18, Issue 16 https://doi.org/10.1021/om9902481	journal	July 1999
Fluorine in medicinal chemistry Purser, Sophie; Moore, Peter R.; Swallow, Steve Chem. Soc. Rev., Vol. 37, Issue 2 https://doi.org/10.1039/B610213C	journal	January 2008
The chemistry of (.eta.5-cyclopentadienyl)dicarbonyliron hydride revisited Shackleton, Thomas A.; Mackie, Stephen C.; Fergusson, Stuart B. Organometallics, Vol. 9, Issue 8 https://doi.org/10.1021/om00158a023	journal	August 1990
Synthesis of μ-Diborolyl Triple-Decker Complexes by Electrophilic Stacking. Similar Bonding Properties of Anions [CpCo(1,3-C₃B₂H₅)]⁻ and Cp⁻ toward Transition Metals Siebert, Walter; Kudinov, Alexander R.; Zanello, Piero Organometallics, Vol. 28, Issue 9 https://doi.org/10.1021/om900032z	journal	April 2009
Nucleophilic Reactions of Metal Carbonyl Anions with Fluorocarbons Bruce, M. I.; Stone, F. G. A. Angewandte Chemie International Edition in English, Vol. 7, Issue 10 https://doi.org/10.1002/anie.196807471	journal	October 1968
Triple-decker sandwiches Lauher, Joseph W.; Elian, Mihai; Summerville, Richard H. Journal of the American Chemical Society, Vol. 98, Issue 11 https://doi.org/10.1021/ja00427a028	journal	May 1976
The Coordination Chemistry of the CF Unit in Fluorocarbons Plenio, Herbert Chemical Reviews, Vol. 97, Issue 8 https://doi.org/10.1021/cr970465g	journal	December 1997
Catalytic Hydrodefluorination with Late Transition Metal Complexes Whittlesey, Michael K.; Peris, Eduardo ACS Catalysis, Vol. 4, Issue 9 https://doi.org/10.1021/cs500887p	journal	August 2014
Atmospheric Lifetimes of Long-Lived Halogenated Species Ravishankara, A. R.; Solomon, S.; Turnipseed, A. A. Science, Vol. 259, Issue 5092 https://doi.org/10.1126/science.259.5092.194	journal	January 1993
Free radical participation in the reaction of metalate anions with alkyl halides Krusic, Paul J.; Fagan, Paul J.; San Filippo, Joseph Journal of the American Chemical Society, Vol. 99, Issue 1 https://doi.org/10.1021/ja00443a048	journal	January 1977
C−F Bond Activation in Organic Synthesis Amii, Hideki; Uneyama, Kenji Chemical Reviews, Vol. 109, Issue 5 https://doi.org/10.1021/cr800388c	journal	May 2009
Concise syntheses of (±)-dichroanone, (±)-dichroanal B, (±)-taiwaniaquinol B, and (±)-taiwaniaquinone D Majetich, George; Shimkus, Joel M. Tetrahedron Letters, Vol. 50, Issue 26 https://doi.org/10.1016/j.tetlet.2009.02.074	journal	July 2009
Activation of C–F bonds α to C–C multiple bonds Hamel, Jean-Denys; Paquin, Jean-François Chemical Communications, Vol. 54, Issue 73 https://doi.org/10.1039/C8CC05108A	journal	January 2018
Conjugated Vinylgold(I)‐Vinylideneruthenium(II) Complexes and Related Organoruthenium Compounds: Stable Analogues of Intermediates Proposed in Dual Gold Catalysis Wieteck, Marcel; Larsen née Vilhelmsen, Mie Højer; Nösel, Pascal Advanced Synthesis & Catalysis, Vol. 358, Issue 9 https://doi.org/10.1002/adsc.201600255	journal	April 2016
N-Heterocyclic carbenes in organofluorine chemistry Reddy, V. Prakash; Vadapalli, Avinash; Sinn, Ekkehard Journal of Organometallic Chemistry, Vol. 747 https://doi.org/10.1016/j.jorganchem.2013.04.051	journal	December 2013
Unravelling nucleophilic aromatic substitution pathways with bimetallic nucleophiles Garçon, Martí; Bakewell, Clare; White, Andrew J. P. Chemical Communications, Vol. 55, Issue 12 https://doi.org/10.1039/C8CC09701A	journal	January 2019
Ring-closing metathesis for the synthesis of substituted indenols, indenones, indanones and indenes: Tandem RCM-dehydrogenative oxidation and RCM-formal redox isomerization Coyanis, E. Mabel; Panayides, Jenny-Lee; Fernandes, Manuel A. Journal of Organometallic Chemistry, Vol. 691, Issue 24-25 https://doi.org/10.1016/j.jorganchem.2006.08.074	journal	December 2006
The Unique Role of Fluorine in the Design of Active Ingredients for Modern Crop Protection Jeschke, Peter ChemBioChem, Vol. 5, Issue 5 https://doi.org/10.1002/cbic.200300833	journal	April 2004
Cyclooxygenase-1-Selective Inhibitors Based on the ( E )-2′- Des -methyl-sulindac Sulfide Scaffold Liedtke, Andy J.; Crews, Brenda C.; Daniel, Cristina M. Journal of Medicinal Chemistry, Vol. 55, Issue 5 https://doi.org/10.1021/jm201528b	journal	February 2012
Platinum(II)-Catalyzed Cross-Coupling of Polyfluoroaryl Imines Wang, Tongen; Alfonso, Brian J.; Love, Jennifer A. Organic Letters, Vol. 9, Issue 26 https://doi.org/10.1021/ol702591b	journal	November 2007
Main-Group Lewis Acids for C–F Bond Activation Stahl, Timo; Klare, Hendrik F. T.; Oestreich, Martin ACS Catalysis, Vol. 3, Issue 7 https://doi.org/10.1021/cs4003244	journal	June 2013
Reactions of alkali metal derivatives of metal carbonyls King, R. B.; Bisnette, M. B. Journal of Organometallic Chemistry, Vol. 2, Issue 1 https://doi.org/10.1016/S0022-328X(00)87597-X	journal	June 1964
Indium(III) Trifluoromethanesulfonate: An Efficient Reusable Catalyst for the Alkynylation-Cyclization of 2-Aminoaryl Ketones and Synthesis of 2,4-Disubstituted Quinolines Prajapati, Dipak; Lekhok, Kushal; Boruah, Ramesh Synlett, Vol. 2008, Issue 05 https://doi.org/10.1055/s-2008-1042800	journal	February 2008
Reactions of metal carbonyl derivatives Haines, R. J.; Du Preez, A. L. Journal of Organometallic Chemistry, Vol. 84, Issue 3 https://doi.org/10.1016/S0022-328X(00)91401-3	journal	January 1975
Thermal C–H borylation using a CO-free iron boryl complex Mazzacano, Thomas J.; Mankad, Neal P. Chemical Communications, Vol. 51, Issue 25 https://doi.org/10.1039/C4CC09180A	journal	January 2015
Recent advances in the Heck–Matsuda reaction in heterocyclic chemistry Felpin, François-Xavier; Nassar-Hardy, Luma; Le Callonnec, François Tetrahedron, Vol. 67, Issue 16 https://doi.org/10.1016/j.tet.2011.02.051	journal	April 2011
Nickel-Catalyzed Suzuki–Miyaura Reaction of Aryl Fluorides Tobisu, Mamoru; Xu, Tian; Shimasaki, Toshiaki Journal of the American Chemical Society, Vol. 133, Issue 48 https://doi.org/10.1021/ja207759e	journal	November 2011
C−F Bond Activation and Functionalizations Enabled by Metal‐free NHCs and Their Metal Complexes Muthuvel, Karthick; Gandhi, Thirumanavelan ChemCatChem, Vol. 14, Issue 8 https://doi.org/10.1002/cctc.202101579	journal	February 2022
A New Route to Triple‐Decker Sandwich Compounds Salzer, Albrecht; Werner, Helmut Angewandte Chemie International Edition in English, Vol. 11, Issue 10 https://doi.org/10.1002/anie.197209301	journal	October 1972
Reaction of threo-dicarbonyl-.pi.-cyclopentadienyl(3,3-dimethylbutyl-1,2-d2)iron with triphenylphosphine Whitesides, George M.; Boschetto, David J. Journal of the American Chemical Society, Vol. 91, Issue 15 https://doi.org/10.1021/ja01043a064	journal	July 1969
Cross coupling reactions of polyfluoroarenes via C–F activation Sun, Alex D.; Love, Jennifer A. Dalton Transactions, Vol. 39, Issue 43 https://doi.org/10.1039/C0DT00540A	journal	January 2010
The reaction of acetylenes with compounds containing Fe–Aryl bonds. A convenient and novel synthesis of indenones Butler, Ian R.; Cullen, William R.; Lindsell, W. Edward J. Chem. Soc., Chem. Commun., Issue 6 https://doi.org/10.1039/C39870000439	journal	January 1987
Thermal and photochemical reactions of η⁵-cyclopentadienyl(naphthoyl)(dicarbonyl)iron complexes with alkynes: formation of benzindenones and dihydropentalenones Butler, Ian R.; Charland, Jean-Pierre; Elliot, Joanne L. J. Chem. Soc., Perkin Trans. 1, Issue 10 https://doi.org/10.1039/P19900002799	journal	January 1990
Thermodynamics of the Metal–Hydrogen Bonds in (η ⁵ -C ₅ H ₅ )M(CO) ₂ H (M = Fe, Ru, Os) Estes, Deven P.; Vannucci, Aaron K.; Hall, Ariel R. Organometallics, Vol. 30, Issue 12 https://doi.org/10.1021/om2001519	journal	June 2011
Effects of the nature of halides on the alkyl group isomerization in the nickel-catalyzed cross-coupling of secondary alkyl Grignard reagents with organic halides Kiso, Yoshihisa; Tamao, Kohei; Kumada, Makoto Journal of Organometallic Chemistry, Vol. 50, Issue 1 https://doi.org/10.1016/S0022-328X(00)95063-0	journal	March 1973
Chemical Redox Agents for Organometallic Chemistry Connelly, Neil G.; Geiger, William E. Chemical Reviews, Vol. 96, Issue 2 https://doi.org/10.1021/cr940053x	journal	January 1996
Synthesis and Structures of Triple-Decker Complexes with a Bridging Tetramethylcyclopentadienyl Ligand Ghag, Sonam K.; Tarlton, Michael L.; Henle, Ernst A. Organometallics, Vol. 32, Issue 6 https://doi.org/10.1021/om301258s	journal	February 2013
Arylation of Styrenes with Aryliron Complexes [CpFe(CO)₂Ar] Yasuda, Shigeo; Yorimitsu, Hideki; Oshima, Koichiro Organometallics, Vol. 29, Issue 11 https://doi.org/10.1021/om1001952	journal	May 2010
Visible Light Mediated Heck Coupling of Inactivated Aryl Fluoride/Chloride Over a Sulfonic Acid Functionalized, Melamine‐based Metal‐free Porphyrin Photocatalyst Bhuse, Darpan Vijaykumar; Bhagat, Pundlik Rambhau ChemistrySelect, Vol. 7, Issue 29 https://doi.org/10.1002/slct.202200328	journal	August 2022
Beyond a solvent: triple roles of dimethylformamide in organic chemistry Heravi, Majid M.; Ghavidel, Mahdieh; Mohammadkhani, Leyla RSC Advances, Vol. 8, Issue 49 https://doi.org/10.1039/C8RA04985H	journal	January 2018
Acylation, methylation, and carboxyalkylation of olefins by Group VIII metal derivatives Heck, Richard F. Journal of the American Chemical Society, Vol. 90, Issue 20 https://doi.org/10.1021/ja01022a034	journal	September 1968
Trikentramine, an unusual pyrrole derivative from the sponge trikentrion loeve carter Aknin, Maurice; Miralles, Joseph; Kornprobst, Jean-Michel Tetrahedron Letters, Vol. 31, Issue 21 https://doi.org/10.1016/S0040-4039(00)89003-6	journal	January 1990
The synthesis of bimetallic manganese tricarbonyl-capped metallocenes Watson, Eric J.; Virkaitis, Kurtis L.; Li, Huazhi Chemical Communications, Issue 5 https://doi.org/10.1039/B009054I	journal	January 2001
Metal carbonyl anions as model metal-centered nucleophiles in aromatic and vinylic substitution reactions Sazonov, Petr K.; Ivushkin, Vasyli A.; Artamkina, Galina A. Arkivoc, Vol. 2003, Issue 10 https://doi.org/10.3998/ark.5550190.0004.a30	journal	October 2003
Heterobimetallic Control of Regioselectivity in Alkyne Hydrostannylation: Divergent Syntheses of α- and ( E ) - β - Vinylstannanes via Cooperative Sn–H Bond Activation Cheng, Li-Jie; Mankad, Neal P. Journal of the American Chemical Society, Vol. 141, Issue 8 https://doi.org/10.1021/jacs.9b00068	journal	January 2019
Activation of Carbon-Fluorine Bonds by Metal Complexes Kiplinger, Jaqueline L.; Richmond, Thomas G.; Osterberg, Carolyn E. Chemical Reviews, Vol. 94, Issue 2 https://doi.org/10.1021/cr00026a005	journal	March 1994
Advances in silylation and borylation of fluoroarenes and gem-difluoroalkenes via C–F bond cleavage Zhang, Juan; Geng, Shasha; Feng, Zhang Chemical Communications, Vol. 57, Issue 90 https://doi.org/10.1039/D1CC04729A	journal	January 2021
Recent Advances in Transition‐metal‐catalyzed C−C Bond Formation via C(sp²)−F Bond Cleavage Fu, Liyan; Chen, Qiang; Nishihara, Yasushi The Chemical Record, Vol. 21, Issue 12 https://doi.org/10.1002/tcr.202100053	journal	April 2021
Internally competitive methyl vs. methyl-d3 migration and kinetic isotope effects. Means of determining whether or not methyl migration occurs in the rate-controlling step Schubert, W. M.; LeFevre, Paul H. Journal of the American Chemical Society, Vol. 94, Issue 5 https://doi.org/10.1021/ja00760a035	journal	March 1972
Recent Advances in the Synthesis of Indenes Rinaldi, Antonia; Scarpi, Dina; Occhiato, Ernesto G. European Journal of Organic Chemistry, Vol. 2019, Issue 45 https://doi.org/10.1002/ejoc.201901425	journal	November 2019
Synthesis of Indene Derivatives via Electrophilic Cyclization Khan, Zulfiqar Ali; Wirth, Thomas Organic Letters, Vol. 11, Issue 1 https://doi.org/10.1021/ol8024956	journal	December 2008
Palladium(0)-Catalyzed Amination, Stille Coupling, and Suzuki Coupling of Electron-Deficient Aryl Fluorides Kim, Young Mi; Yu, Shu Journal of the American Chemical Society, Vol. 125, Issue 7 https://doi.org/10.1021/ja028966t	journal	January 2003
C−F Activation of Fluorinated Arenes using NHC-Stabilized Nickel(0) Complexes: Selectivity and Mechanistic Investigations Schaub, Thomas; Fischer, Peter; Steffen, Andreas Journal of the American Chemical Society, Vol. 130, Issue 29 https://doi.org/10.1021/ja074640e	journal	June 2008
Mechanism of arylation and carbomethoxylation of olefins with organopalladium compounds Heck, Richard F. Journal of the American Chemical Society, Vol. 91, Issue 24 https://doi.org/10.1021/ja01052a029	journal	November 1969
π–π Interaction Assisted Hydrodefluorination of Perfluoroarenes by Gold Hydride: A Case of Synergistic Effect on C–F Bond Activation Lv, Hongbin; Zhan, Jin-Hui; Cai, Yuan-Bo Journal of the American Chemical Society, Vol. 134, Issue 39 https://doi.org/10.1021/ja305204y	journal	September 2012
Contribution of Organofluorine Compounds to Pharmaceuticals Inoue, Munenori; Sumii, Yuji; Shibata, Norio ACS Omega, Vol. 5, Issue 19 https://doi.org/10.1021/acsomega.0c00830	journal	April 2020
Nickel-Catalyzed Cross-Coupling Reaction of Aryl Fluorides and Chlorides with Grignard Reagents under Nickel/Magnesium Bimetallic Cooperation Yoshikai, Naohiko; Mashima, Hiroko; Nakamura, Eiichi Journal of the American Chemical Society, Vol. 127, Issue 51 https://doi.org/10.1021/ja056327n	journal	December 2005
Applications of metal carbonyl anions in the synthesis of ususual organometallic compounds King, Robert Bruce Accounts of Chemical Research, Vol. 3, Issue 12 https://doi.org/10.1021/ar50036a004	journal	December 1970
Hydrogen radical-shuttle (HRS)-enabled photoredox synthesis of indanones via decarboxylative annulation Yang, Bo; Li, Shi-Jun; Wang, Yongdong Nature Communications, Vol. 12, Issue 1 https://doi.org/10.1038/s41467-021-25594-4	journal	September 2021
Understanding organofluorine chemistry. An introduction to the C–F bond O'Hagan, David Chem. Soc. Rev., Vol. 37, Issue 2 https://doi.org/10.1039/B711844A	journal	January 2008
Functionalization of Fluorinated Molecules by Transition-Metal-Mediated C–F Bond Activation To Access Fluorinated Building Blocks Ahrens, Theresia; Kohlmann, Johannes; Ahrens, Mike Chemical Reviews, Vol. 115, Issue 2 https://doi.org/10.1021/cr500257c	journal	August 2014
Photochemical Heck benzylation of styrenes catalyzed by Na[FeCp(CO)2] Waldhart, Greyson W.; Mankad, Neal P. Journal of Organometallic Chemistry, Vol. 793 https://doi.org/10.1016/j.jorganchem.2014.12.033	journal	September 2015
Fluorine: A Very Special Element and Its Very Special Impacts on Chemistry Dehnen, Stefanie; Schafer, Laurel L.; Lectka, Thomas Inorganic Chemistry, Vol. 60, Issue 23 https://doi.org/10.1021/acs.inorgchem.1c03509	journal	November 2021
Bond Dissociation Energies of Organic Molecules Blanksby, Stephen J.; Ellison, G. Barney Accounts of Chemical Research, Vol. 36, Issue 4 https://doi.org/10.1021/ar020230d	journal	April 2003
The Heck Reaction as a Sharpening Stone of Palladium Catalysis Beletskaya, Irina P.; Cheprakov, Andrei V. Chemical Reviews, Vol. 100, Issue 8 https://doi.org/10.1021/cr9903048	journal	August 2000
Organometallic Fluorides: Compounds Containing Carbon−Metal−Fluorine Fragments of d-Block Metals ^† Murphy, Eamonn F.; Murugavel, Ramaswamy; Roesky, Herbert W. Chemical Reviews, Vol. 97, Issue 8 https://doi.org/10.1021/cr960365v	journal	December 1997

Similar Records

One‐Pot Synthesis of Xanthone by Carbonylative Suzuki Coupling Reaction

Journal Article · Wed May 12 00:00:00 EDT 2021 · Chemistry Select · OSTI ID:1787401

Photochemical Synthesis of Acyl Fluorides Using Copper-Catalyzed Fluorocarbonylation of Alkyl Iodides

Journal Article · Thu Mar 28 00:00:00 EDT 2024 · Organic Letters · OSTI ID:2577640

“Self-heating” enabled one-pot synthesis of fluorescent carbon dots

Journal Article · Fri Jul 12 00:00:00 EDT 2019 · Engineered Science · OSTI ID:1776509

Related Subjects

Chemistry

Fe-Promoted C–F Activation of Aryl Fluorides Enables Heck-Type Coupling with Alkenes and One-Pot Synthesis of Indenes

Citation Formats

References (71)

Similar Records

Related Subjects