Catalytic Synthesis of Superlinear Alkenyl Arenes Using a Rh(I) Catalyst Supported by a “Capping Arene” Ligand: Access to Aerobic Catalysis

Chen, Junqi; Nielsen, Robert J.; Goddard, William A.; McKeown, Bradley A.; Dickie, Diane A.; Gunnoe, T. Brent

doi:10.1021/jacs.8b07728

Title: Catalytic Synthesis of Superlinear Alkenyl Arenes Using a Rh(I) Catalyst Supported by a “Capping Arene” Ligand: Access to Aerobic Catalysis

Journal Article · 29 November 2018 · Journal of the American Chemical Society

DOI: https://doi.org/10.1021/jacs.8b07728 · OSTI ID:1596588

Chen, Junqi ^[1];

^[2];

^[2]; McKeown, Bradley A. ^[1];

^[1];

^[1]

Univ. of Virginia, Charlottesville, VA (United States)
California Inst. of Technology (CalTech), Pasadena, CA (United States)

Alkyl and alkenyl arenes are used in a wide range of products. Yet, the synthesis of 1-phenylalkanes or their alkenyl variants from arenes and alkenes is not accessible with current commercial acid-based catalytic processes. Here, it is reported that an air-stable Rh(I) complex, (5-FP)Rh(TFA)(η²-C₂H₄) (5-FP = 1,2-bis(N-7-azaindolyl)benzene; TFA = trifluoroacetate), serves as a catalyst precursor for the oxidative conversion of arenes and alkenes to alkenyl arenes that are precursors to 1-phenylalkanes upon hydrogenation. It has been demonstrated that coordination of the 5-FP ligand enhances catalyst longevity compared to unligated Rh(I) catalyst precursors, and the 5-FP-ligated catalyst permits in situ recycling of the Cu(II) oxidant using air. The 5-FP ligand offers a Rh catalyst that can maintain activity for arene alkenylation over at least 2 weeks in reactions at 150 °C that involve multiple Cu(II) regeneration steps using air. Conditions to achieve >13 000 catalytic turnovers with an 8:1 linear:branched (L:B) ratio have been demonstrated. In addition, the catalyst is active under aerobic conditions using air as the sole oxidant. At 80 °C, an 18:1 L:B ratio of alkenyl arenes has been observed, but the reaction rate is substantially reduced compared to 150 °C. Quantum mechanics (QM) calculations compare two predicted reaction pathways with the experimental data, showing that an oxidative addition/reductive elimination pathway is energetically favored over a pathway that involves C–H activation by concerted metalation–deprotonation. In addition, our QM computations are consistent with the observed selectivity (11:1) for linear alkenyl arene products.

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Research Organization:: Univ. of Virginia, Charlottesville, VA (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences, and Biosciences Division; National Science Foundation (NSF)

Grant/Contract Number:: SC0000776; CBET-15127509; ACI-1053575

OSTI ID:: 1596588

Journal Information:: Journal of the American Chemical Society, Vol. 140, Issue 49; ISSN 0002-7863

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 24 works

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References (66)

Production of linear alkylbenzenes Kocal, Joseph A.; Vora, Bipin V.; Imai, Tamotsu Applied Catalysis A: General, Vol. 221, Issue 1-2 https://doi.org/10.1016/S0926-860X(01)00808-0	journal	November 2001
Recent advances in the industrial alkylation of aromatics: new catalysts and new processes Perego, Carlo; Ingallina, Patrizia Catalysis Today, Vol. 73, Issue 1-2 https://doi.org/10.1016/S0920-5861(01)00511-9	journal	April 2002
Ethylbenzene synthesis and benzene transalkylation with diethylbenzenes on zeolite catalysts Gerzeliev, I. M.; Khadzhiev, S. N.; Sakharova, I. E. Petroleum Chemistry, Vol. 51, Issue 1 https://doi.org/10.1134/S0965544111010038	journal	January 2011
Acid-Catalyzed Synthesis of Mono- and Dialkyl Benzenes over Zeolites: Active Sites, Zeolite Topology, and Reaction Mechanisms Čejka, Jiří; Wichterlová, Blanka Catalysis Reviews, Vol. 44, Issue 3 https://doi.org/10.1081/CR-120005741	journal	August 2002
Combining alkylation and transalkylation for alkylaromatic production Perego, Carlo; Ingallina, Patrizia Green Chemistry, Vol. 6, Issue 6 https://doi.org/10.1039/b403277m	journal	January 2004
Linear alkylbenzene de Almeida, J. L. G.; Dufaux, M.; Taarit, Y. Ben Journal of the American Oil Chemists’ Society, Vol. 71, Issue 7 https://doi.org/10.1007/BF02541423	journal	July 1994
Anti-Markovnikov Olefin Arylation Catalyzed by an Iridium Complex Matsumoto, Takaya; Taube, Douglas J.; Periana, Roy A. Journal of the American Chemical Society, Vol. 122, Issue 30 https://doi.org/10.1021/ja0009830	journal	August 2000
Transition metal catalyzed hydroarylation of olefins using unactivated substrates: Recent developments and challenges Andreatta, Jeremy R.; McKeown, Bradley A.; Gunnoe, T. Brent Journal of Organometallic Chemistry, Vol. 696, Issue 1 https://doi.org/10.1016/j.jorganchem.2010.09.030	journal	January 2011
Ru(II) Catalysts Supported by Hydridotris(pyrazolyl)borate for the Hydroarylation of Olefins: Reaction Scope, Mechanistic Studies, and Guides for the Development of Improved Catalysts Foley, Nicholas A.; Lee, John P.; Ke, Zhuofeng Accounts of Chemical Research, Vol. 42, Issue 5 https://doi.org/10.1021/ar800183j	journal	May 2009
Mechanism of Homogeneous Ir(III) Catalyzed Regioselective Arylation of Olefins Oxgaard, Jonas; Muller, Richard P.; Goddard, William A. Journal of the American Chemical Society, Vol. 126, Issue 1 https://doi.org/10.1021/ja034126i	journal	January 2004
Novel bis-acac-O,O–Ir( iii ) catalyst for anti-Markovnikov, hydroarylation of olefins operates by arene CH activation Periana, Roy A.; Liu, Xiang Y.; Bhalla, Gaurav Chem. Commun., Issue 24 https://doi.org/10.1039/B208680H	journal	January 2002
Anti-Markovnikov Hydroarylation of Unactivated Olefins Catalyzed by a Bis-tropolonato Iridium(III) Organometallic Complex Bhalla, Gaurav; Oxgaard, Jonas; Goddard, William A. Organometallics, Vol. 24, Issue 13 https://doi.org/10.1021/om0501733	journal	June 2005
Mechanistic Analysis of Hydroarylation Catalysts Oxgaard, Jonas; Periana, Roy A.; Goddard, William A. Journal of the American Chemical Society, Vol. 126, Issue 37 https://doi.org/10.1021/ja048841j	journal	September 2004
Mechanism of efficient anti-Markovnikov olefin hydroarylation catalyzed by homogeneous Ir( iii ) complexes Bhalla, Gaurav; Bischof, Steven M.; Ganesh, Somesh K. Green Chem., Vol. 13, Issue 1 https://doi.org/10.1039/C0GC00330A	journal	January 2011
Control of Olefin Hydroarylation Catalysis via a Sterically and Electronically Flexible Platinum(II) Catalyst Scaffold McKeown, Bradley A.; Gonzalez, Hector Emanuel; Michaelos, Thoe Organometallics, Vol. 32, Issue 14 https://doi.org/10.1021/om400390e	journal	June 2013
Hydrophenylation of ethylene using a cationic Ru( ii ) catalyst: comparison to a neutral Ru( ii ) catalyst Burgess, Samantha A.; Joslin, Evan E.; Gunnoe, T. Brent Chem. Sci., Vol. 5, Issue 11 https://doi.org/10.1039/C4SC01665C	journal	January 2014
Mechanistic Studies of Ethylene Hydrophenylation Catalyzed by Bipyridyl Pt(II) Complexes McKeown, Bradley A.; Gonzalez, Hector Emanuel; Friedfeld, Max R. Journal of the American Chemical Society, Vol. 133, Issue 47 https://doi.org/10.1021/ja206064v	journal	November 2011
Pt ^II -Catalyzed Ethylene Hydrophenylation: Influence of Dipyridyl Chelate Ring Size on Catalyst Activity and Longevity McKeown, Bradley A.; Gonzalez, Hector Emanuel; Gunnoe, T. Brent ACS Catalysis, Vol. 3, Issue 6 https://doi.org/10.1021/cs400231f	journal	April 2013
Combined Experimental and Computational Study of TpRu{P(pyr) ₃ }(NCMe)Me (pyr = N -pyrrolyl): Inter- and Intramolecular Activation of C−H Bonds and the Impact of Sterics on Catalytic Hydroarylation of Olefins Foley, Nicholas A.; Lail, Marty; Gunnoe, T. Brent Organometallics, Vol. 26, Issue 23 https://doi.org/10.1021/om700666y	journal	November 2007
Aromatic C−H Activation and Catalytic Hydrophenylation of Ethylene by TpRu{P(OCH ₂ ) ₃ CEt}(NCMe)Ph Foley, Nicholas A.; Ke, Zhuofeng; Gunnoe, T. Brent Organometallics, Vol. 27, Issue 13 https://doi.org/10.1021/om800275b	journal	July 2008
Catalytic Hydroarylation of Ethylene Using TpRu(L)(NCMe)Ph (L = 2,6,7-Trioxa-1-phosphabicyclo[2,2,1]heptane): Comparison to TpRu(L′)(NCMe)Ph Systems (L′ = CO, PMe ₃ , P(pyr) ₃ , or P(OCH ₂ ) ₃ CEt) Joslin, Evan E.; McMullin, Claire L.; Gunnoe, T. Brent Organometallics, Vol. 31, Issue 19 https://doi.org/10.1021/om300676e	journal	September 2012
Platinum(II)-Catalyzed Ethylene Hydrophenylation: Switching Selectivity between Alkyl- and Vinylbenzene Production McKeown, Bradley A.; Gonzalez, H. Emanuel; Friedfeld, Max R. Organometallics, Vol. 32, Issue 9 https://doi.org/10.1021/om400306w	journal	April 2013
Addition of Arenes to Ethylene and Propene Catalyzed by Ruthenium Lail, Marty; Arrowood, Benjamin N.; Gunnoe, T. Brent Journal of the American Chemical Society, Vol. 125, Issue 25 https://doi.org/10.1021/ja035076k	journal	June 2003
Experimental and Computational Studies of Ruthenium(II)-Catalyzed Addition of Arene C−H Bonds to Olefins Lail, Marty; Bell, Christen M.; Conner, David Organometallics, Vol. 23, Issue 21 https://doi.org/10.1021/om049404g	journal	October 2004
Intermolecular Hydroarylation of Unactivated Olefins Catalyzed by Homogeneous Platinum Complexes Luedtke, Avery T.; Goldberg, Karen I. Angewandte Chemie International Edition, Vol. 47, Issue 40 https://doi.org/10.1002/anie.200800524	journal	September 2008
Platinum(II) Olefin Hydroarylation Catalysts: Tuning Selectivity for the anti-Markovnikov Product Clement, Marie L.; Grice, Kyle A.; Luedtke, Avery T. Chemistry - A European Journal, Vol. 20, Issue 52 https://doi.org/10.1002/chem.201405174	journal	November 2014
Hydroarylation of Unactivated Olefins Catalyzed by Platinum(II) Complexes McKeown, Bradley A.; Foley, Nicholas A.; Lee, John P. Organometallics, Vol. 27, Issue 16 https://doi.org/10.1021/om8006008	journal	August 2008
Pt ^II -Catalyzed Hydrophenylation of α-Olefins: Variation of Linear/Branched Products as a Function of Ligand Donor Ability McKeown, Bradley A.; Prince, Bruce M.; Ramiro, Zoraida ACS Catalysis, Vol. 4, Issue 5 https://doi.org/10.1021/cs400988w	journal	April 2014
Linear-Selective Hydroarylation of Unactivated Terminal and Internal Olefins with Trifluoromethyl-Substituted Arenes Bair, Joseph S.; Schramm, York; Sergeev, Alexey G. Journal of the American Chemical Society, Vol. 136, Issue 38 https://doi.org/10.1021/ja505579f	journal	September 2014
Catalytic dehydroaromatization of n-alkanes by pincer-ligated iridium complexes Ahuja, Ritu; Punji, Benudhar; Findlater, Michael Nature Chemistry, Vol. 3, Issue 2 https://doi.org/10.1038/nchem.946	journal	December 2010
Catalytic Synthesis of n -Alkyl Arenes through Alkyl Group Cross-Metathesis Dobereiner, Graham E.; Yuan, Jian; Schrock, Richard R. Journal of the American Chemical Society, Vol. 135, Issue 34 https://doi.org/10.1021/ja4066392	journal	August 2013
Regioselective alkylation of 2-phenylpyridines with terminal alkenes via C–H bond activation by a rhodium catalyst Lim, Yeong-Gweon; Kang, Jung-Bu; Kim, Yong Hae J. Chem. Soc., Perkin Trans. 1, Issue 17 https://doi.org/10.1039/P19960002201	journal	January 1996
A rhodium catalyst for single-step styrene production from benzene and ethylene Vaughan, B. A.; Webster-Gardiner, M. S.; Cundari, T. R. Science, Vol. 348, Issue 6233 https://doi.org/10.1126/science.aaa2260	journal	April 2015
Mechanistic Studies of Single-Step Styrene Production Using a Rhodium(I) Catalyst Vaughan, Benjamin A.; Khani, Sarah K.; Gary, J. Brannon Journal of the American Chemical Society, Vol. 139, Issue 4 https://doi.org/10.1021/jacs.6b10658	journal	January 2017
Catalytic Synthesis of “Super” Linear Alkenyl Arenes Using an Easily Prepared Rh(I) Catalyst Webster-Gardiner, Michael S.; Chen, Junqi; Vaughan, Benjamin A. Journal of the American Chemical Society, Vol. 139, Issue 15 https://doi.org/10.1021/jacs.7b01165	journal	April 2017
Acetaldehyde from Ethylene-A Retrospective on the Discovery of the Wacker Process Jira, Reinhard Angewandte Chemie International Edition, Vol. 48, Issue 48 https://doi.org/10.1002/anie.200903992	journal	October 2009
The Oxidation of Olefins with Palladium Chloride Catalysts Smidt, Juergen; Hafner, W.; Jira, R. Angewandte Chemie International Edition in English, Vol. 1, Issue 2 https://doi.org/10.1002/anie.196200801	journal	February 1962
Über die Reaktionen von Olefinen mit wäßrigen Lösungen von Palladiumsalzen Hafner, Walter; Jira, Reinhard; Sedlmeier, Josef Chemische Berichte, Vol. 95, Issue 7 https://doi.org/10.1002/cber.19620950702	journal	July 1962
Katalytische Umsetzungen von Olefinen an Platinmetall-Verbindungen Das Consortium-Verfahren zur Herstellung von Acetaldehyd Smidt, J.; Hafner, W.; Jira, R. Angewandte Chemie, Vol. 71, Issue 5 https://doi.org/10.1002/ange.19590710503	journal	March 1959
Rhodium Complexes Promoting C−O Bond Formation in Reactions with Oxygen: The Role of Superoxo Species Vilella-Arribas, Laia; García-Melchor, Max; Balcells, David Chemistry - A European Journal, Vol. 23, Issue 22 https://doi.org/10.1002/chem.201605959	journal	March 2017
Rhodium-Mediated Formation of Peroxides from Dioxygen: Isolation of Hydroperoxo, Silylperoxo, and Methylperoxo Intermediates Ahijado, Marcel; Braun, Thomas; Noveski, Daniel Angewandte Chemie International Edition, Vol. 44, Issue 42 https://doi.org/10.1002/anie.200501615	journal	October 2005
N -Heterocyclic Carbene Complexes of Rh: Reaction with Dioxygen without Oxidation Praetorius, Jeremy M.; Allen, Daryl P.; Wang, Ruiyao Journal of the American Chemical Society, Vol. 130, Issue 12 https://doi.org/10.1021/ja7108213	journal	March 2008
Rhodium Bis(quinolinyl)benzene Complexes for Methane Activation and Functionalization Fu, Ross; O'Reilly, Matthew E.; Nielsen, Robert J. Chemistry - A European Journal, Vol. 21, Issue 3 https://doi.org/10.1002/chem.201405460	journal	November 2014
Long-Range C–H Bond Activation by Rh ^III -Carboxylates O’Reilly, Matthew E.; Fu, Ross; Nielsen, Robert J. Journal of the American Chemical Society, Vol. 136, Issue 42 https://doi.org/10.1021/ja508367m	journal	October 2014
Transition-Metal-Mediated Nucleophilic Aromatic Substitution with Acids O’Reilly, Matthew E.; Johnson, Samantha I.; Nielsen, Robert J. Organometallics, Vol. 35, Issue 12 https://doi.org/10.1021/acs.organomet.6b00285	journal	June 2016
Regioselective C−H Activation of Toluene with a 1,2-Bis( N- 7-azaindolyl)benzene Platinum(II) Complex Zhao, Shu-Bin; Song, Datong; Jia, Wen-Li Organometallics, Vol. 24, Issue 13 https://doi.org/10.1021/om050133z	journal	June 2005
Olefin Rotation in the Solid State: A 13C, 1H, and 2H NMR Study of Rh(acac)(C2H4)2 Vierkoetter, Stephanie A.; Barnes, Craig E.; Garner, Greta L. Journal of the American Chemical Society, Vol. 116, Issue 16 https://doi.org/10.1021/ja00095a073	journal	August 1994
Rhodium Phosphine−π-Arene Intermediates in the Hydroamination of Alkenes Liu, Zhijian; Yamamichi, Hideaki; Madrahimov, Sherzod T. Journal of the American Chemical Society, Vol. 133, Issue 8 https://doi.org/10.1021/ja1057949	journal	March 2011
Evidence for the ready insertion of rhodium into a carbon–hydrogen bond of ethylene; crystal and molecular structure of µ-but-2-ene-µ-ethylene-bis-(η ⁵ -1-methylindenyl)dirhodium Caddy, Peter; Green, Michael; Smart, Lesley E. J. Chem. Soc., Chem. Commun., Issue 19 https://doi.org/10.1039/C39780000839	journal	January 1978
Crystal structure of (C5H5)Rh(C2F4) (C2H4). Comparison of rhodium-ethylene and rhodium-tetrafluoroethylene bonding Guggenberger, Lloyd J.; Cramer, Richard Journal of the American Chemical Society, Vol. 94, Issue 11 https://doi.org/10.1021/ja00766a019	journal	May 1972
X-ray crystal structure and molecular dynamics of (indenyl)bis(ethylene)rhodium(I): 500-MHz NMR spectra and EHMO calculations Mlekuz, Michael.; Bougeard, Peter.; Sayer, Brian G. Organometallics, Vol. 5, Issue 8 https://doi.org/10.1021/om00139a024	journal	August 1986
Olefin Coordination Compounds of Rhodium: The Barrier to Rotation of Coordinated Ethylene and the Mechanism of Olefin Exchange Cramer, Richard. Journal of the American Chemical Society, Vol. 86, Issue 2 https://doi.org/10.1021/ja01056a022	journal	January 1964
Synthesis, Characterization, and Reactivity of Rhodium(I) Acetylacetonato Complexes Containing Pyridinecarboxaldimine Ligands Kanas, Diane A.; Geier, Stephen J.; Vogels, Christopher M. Inorganic Chemistry, Vol. 47, Issue 19 https://doi.org/10.1021/ic800703n	journal	September 2008
Bulky rhodium diimine complexes for the catalyzed borylation of vinylarenes Geier, Stephen J.; Chapman, Erin E.; McIsaac, Daniel I. Inorganic Chemistry Communications, Vol. 9, Issue 8 https://doi.org/10.1016/j.inoche.2006.05.001	journal	August 2006
Steric Control over Arene Coordination toβ-Diiminate Rhodium(I) Fragments Budzelaar, Peter H. M.; Moonen, Nicolle N. P.; de Gelder, René Chemistry - A European Journal, Vol. 6, Issue 15 https://doi.org/10.1002/1521-3765(20000804)6:15<2740::AID-CHEM2740>3.0.CO;2-0	journal	August 2000
Direct Synthesis of Styrene by Rhodium-Catalyzed Oxidative Arylation of Ethylene with Benzene Matsumoto, Takaya; Periana, Roy A.; Taube, Douglas J. Journal of Catalysis, Vol. 206, Issue 2 https://doi.org/10.1006/jcat.2001.3471	journal	March 2002
Oxidative Arylation of Ethylene with Benzene to Produce Styrene Matsumoto, Takaya; Yoshida, Hajime Chemistry Letters, Vol. 29, Issue 9 https://doi.org/10.1246/cl.2000.1064	journal	September 2000
Ru-Catalyzed Oxidative Coupling of Arenes with Olefins Using O ₂ Weissman, Haim; Song, Xiaoping; Milstein, David Journal of the American Chemical Society, Vol. 123, Issue 2 https://doi.org/10.1021/ja003361n	journal	January 2001
Synthesis and Reactivity of Bis(ethene) Rhodium(I) and Iridium(I) Carboxylato Complexes Werner, Helmut; Poelsma, Sybo; Schneider, Michael E. Chemische Berichte, Vol. 129, Issue 6 https://doi.org/10.1002/cber.19961290609	journal	June 1996
Overview of the Mechanistic Work on the Concerted Metallation–Deprotonation Pathway Lapointe, David; Fagnou, Keith Chemistry Letters, Vol. 39, Issue 11 https://doi.org/10.1246/cl.2010.1118	journal	November 2010
Pd-Mediated Activation of Molecular Oxygen in a Nonpolar Medium Keith, Jason M.; Nielsen, Robert J.; Oxgaard, Jonas Journal of the American Chemical Society, Vol. 127, Issue 38 https://doi.org/10.1021/ja043094b	journal	September 2005
Mechanism of Direct Molecular Oxygen Insertion in a Palladium(II)−Hydride Bond Keith, Jason M.; Muller, Richard P.; Kemp, Richard A. Inorganic Chemistry, Vol. 45, Issue 24 https://doi.org/10.1021/ic061392z	journal	November 2006
Reaction of O ₂ with [(−)-Sparteine]Pd(H)Cl: Evidence for an Intramolecular [H–L] ⁺ “Reductive Elimination” Pathway Decharin, Nattawan; Popp, Brian V.; Stahl, Shannon S. Journal of the American Chemical Society, Vol. 133, Issue 34 https://doi.org/10.1021/ja204989p	journal	August 2011
Dioxygen insertion into the gold( i )–hydride bond: spin orbit coupling effects in the spotlight for oxidative addition Gaggioli, Carlo Alberto; Belpassi, Leonardo; Tarantelli, Francesco Chemical Science, Vol. 7, Issue 12 https://doi.org/10.1039/C6SC02161A	journal	January 2016
Pd-Mediated Activation of Molecular Oxygen: Pd(0) versus Direct Insertion Keith, Jason M.; Goddard, William A.; Oxgaard, Jonas Journal of the American Chemical Society, Vol. 129, Issue 34 https://doi.org/10.1021/ja070462d	journal	August 2007
Autoxidation of Platinum(IV) Hydrocarbyl Hydride Complexes To Form Platinum(IV) Hydrocarbyl Hydroperoxide Complexes Look, Jennifer L.; Wick, Douglas D.; Mayer, James M. Inorganic Chemistry, Vol. 48, Issue 4 https://doi.org/10.1021/ic801216r	journal	February 2009

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Title: Catalytic Synthesis of Superlinear Alkenyl Arenes Using a Rh(I) Catalyst Supported by a “Capping Arene” Ligand: Access to Aerobic Catalysis

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