Arene Ruthenium Catalyst MCAT-53 for the Synthesis of Heterobiaryl Compounds in Water through Aromatic C–H Bond Activation

A new water friendly MCAT-53 [Ru2Cl2 (HCOO)3(p-cymene)] Na (sodium η-6-p-cymene dichloro diruthenium triformato complex) has been developed as a catalyst to effect aromatic C–H bond activation and C–C coupling reactions in water. Cross-coupling reactions were performed in DI/distilled water under ai...

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Published inOrganic process research & development Vol. 22; no. 9; pp. 1119 - 1130
Main Authors Mehta, Anita, Saha, Biswajit, Koohang, Ali Aiden, Chorghade, Mukund S
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 21.09.2018
Amer Chemical Soc
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Abstract A new water friendly MCAT-53 [Ru2Cl2 (HCOO)3(p-cymene)] Na (sodium η-6-p-cymene dichloro diruthenium triformato complex) has been developed as a catalyst to effect aromatic C–H bond activation and C–C coupling reactions in water. Cross-coupling reactions were performed in DI/distilled water under air- and ligand-free conditions without further activation of the catalyst. Synthesis of an advanced intermediate of CETP inhibitor, Anacetrapib, in water has been demonstrated to give a single regioisomer using the MCAT-53 catalyst.
AbstractList A new water friendly MCAT-53 [Ru2Cl2 (HCOO)(3)(p-cymene)] Na (sodium eta-6-p-cymene dichloro diruthenium triformato complex) has been developed as a catalyst to effect aromatic C-H bond activation and C-C coupling reactions in water. Cross-coupling reactions were performed in DI/distilled water under air- and ligand-free conditions without further activation of the catalyst. Synthesis of an advanced intermediate of CETP inhibitor, Anacetrapib, in water has been demonstrated to give a single regioisomer using the MCAT-53 catalyst.
A new water friendly MCAT-53 [Ru2Cl2 (HCOO)3(p-cymene)] Na (sodium η-6-p-cymene dichloro diruthenium triformato complex) has been developed as a catalyst to effect aromatic C–H bond activation and C–C coupling reactions in water. Cross-coupling reactions were performed in DI/distilled water under air- and ligand-free conditions without further activation of the catalyst. Synthesis of an advanced intermediate of CETP inhibitor, Anacetrapib, in water has been demonstrated to give a single regioisomer using the MCAT-53 catalyst.
Author Mehta, Anita
Chorghade, Mukund S
Koohang, Ali Aiden
Saha, Biswajit
AuthorAffiliation Chicago Discovery Solutions LLC
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  givenname: Mukund S
  surname: Chorghade
  fullname: Chorghade, Mukund S
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Cites_doi 10.1039/b805701j
10.1021/ol051216e
10.1021/acs.joc.5b02818
10.1055/s-2006-956468
10.1055/s-2007-990838
10.1002/anie.200905967
10.1007/s10563-010-9104-6
10.1016/j.tet.2012.03.117
10.1021/cr000664r
10.1021/cr020033s
10.1039/c2gc36222h
10.1021/ja201462n
10.1021/ol300671y
10.1002/cctc.201700494
10.1002/anie.200806273
10.1016/j.tet.2013.01.006
10.1021/ol900235s
10.1021/ol102187e
10.1021/acscatal.7b01645
10.1002/ejoc.201100238
10.1016/j.tet.2008.01.050
10.1021/ja8091449
10.1021/jo1018574
10.1021/acscatal.7b03648
10.1021/cr900184e
10.1021/ol802252m
10.1055/s-0029-1220010
10.1021/jo050031i
10.1039/b913115a
10.1021/ar3002798
10.1002/anie.200701727
10.1021/ja058451c
10.1039/c2cy20320k
10.1002/anie.200462883
10.1021/ol016257z
10.1021/ja401466y
10.1039/b719493e
10.1021/cr900005n
10.1021/cr300153J
10.1039/c6cs00075d
10.1021/ol9020354
10.1021/ar200190g
10.1002/anie.201703743
10.1002/anie.201002870
10.1021/acs.jmedchem.5b01409
10.1016/j.tetlet.2005.02.096
10.1021/op500330g
10.1002/ajoc.201800241
10.1039/c3gc41042k
10.3390/molecules23030647
10.1021/ol800773x
10.1039/C2GC36222H
10.1021/ja800818b
10.1039/C6CS00075D
10.1021/cen-v086n029.p032
10.1021/cr60307a002
10.1021/cr300153j
10.1007/b10989
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Issue 9
Keywords C−H activation
C−C coupling
ruthenium catalyst
MCAT-53
C-C coupling
FUNCTIONALIZATION
CROSS-COUPLING REACTIONS
CARBOXYLATE
C-H activation
PHENOLS
REACTIVITY
OLEFIN METATHESIS
ARYL
DIRECT ARYLATIONS
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References Ackermann, L (WOS:000256937700016) 2008; 64
Brow, DG (WOS:000376840600003) 2016; 59
Kuzman, P (WOS:000409878300016) 2017; 9
Hofmann, N (WOS:000317872800053) 2013; 135
Nareddy, P (WOS:000410005700019) 2017; 7
Mukherjee, K (WOS:000438338100032) 2018; 7
Oi, S (WOS:000170392300041) 2001; 3
Ackermann, L (WOS:000271097100040) 2009; 11
Skowerski, K (WOS:000310950000003) 2012; 2
(000445711200009.3) 2014
Ackermann, L (WOS:000230213100081) 2005; 7
Ackermann, L (WOS:000251507000013) 2007
Colby, DA (WOS:000274705900003) 2010; 110
Chu, JCK (WOS:000418798600006) 2018; 57
Nishikata, T (WOS:000266546300039) 2009; 11
Kaloglu, N (WOS:000428514100138) 2018; 23
Reisch, MS (WOS:000253881800035) 2008; 86
(000445711200009.1) 2007
Crow, JM (WOS:000254018300049) 2008; 5
Diers, E (WOS:000318457900013) 2013; 69
Ackermann, L (WOS:000302990100050) 2012; 14
Narayan, S (WOS:000229516300022) 2005; 44
Daugulis, O (WOS:000243569000002) 2006
Ackermann, L (WOS:000249114700031) 2007; 46
Arockiam, PB (WOS:000282477500032) 2010; 49
Ackermann, L (WOS:000283531000083) 2010; 12
Norinder, J (WOS:000255629400014) 2008; 130
Oi, S (WOS:000228367100026) 2005; 70
Arockiam, PB (WOS:000312545400004) 2013; 15
Ackermann, L (WOS:000256281600053) 2008; 10
Korvorapun, K (WOS:000424735000018) 2018; 8
(000445711200009.4) 2007
Denmark, SE (WOS:000264792300069) 2009; 131
McGlacken, GP (WOS:000268184600021) 2009; 38
Hong, SH (WOS:000236299700019) 2006; 128
Hassan, J (WOS:000175550000003) 2002; 102
Nishikata, T (WOS:000274424000022) 2010; 49
Gensch, T (WOS:000376520800009) 2016; 45
Ackermann, L (WOS:000348332000024) 2015; 19
Arockiam, P (WOS:000271476500026) 2009; 11
Arockiam, PB (WOS:000311239600009) 2012; 112
Flegeau, EF (WOS:000292715600044) 2011; 133
TOLMAN, CA (WOS:A1977DG76500002) 1977; 77
Lyons, TW (WOS:000274705900016) 2010; 110
Wada, K (WOS:000287503600001) 2011; 15
Davies, HML (WOS:000369212900001) 2016; 81
Bruneau, C (CCC:000223893900005) 2004; 11
Chen, X (WOS:000267809800005) 2009; 48
Ackermann, L (WOS:000331775200001) 2014; 47
Lipshutz, BH (WOS:000260725100001) 2008; 41
Ackermann, L (WOS:000280299200019) 2010
Horton, DA (WOS:000181603000008) 2003; 103
Gallivan, JP (WOS:000228115600011) 2005; 46
Colby, DA (WOS:000305321100005) 2012; 45
Ouellet, SG (WOS:000287636200024) 2011; 76
Ackermann, L (WOS:000260534500084) 2008; 10
Tomasek, J (WOS:000323179000001) 2013; 15
Murahashi, S.-I. (000445711200009.48) 2005
Stefane, B (WOS:000293133100012) 2011; 2011
Gulajski, L (WOS:000253751400003) 2008; 10
(000445711200009.2) 2016
Li, B (WOS:000305381700010) 2012; 68
ref1/cit1i
ref2/cit2o
ref9/cit9
ref1/cit1h
ref2/cit2n
Lipshutz B. H. (ref3/cit3f) 2008; 4
ref2/cit2m
ref2/cit2l
ref1/cit1e
ref2/cit2s
ref4/cit4f2
ref1/cit1d
ref2/cit2r
ref1/cit1g
ref2/cit2q
ref1/cit1f
ref2/cit2p
ref2/cit2f
ref2/cit2e
ref2/cit2d
ref2/cit2k
ref2/cit2j
ref2/cit2i
ref2/cit2h
ref2/cit2c
ref2/cit2b
ref2/cit2a
ref1/cit1a
ref1/cit1c
ref1/cit1b
ref3/cit3c
ref3/cit3a
ref3/cit3g
ref3/cit3d
ref3/cit3e
ref3/cit3j
ref3/cit3k
ref3/cit3h
ref3/cit3i
Mukherjee K. (ref2/cit2u) 2018; 7
ref11/cit11
ref8/cit8a
ref10/cit10a
ref10/cit10b
ref8/cit8b
ref10/cit10c
ref5/cit5
Murahashi S.-I. (ref2/cit2g) 2005
ref4/cit4a
ref4/cit4b
ref4/cit4c
ref12/cit12
ref4/cit4l
ref4/cit4d
ref4/cit4e
ref4/cit4f
ref2/cit2t
ref4/cit4g
Crow J. M. (ref3/cit3b) 2008
ref4/cit4h
ref4/cit4i
ref4/cit4j
ref4/cit4k
ref7/cit7
References_xml – volume: 38
  start-page: 2447
  year: 2009
  ident: WOS:000268184600021
  article-title: Recent advances in aryl-aryl bond formation by direct arylation
  publication-title: CHEMICAL SOCIETY REVIEWS
  doi: 10.1039/b805701j
  contributor:
    fullname: McGlacken, GP
– volume: 7
  start-page: 3123
  year: 2005
  ident: WOS:000230213100081
  article-title: Phosphine oxides as preligands in ruthenium-catalyzed arylations via C-H bond functionalization using aryl chlorides
  publication-title: ORGANIC LETTERS
  doi: 10.1021/ol051216e
  contributor:
    fullname: Ackermann, L
– volume: 81
  start-page: 343
  year: 2016
  ident: WOS:000369212900001
  article-title: Recent Advances in C-H Functionalization
  publication-title: JOURNAL OF ORGANIC CHEMISTRY
  doi: 10.1021/acs.joc.5b02818
  contributor:
    fullname: Davies, HML
– start-page: 3382
  year: 2006
  ident: WOS:000243569000002
  article-title: Regioselective functionalization of unreactive carbon-hydrogen bonds
  publication-title: SYNLETT
  doi: 10.1055/s-2006-956468
  contributor:
    fullname: Daugulis, O
– start-page: 2833
  year: 2007
  ident: WOS:000251507000013
  article-title: [RuCl3(H2O)(n)]-catalyzed direct arylations with bromides as electrophiles
  publication-title: SYNLETT
  doi: 10.1055/s-2007-990838
  contributor:
    fullname: Ackermann, L
– volume: 49
  start-page: 781
  year: 2010
  ident: WOS:000274424000022
  article-title: Room Temperature C-H Activation and Cross-Coupling of Aryl Ureas in Water
  publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
  doi: 10.1002/anie.200905967
  contributor:
    fullname: Nishikata, T
– volume: 15
  start-page: 1
  year: 2011
  ident: WOS:000287503600001
  article-title: Development of Ceria-Supported Ruthenium Catalysts Effective for Various Synthetic Reactions
  publication-title: CATALYSIS SURVEYS FROM ASIA
  doi: 10.1007/s10563-010-9104-6
  contributor:
    fullname: Wada, K
– volume: 68
  start-page: 5179
  year: 2012
  ident: WOS:000305381700010
  article-title: Catalytic C-H bond arylation of aryl imines and oxazolines in water with ruthenium(II)-acetate catalyst
  publication-title: TETRAHEDRON
  doi: 10.1016/j.tet.2012.03.117
  contributor:
    fullname: Li, B
– year: 2014
  ident: 000445711200009.3
  article-title: Ruthenium-Ctalyzed Synthesis of Biaryl Compounds in Water
  publication-title: PCT application
– year: 2007
  ident: 000445711200009.1
  article-title: Synthesis of a biaryl synthetic intermediate.
  publication-title: PCT application US
– volume: 102
  start-page: 1359
  year: 2002
  ident: WOS:000175550000003
  article-title: Aryl-aryl bond formation one century after the discovery of the Ullmann reaction
  publication-title: CHEMICAL REVIEWS
  doi: 10.1021/cr000664r
  contributor:
    fullname: Hassan, J
– volume: 103
  start-page: 893
  year: 2003
  ident: WOS:000181603000008
  article-title: The combinatorial synthesis of bicyclic privileged structures or privileged substructures
  publication-title: CHEMICAL REVIEWS
  doi: 10.1021/cr020033s
  contributor:
    fullname: Horton, DA
– volume: 41
  start-page: 59
  year: 2008
  ident: WOS:000260725100001
  article-title: Transition-Metal-Catalyzed Cross-Couplings Going Green: in Water at Room Temperature
  publication-title: ALDRICHIMICA ACTA
  contributor:
    fullname: Lipshutz, BH
– volume: 15
  start-page: 67
  year: 2013
  ident: WOS:000312545400004
  article-title: Ruthenium(II)-catalyzed selective monoarylation in water and sequential functionalisations of C-H bonds
  publication-title: GREEN CHEMISTRY
  doi: 10.1039/c2gc36222h
  contributor:
    fullname: Arockiam, PB
– volume: 133
  start-page: 10161
  year: 2011
  ident: WOS:000292715600044
  article-title: Autocatalysis for C-H Bond Activation by Ruthenium(II) Complexes in Catalytic Arylation of Functional Arenes
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  doi: 10.1021/ja201462n
  contributor:
    fullname: Flegeau, EF
– year: 2016
  ident: 000445711200009.2
  article-title: Ruthenium-Ctalyzed Synthesis of Biaryl Compounds in Water.
  publication-title: PCT application US
– volume: 14
  start-page: 2146
  year: 2012
  ident: WOS:000302990100050
  article-title: Well-Defined Ruthenium(II) Carboxylate as Catalyst for Direct C-H/C-O Bond Arylations with Phenols in Water
  publication-title: ORGANIC LETTERS
  doi: 10.1021/ol300671y
  contributor:
    fullname: Ackermann, L
– volume: 9
  start-page: 3380
  year: 2017
  ident: WOS:000409878300016
  article-title: Synthesis and Reactivity of 2-Arylquinazoline Halidoruthenacycles in Arylation Reactions
  publication-title: CHEMCATCHEM
  doi: 10.1002/cctc.201700494
  contributor:
    fullname: Kuzman, P
– volume: 48
  start-page: 5094
  year: 2009
  ident: WOS:000267809800005
  article-title: Palladium(II)-Catalyzed C-H Activation/C-C Cross-Coupling Reactions: Versatility and Practicality
  publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
  doi: 10.1002/anie.200806273
  contributor:
    fullname: Chen, X
– volume: 69
  start-page: 4445
  year: 2013
  ident: WOS:000318457900013
  article-title: Carboxylate-assisted ruthenium(II)-catalyzed C-H arylations of 5-aryl tetrazoles: step-economical access to Valsartan
  publication-title: TETRAHEDRON
  doi: 10.1016/j.tet.2013.01.006
  contributor:
    fullname: Diers, E
– volume: 11
  start-page: 2377
  year: 2009
  ident: WOS:000266546300039
  article-title: Amination of Allylic Alcohols in Water at Room Temperature
  publication-title: ORGANIC LETTERS
  doi: 10.1021/ol900235s
  contributor:
    fullname: Nishikata, T
– volume: 5
  start-page: 62
  year: 2008
  ident: WOS:000254018300049
  article-title: The concrete conundrum
  publication-title: CHEMISTRY WORLD
  contributor:
    fullname: Crow, JM
– volume: 12
  start-page: 5032
  year: 2010
  ident: WOS:000283531000083
  article-title: Mechanistic Insight into Direct Arylations with Ruthenium(II) Carboxylate Catalysts
  publication-title: ORGANIC LETTERS
  doi: 10.1021/ol102187e
  contributor:
    fullname: Ackermann, L
– volume: 7
  start-page: 5721
  year: 2017
  ident: WOS:000410005700019
  article-title: Recent Developments in Ruthenium-Catalyzed C-H Arylation: Array of Mechanistic Manifolds
  publication-title: ACS CATALYSIS
  doi: 10.1021/acscatal.7b01645
  contributor:
    fullname: Nareddy, P
– volume: 77
  start-page: 313
  year: 1977
  ident: WOS:A1977DG76500002
  article-title: STERIC EFFECTS OF PHOSPHORUS LIGANDS IN ORGANOMETALLIC CHEMISTRY AND HOMOGENEOUS CATALYSIS
  publication-title: CHEMICAL REVIEWS
  contributor:
    fullname: TOLMAN, CA
– volume: 2011
  start-page: 3474
  year: 2011
  ident: WOS:000293133100012
  article-title: C-H Bond Functionalization of Arylpyrimidines Catalyzed by an in situ Generated Ruthenium(II) Carboxylate System and the Construction of Tris(heteroaryl)-Substituted Benzenes
  publication-title: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
  doi: 10.1002/ejoc.201100238
  contributor:
    fullname: Stefane, B
– volume: 64
  start-page: 6115
  year: 2008
  ident: WOS:000256937700016
  article-title: [RuCl3(H2O)(n)]-catalyzed direct arylations
  publication-title: TETRAHEDRON
  doi: 10.1016/j.tet.2008.01.050
  contributor:
    fullname: Ackermann, L
– volume: 131
  start-page: 3104
  year: 2009
  ident: WOS:000264792300069
  article-title: Cross-Coupling Reactions of Aromatic and Heteroaromatic Silanolates with Aromatic and Heteroaromatic Halides
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  doi: 10.1021/ja8091449
  contributor:
    fullname: Denmark, SE
– volume: 76
  start-page: 1436
  year: 2011
  ident: WOS:000287636200024
  article-title: Preparative Scale Synthesis of the Biaryl Core of Anacetrapib via a Ruthenium-Catalyzed Direct Arylation Reaction: Unexpected Effect of Solvent Impurity on the Arylation Reaction
  publication-title: JOURNAL OF ORGANIC CHEMISTRY
  doi: 10.1021/jo1018574
  contributor:
    fullname: Ouellet, SG
– volume: 8
  start-page: 886
  year: 2018
  ident: WOS:000424735000018
  article-title: Sequential meta-/ortho-C-H Functionalizations by One-Pot Ruthenium(I/III) Catalysis
  publication-title: ACS CATALYSIS
  doi: 10.1021/acscatal.7b03648
  contributor:
    fullname: Korvorapun, K
– volume: 110
  start-page: 1147
  year: 2010
  ident: WOS:000274705900016
  article-title: Palladium-Catalyzed Ligand-Directed C-H Functionalization Reactions
  publication-title: CHEMICAL REVIEWS
  doi: 10.1021/cr900184e
  contributor:
    fullname: Lyons, TW
– volume: 10
  start-page: 5043
  year: 2008
  ident: WOS:000260534500084
  article-title: Dehydrative Direct Arylations of Arenes with Phenols via Ruthenium-Catalyzed C-H and C-OH Bond Functionalizations
  publication-title: ORGANIC LETTERS
  doi: 10.1021/ol802252m
  contributor:
    fullname: Ackermann, L
– start-page: 2245
  year: 2010
  ident: WOS:000280299200019
  article-title: Ruthenium-Catalyzed C-H Bond Functionalizations of 1,2,3-Triazol-4-yl-Substituted Arenes: Dehydrogenative Couplings Versus Direct Arylations
  publication-title: SYNTHESIS-STUTTGART
  doi: 10.1055/s-0029-1220010
  contributor:
    fullname: Ackermann, L
– volume: 70
  start-page: 3113
  year: 2005
  ident: WOS:000228367100026
  article-title: Ortho-selective direct cross-coupling reaction of 2-aryloxazolines and 2-arylimidazolines with aryl and alkenyl halides catalyzed by ruthenium complexes
  publication-title: JOURNAL OF ORGANIC CHEMISTRY
  doi: 10.1021/jo050031i
  contributor:
    fullname: Oi, S
– volume: 11
  start-page: 1871
  year: 2009
  ident: WOS:000271476500026
  article-title: Diethyl carbonate as a solvent for ruthenium catalysed C-H bond functionalisation
  publication-title: GREEN CHEMISTRY
  doi: 10.1039/b913115a
  contributor:
    fullname: Arockiam, P
– volume: 47
  start-page: 281
  year: 2014
  ident: WOS:000331775200001
  article-title: Carboxylate-Assisted Ruthenium-Catalyzed Alkyne Annulations by C-H/Het-H Bond Functionalizations
  publication-title: ACCOUNTS OF CHEMICAL RESEARCH
  doi: 10.1021/ar3002798
  contributor:
    fullname: Ackermann, L
– volume: 46
  start-page: 6364
  year: 2007
  ident: WOS:000249114700031
  article-title: Ruthenium(IV) alkylidenes as precatalysts for direct arylations of Alkenes with aryl chlorides and an application to sequential catalysis
  publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
  doi: 10.1002/anie.200701727
  contributor:
    fullname: Ackermann, L
– volume: 128
  start-page: 3508
  year: 2006
  ident: WOS:000236299700019
  article-title: Highly active water-soluble olefin metathesis catalyst
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  doi: 10.1021/ja058451c
  contributor:
    fullname: Hong, SH
– volume: 2
  start-page: 2424
  year: 2012
  ident: WOS:000310950000003
  article-title: Highly active catalysts for olefin metathesis in water
  publication-title: CATALYSIS SCIENCE & TECHNOLOGY
  doi: 10.1039/c2cy20320k
  contributor:
    fullname: Skowerski, K
– volume: 44
  start-page: 3275
  year: 2005
  ident: WOS:000229516300022
  article-title: "On water": Unique reactivity of organic compounds in aqueous suspension
  publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
  doi: 10.1002/anie.200462883
  contributor:
    fullname: Narayan, S
– volume: 3
  start-page: 2579
  year: 2001
  ident: WOS:000170392300041
  article-title: Ruthenium complex-catalyzed direct ortho arylation and alkenylation of 2-arylpyridines with organic halides
  publication-title: ORGANIC LETTERS
  doi: 10.1021/ol016257z
  contributor:
    fullname: Oi, S
– volume: 11
  start-page: 125
  year: 2004
  ident: CCC:000223893900005
  article-title: Ruthenium vinylidenes and allenylidenes in catalysis
  publication-title: RUTHENIUM CATALYSTS AND FINE CHEMISTRY
  contributor:
    fullname: Bruneau, C
– volume: 135
  start-page: 5877
  year: 2013
  ident: WOS:000317872800053
  article-title: meta-Selective C-H Bond Alkylation with Secondary Alkyl Halides
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  doi: 10.1021/ja401466y
  contributor:
    fullname: Hofmann, N
– year: 2005
  ident: 000445711200009.48
  publication-title: Ruthenium in Organic Synthesis
  contributor:
    fullname: Murahashi, S.-I.
– volume: 10
  start-page: 271
  year: 2008
  ident: WOS:000253751400003
  article-title: Olefin metathesis in water using acoustic emulsification
  publication-title: GREEN CHEMISTRY
  doi: 10.1039/b719493e
  contributor:
    fullname: Gulajski, L
– volume: 110
  start-page: 624
  year: 2010
  ident: WOS:000274705900003
  article-title: Rhodium-Catalyzed C-C Bond Formation via Heteroatom-Directed C-H Bond Activation
  publication-title: CHEMICAL REVIEWS
  doi: 10.1021/cr900005n
  contributor:
    fullname: Colby, DA
– volume: 112
  start-page: 5879
  year: 2012
  ident: WOS:000311239600009
  article-title: Ruthenium(II)-Catalyzed C-H Bond Activation and Functionalization
  publication-title: CHEMICAL REVIEWS
  doi: 10.1021/cr300153J
  contributor:
    fullname: Arockiam, PB
– volume: 45
  start-page: 2900
  year: 2016
  ident: WOS:000376520800009
  article-title: Mild metal-catalyzed C-H activation: examples and concepts
  publication-title: CHEMICAL SOCIETY REVIEWS
  doi: 10.1039/c6cs00075d
  contributor:
    fullname: Gensch, T
– volume: 11
  start-page: 4922
  year: 2009
  ident: WOS:000271097100040
  article-title: Catalytic Direct Arylations in Polyethylene Glycol (PEG): Recyclable Palladium(0) Catalyst for C-H Bond Cleavages in the Presence of Air
  publication-title: ORGANIC LETTERS
  doi: 10.1021/ol9020354
  contributor:
    fullname: Ackermann, L
– volume: 45
  start-page: 814
  year: 2012
  ident: WOS:000305321100005
  article-title: Rhodium Catalyzed Chelation-Assisted C-H Bond Functionalization Reactions
  publication-title: ACCOUNTS OF CHEMICAL RESEARCH
  doi: 10.1021/ar200190g
  contributor:
    fullname: Colby, DA
– volume: 57
  start-page: 62
  year: 2018
  ident: WOS:000418798600006
  article-title: Complementary Strategies for Directed C(sp(3))-H Functionalization: A Comparison of Transition-Metal-Catalyzed Activation, Hydrogen Atom Transfer, and Carbene/Nitrene Transfer
  publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
  doi: 10.1002/anie.201703743
  contributor:
    fullname: Chu, JCK
– volume: 86
  start-page: 32
  year: 2008
  ident: WOS:000253881800035
  article-title: Dennis reilley to receive SCI medal
  publication-title: CHEMICAL & ENGINEERING NEWS
  contributor:
    fullname: Reisch, MS
– volume: 49
  start-page: 6629
  year: 2010
  ident: WOS:000282477500032
  article-title: C-H Bond Functionalization in Water Catalyzed by Carboxylato Ruthenium(II) Systems
  publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
  doi: 10.1002/anie.201002870
  contributor:
    fullname: Arockiam, PB
– volume: 59
  start-page: 4443
  year: 2016
  ident: WOS:000376840600003
  article-title: Analysis of Past and Present Synthetic Methodologies on Medicinal Chemistry: Where Have All the New Reactions Gone?
  publication-title: JOURNAL OF MEDICINAL CHEMISTRY
  doi: 10.1021/acs.jmedchem.5b01409
  contributor:
    fullname: Brow, DG
– volume: 46
  start-page: 2577
  year: 2005
  ident: WOS:000228115600011
  article-title: A neutral, water-soluble olefin metathesis catalyst based on an N-heterocyclic carbene ligand
  publication-title: TETRAHEDRON LETTERS
  doi: 10.1016/j.tetlet.2005.02.096
  contributor:
    fullname: Gallivan, JP
– volume: 19
  start-page: 260
  year: 2015
  ident: WOS:000348332000024
  article-title: Robust Ruthenium(II)-Catalyzed C-H Arylations: Carboxylate Assistance for the Efficient Synthesis of Angiotensin-II-Receptor Blockers
  publication-title: ORGANIC PROCESS RESEARCH & DEVELOPMENT
  doi: 10.1021/op500330g
  contributor:
    fullname: Ackermann, L
– volume: 7
  start-page: 1380
  year: 2018
  ident: WOS:000438338100032
  article-title: Ruthenium-Catalyzed Intramolecular Hydroarylation of Arenes with Olefins in Water
  publication-title: ASIAN JOURNAL OF ORGANIC CHEMISTRY
  doi: 10.1002/ajoc.201800241
  contributor:
    fullname: Mukherjee, K
– volume: 15
  start-page: 2317
  year: 2013
  ident: WOS:000323179000001
  article-title: Olefin metathesis in aqueous media
  publication-title: GREEN CHEMISTRY
  doi: 10.1039/c3gc41042k
  contributor:
    fullname: Tomasek, J
– volume: 23
  start-page: ARTN 647
  year: 2018
  ident: WOS:000428514100138
  article-title: Ruthenium(n6,n1-arene-CH2-NHC) Catalysts for Direct Arylation of 2-Phenylpyridine with (Hetero)Aryl Chlorides in Water
  publication-title: MOLECULES
  doi: 10.3390/molecules23030647
  contributor:
    fullname: Kaloglu, N
– volume: 130
  start-page: 5858
  year: 2008
  ident: WOS:000255629400014
  article-title: Iron-catalyzed direct arylation through directed C-H bond activation
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  contributor:
    fullname: Norinder, J
– year: 2007
  ident: 000445711200009.4
  article-title: Synthesis of a biaryl synthetic intermediate.
  publication-title: PCT application WO
– volume: 10
  start-page: 2299
  year: 2008
  ident: WOS:000256281600053
  article-title: Assisted ruthenium-catalyzed C-H bond activation: Carboxylic acids as cocatalysts for generally applicable direct arylations in apolar solvents
  publication-title: ORGANIC LETTERS
  doi: 10.1021/ol800773x
  contributor:
    fullname: Ackermann, L
– ident: ref7/cit7
  doi: 10.1021/jo1018574
– ident: ref2/cit2e
  doi: 10.1021/ar3002798
– ident: ref4/cit4i
  doi: 10.1039/C2GC36222H
– ident: ref9/cit9
  doi: 10.1021/jo050031i
– ident: ref11/cit11
  doi: 10.1021/ja800818b
– ident: ref4/cit4d
  doi: 10.1021/ol300671y
– ident: ref4/cit4a
  doi: 10.1002/anie.201002870
– ident: ref4/cit4k
  doi: 10.1021/ja201462n
– ident: ref1/cit1h
  doi: 10.1039/b805701j
– ident: ref2/cit2t
  doi: 10.1021/ol800773x
– ident: ref2/cit2n
  doi: 10.1055/s-2007-990838
– ident: ref2/cit2r
  doi: 10.1016/j.tet.2013.01.006
– ident: ref12/cit12
  doi: 10.1007/s10563-010-9104-6
– ident: ref3/cit3e
  doi: 10.1039/c2cy20320k
– ident: ref4/cit4j
  doi: 10.1016/j.tet.2012.03.117
– ident: ref1/cit1i
  doi: 10.1039/C6CS00075D
– ident: ref2/cit2j
  doi: 10.3390/molecules23030647
– ident: ref2/cit2p
  doi: 10.1002/anie.200701727
– ident: ref8/cit8a
– ident: ref2/cit2q
  doi: 10.1002/ejoc.201100238
– ident: ref10/cit10b
  doi: 10.1055/s-2006-956468
– ident: ref3/cit3d
  doi: 10.1039/c3gc41042k
– ident: ref3/cit3h
  doi: 10.1016/j.tetlet.2005.02.096
– ident: ref8/cit8b
  doi: 10.1021/cen-v086n029.p032
– ident: ref1/cit1g
  doi: 10.1021/acs.joc.5b02818
– ident: ref4/cit4f
  doi: 10.1021/ja401466y
– ident: ref5/cit5
– ident: ref3/cit3g
  doi: 10.1039/b719493e
– ident: ref4/cit4g
  doi: 10.1002/anie.200905967
– start-page: 62
  year: 2008
  ident: ref3/cit3b
  publication-title: Chemistry World
  contributor:
    fullname: Crow J. M.
– ident: ref1/cit1f
  doi: 10.1002/anie.201703743
– ident: ref2/cit2f
  doi: 10.1021/acscatal.7b03648
– ident: ref2/cit2o
  doi: 10.1016/j.tet.2008.01.050
– ident: ref3/cit3j
  doi: 10.1021/ol051216e
– ident: ref3/cit3c
  doi: 10.1002/anie.200462883
– volume-title: Ruthenium in Organic Synthesis
  year: 2005
  ident: ref2/cit2g
  contributor:
    fullname: Murahashi S.-I.
– volume: 4
  start-page: 59
  year: 2008
  ident: ref3/cit3f
  publication-title: Aldrichimica Acta
  contributor:
    fullname: Lipshutz B. H.
– ident: ref2/cit2l
  doi: 10.1021/cr900005n
– ident: ref1/cit1c
  doi: 10.1021/acscatal.7b01645
– ident: ref1/cit1b
  doi: 10.1021/cr020033s
– ident: ref1/cit1d
  doi: 10.1021/acs.jmedchem.5b01409
– ident: ref3/cit3k
  doi: 10.1002/cctc.201700494
– ident: ref3/cit3a
– ident: ref2/cit2k
  doi: 10.1021/ar200190g
– volume: 7
  start-page: 1380
  year: 2018
  ident: ref2/cit2u
  publication-title: Asian J. Org. Chem.
  doi: 10.1002/ajoc.201800241
  contributor:
    fullname: Mukherjee K.
– ident: ref4/cit4h
  doi: 10.1021/ol900235s
– ident: ref2/cit2s
  doi: 10.1021/ol802252m
– ident: ref2/cit2a
  doi: 10.1002/anie.200806273
– ident: ref4/cit4f2
  doi: 10.1021/op500330g
– ident: ref2/cit2m
  doi: 10.1021/cr60307a002
– ident: ref2/cit2b
  doi: 10.1021/cr900184e
– ident: ref2/cit2c
  doi: 10.1021/cr300153j
– ident: ref2/cit2d
  doi: 10.1016/j.tet.2012.03.117
– ident: ref1/cit1a
  doi: 10.1021/cr000664r
– ident: ref4/cit4c
  doi: 10.1021/ol102187e
– ident: ref4/cit4e
  doi: 10.1021/ol9020354
– ident: ref10/cit10a
  doi: 10.1021/ol016257z
– ident: ref3/cit3i
  doi: 10.1021/ja058451c
– ident: ref10/cit10c
  doi: 10.1021/ol051216e
– ident: ref2/cit2i
  doi: 10.1021/acscatal.7b01645
– ident: ref2/cit2h
  doi: 10.1007/b10989
– ident: ref4/cit4l
  doi: 10.1039/b913115a
– ident: ref1/cit1e
  doi: 10.1021/ja8091449
– ident: ref4/cit4b
  doi: 10.1055/s-0029-1220010
SSID ssj0005612
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Snippet A new water friendly MCAT-53 [Ru2Cl2 (HCOO)3(p-cymene)] Na (sodium η-6-p-cymene dichloro diruthenium triformato complex) has been developed as a catalyst to...
A new water friendly MCAT-53 [Ru2Cl2 (HCOO)(3)(p-cymene)] Na (sodium eta-6-p-cymene dichloro diruthenium triformato complex) has been developed as a catalyst...
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SubjectTerms Chemistry
Chemistry, Applied
Chemistry, Organic
Physical Sciences
Science & Technology
Title Arene Ruthenium Catalyst MCAT-53 for the Synthesis of Heterobiaryl Compounds in Water through Aromatic C–H Bond Activation
URI http://dx.doi.org/10.1021/acs.oprd.8b00141
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