An Efficient Rh/O2 Catalytic System for Oxidative C–H Activation/Annulation: Evidence for Rh(I) to Rh(III) Oxidation by Molecular Oxygen
A novel and efficient Rh/O2 catalytic system has been developed and shown to catalyze highly efficient oxidative C–H activation/annulation reactions, producing a broad range of isoquinolinium salts with high turnover numbers (up to 740). Mechanistic studies provided strong evidence of facile oxidati...
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| Published in | Journal of the American Chemical Society Vol. 135; no. 24; pp. 8850 - 8853 |
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| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
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American Chemical Society
19.06.2013
Amer Chemical Soc |
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| Abstract | A novel and efficient Rh/O2 catalytic system has been developed and shown to catalyze highly efficient oxidative C–H activation/annulation reactions, producing a broad range of isoquinolinium salts with high turnover numbers (up to 740). Mechanistic studies provided strong evidence of facile oxidation of Rh(I) to Rh(III) by molecular oxygen facilitated by acid. |
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| AbstractList | A novel and efficient Rh/O2 catalytic system has been developed and shown to catalyze highly efficient oxidative C-H activation/annulation reactions, producing a broad range of isoquinolinium salts with high turnover numbers (up to 740). Mechanistic studies provided strong evidence of facile oxidation of Rh(I) to Rh(III) by molecular oxygen facilitated by acid. A novel and efficient Rh/O-2 catalytic system has been developed and shown to catalyze highly efficient oxidative C-H activation/annulation reactions, producing a broad range of isoquinolinium salts with high turnover numbers (up to 740). Mechanistic studies provided strong evidence of facile oxidation of Rh(I) to Rh(III) by molecular oxygen facilitated by acid. A novel and efficient Rh/O2 catalytic system has been developed and shown to catalyze highly efficient oxidative C-H activation/annulation reactions, producing a broad range of isoquinolinium salts with high turnover numbers (up to 740). Mechanistic studies provided strong evidence of facile oxidation of Rh(I) to Rh(III) by molecular oxygen facilitated by acid.A novel and efficient Rh/O2 catalytic system has been developed and shown to catalyze highly efficient oxidative C-H activation/annulation reactions, producing a broad range of isoquinolinium salts with high turnover numbers (up to 740). Mechanistic studies provided strong evidence of facile oxidation of Rh(I) to Rh(III) by molecular oxygen facilitated by acid. A novel and efficient Rh/O₂ catalytic system has been developed and shown to catalyze highly efficient oxidative C–H activation/annulation reactions, producing a broad range of isoquinolinium salts with high turnover numbers (up to 740). Mechanistic studies provided strong evidence of facile oxidation of Rh(I) to Rh(III) by molecular oxygen facilitated by acid. |
| Author | Zhang, Guoying Huang, Hanmin Yang, Lei Wang, Yanyu Xie, Yinjun |
| AuthorAffiliation | Chinese Academy of Sciences |
| AuthorAffiliation_xml | – name: Chinese Academy of Sciences |
| Author_xml | – sequence: 1 givenname: Guoying surname: Zhang fullname: Zhang, Guoying – sequence: 2 givenname: Lei surname: Yang fullname: Yang, Lei – sequence: 3 givenname: Yanyu surname: Wang fullname: Wang, Yanyu – sequence: 4 givenname: Yinjun surname: Xie fullname: Xie, Yinjun – sequence: 5 givenname: Hanmin surname: Huang fullname: Huang, Hanmin email: hmhuang@licp.cas.cn |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/23742052$$D View this record in MEDLINE/PubMed |
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| Cites_doi | 10.1021/jo070735n 10.1021/ar800042p 10.1002/anie.201200271 10.1002/anie.201101009 10.1002/anie.201105755 10.1246/cl.2010.744 10.1021/ja1067993 10.1021/cr0509760 10.1002/chem.201001363 10.1021/ja108668h 10.1021/ja102571b 10.1021/ol070406h 10.1021/ja802415h 10.1021/ar2002045 10.1021/ol070773t 10.1021/ja907198n 10.1021/ja806955s 10.1021/ja3030824 10.1002/chem.201300155 10.1002/ejoc.201001373 10.1002/anie.201101943 10.1021/cr900096x 10.1021/jo1021184 10.1021/ol102504b 10.1002/anie.200806273 10.1021/ol1030298 10.1002/anie.200700604 10.1002/anie.200801240 10.1039/c1cc13632a 10.1021/ja904380q 10.1039/b910198e 10.1021/cr900269x 10.1021/ja105044s 10.1021/jo200897q 10.1039/c2cy20111a 10.1002/anie.201100229 10.1021/cr900184e 10.1021/ol100560k 10.1021/ja049962m 10.1002/chem.201300922 10.1002/anie.200604045 10.1021/cr050523v 10.1021/ja110650m 10.1021/ja103776u 10.1021/ja201143v 10.1021/ol400307d 10.1021/ol301445r 10.1002/anie.200801009 10.1021/cr100198w 10.1021/ar3000508 10.1021/ja7112504 10.1021/cr900005n 10.1002/anie.200700515 10.1002/adsc.201200944 10.1002/anie.200351524 10.1021/cr300153J 10.1021/ja104305s 10.1021/cr0104330 10.1002/anie.201301165 10.1002/anie.201003646 10.1021/ja303333k 10.1002/anie.200300630 10.1039/b905275e 10.1002/chem.201203374 10.1002/chem.200902374 10.1021/cr100412j 10.1039/b902868d 10.1021/ja1082624 10.1021/jo301741j 10.1021/cr050980b 10.1002/anie.200800924 10.1039/c2cs15224j |
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| Keywords | FUNCTIONALIZATION ACTIVATION COUPLING REACTIONS RHODIUM(III)-CATALYZED SYNTHESIS TERTIARY-AMINES RH BOND FORMATION INTERNAL ALKYNES ISOQUINOLINIUM SALTS BENZOIC-ACIDS |
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| References | Dams, M (WOS:000184761500012) 2003; 42 Nunez, A (WOS:000248315900005) 2007; 9 Punniyamurthy, T (WOS:000229729000012) 2005; 105 Muralirajan, K (WOS:000290662500023) 2011; 50 Zhao, DB (WOS:000318365200011) 2013; 19 Nuñez, A (WOS:000288128600010) 2011; 2011 Colby, DA (WOS:000274705900003) 2010; 110 Zhang, G (WOS:000306942600004) 2012; 134 Herrerias, CI (WOS:000247217000014) 2007; 107 Umeda, N (WOS:000285704000002) 2011; 76 Stahl, SS (WOS:000222428800004) 2004; 43 Too, PC (WOS:000293252600030) 2011; 76 Ueura, K (WOS:000247612200041) 2007; 72 Fortage, J (WOS:000284792000063) 2010; 132 Ritleng, V (WOS:000175550000011) 2002; 102 Guimond, N (WOS:000269379600015) 2009; 131 Stuart, DR (WOS:000285818700052) 2010; 132 Ueda, S (WOS:000258584800017) 2008; 47 Ueura, K (WOS:000245084300059) 2007; 9 Morimoto, K (WOS:000277212800045) 2010; 12 Patureau, FW (WOS:000287909200039) 2011; 133 Gunay, A (WOS:000274705900014) 2010; 110 Yang, L (WOS:000304106900002) 2012; 2 Ackermann, L (WOS:000288820600005) 2011; 111 Wang, NC (WOS:000313157200037) 2013; 19 Guimond, N (WOS:000277999700021) 2010; 132 Umeda, N (WOS:000255994700035) 2008; 47 Baslé, O (WOS:000267571100039) 2009 Campbell, AN (WOS:000305321100008) 2012; 45 Fukutani, T (WOS:000269081900021) 2009 Muralirajan, K (WOS:000318365200002) 2013; 19 Too, PC (WOS:000285081300024) 2010; 12 Jayakumar, J (WOS:000298598500031) 2012; 51 Wang, HG (WOS:000318370200036) 2013; 52 Campbell, AN (WOS:000294500600015) 2011; 47 Wei, Y (WOS:000304837800020) 2012; 134 Engle, KM (WOS:000282660100052) 2010; 132 Hyster, TK (WOS:000280456100055) 2010; 132 Li, L (WOS:000259139900055) 2008; 130 Lewis, JC (WOS:000258580600013) 2008; 41 Alberico, D (WOS:000243381000008) 2007; 107 Sun, CL (WOS:000288820600004) 2011; 111 KRANE, BD (WOS:A1984SH41700001) 1984; 47 Jazzar, R (WOS:000275943000001) 2010; 16 Konnick, MM (WOS:000255360100042) 2008; 130 Arockiam, PB (WOS:000311239600009) 2012; 112 Mochida, S (WOS:000280243900035) 2010; 39 Lyons, TW (WOS:000274705900016) 2010; 110 Anthony, JE (WOS:000252452800004) 2008; 47 Chen, X (WOS:000267809800005) 2009; 48 Willis, MC (WOS:000274705900007) 2010; 110 Parthasarathy, K (WOS:000306050300062) 2012; 14 Piera, J (WOS:000255530100007) 2008; 47 Presset, M (WOS:000317327900028) 2013; 15 Satoh, T (WOS:000283386600001) 2010; 16 Gligorich, KM (WOS:000267299500002) 2009 Ackermann, L (WOS:000292642600033) 2011; 50 Wu, WQ (WOS:000309804700011) 2012; 45 Liu, GS (WOS:000256894600025) 2008; 47 Rakshit, S (WOS:000280086800026) 2010; 132 Wang, YF (WOS:000292001700028) 2011; 50 Wang, HG (WOS:000282304000044) 2010; 132 Guimond, N (WOS:000292715500050) 2011; 133 Li, BJ (WOS:000302607500037) 2012; 51 Shi, ZZ (WOS:000301985300020) 2012; 41 Xia, XF (WOS:000309951700033) 2012; 77 Steinhoff, BA (WOS:000223799900040) 2004; 126 Stuart, DR (WOS:000263320200016) 2008; 130 Wu, DQ (WOS:000248063200036) 2007; 46 Xie, YJ (WOS:000318762100014) 2013; 355 Tian, JS (WOS:000284015600022) 2010; 49 Zhang, YH (WOS:000271271800028) 2009; 131 Guo, SM (WOS:000286577600044) 2011; 13 |
| References_xml | – volume: 72 start-page: 5362 year: 2007 ident: WOS:000247612200041 article-title: Rhodium- and iridium-catalyzed oxidative coupling of benzoic acids with alkynes via regioselective C-H bond cleavage publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo070735n – volume: 41 start-page: 1013 year: 2008 ident: WOS:000258580600013 article-title: Direct functionalization of nitrogen heterocycles via Rh-catalyzed C-H bond activation publication-title: ACCOUNTS OF CHEMICAL RESEARCH doi: 10.1021/ar800042p – volume: 51 start-page: 3948 year: 2012 ident: WOS:000302607500037 article-title: Rhodium/Copper-Catalyzed Annulation of Benzimides with Internal Alkynes: Indenone Synthesis through Sequential C-H and C-N Cleavage publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201200271 – volume: 50 start-page: 5927 year: 2011 ident: WOS:000292001700028 article-title: Synthesis of Isoquinolines from α-Aryl Vinyl Azides and Internal Alkynes by Rh-Cu Bimetallic Cooperation publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201101009 – volume: 51 start-page: 197 year: 2012 ident: WOS:000298598500031 article-title: One-Pot Synthesis of Isoquinolinium Salts by Rhodium-Catalyzed C-H Bond Activation: Application to the Total Synthesis of Oxychelerythrine publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201105755 – volume: 39 start-page: 744 year: 2010 ident: WOS:000280243900035 article-title: Rhodium-catalyzed Oxidative Coupling/Cyclization of Benzamides with Alkynes via C-H Bond Cleavage publication-title: CHEMISTRY LETTERS doi: 10.1246/cl.2010.744 – volume: 132 start-page: 13217 year: 2010 ident: WOS:000282304000044 article-title: Direct Intramolecular C-H Amination Reaction Cocatalyzed by Copper(II) and Iron(III) as Part of an Efficient Route for the Synthesis of Pyrido[1,2-a]benzimidazoles from N-Aryl-2-aminopyridines publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja1067993 – volume: 107 start-page: 174 year: 2007 ident: WOS:000243381000008 article-title: Aryl-aryl bond formation by transition-metal-catalyzed direct arylation publication-title: CHEMICAL REVIEWS doi: 10.1021/cr0509760 – volume: 16 start-page: 11212 year: 2010 ident: WOS:000283386600001 article-title: Oxidative Coupling of Aromatic Substrates with Alkynes and Alkenes under Rhodium Catalysis publication-title: CHEMISTRY-A EUROPEAN JOURNAL doi: 10.1002/chem.201001363 – volume: 132 start-page: 16700 year: 2010 ident: WOS:000284792000063 article-title: Designing Multifunctional Expanded Pyridiniums: Properties of Branched and Fused Head-to-Tail Bipyridiniums publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja108668h – volume: 132 start-page: 6908 year: 2010 ident: WOS:000277999700021 article-title: Rhodium(III)-Catalyzed Isoquinolone Synthesis: The N-O Bond as a Handle for C-N Bond Formation and Catalyst Turnover publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja102571b – volume: 9 start-page: 1407 year: 2007 ident: WOS:000245084300059 article-title: An efficient waste-free oxidative coupling via regioselective C-H bond cleavage: Rh/Cu-catalyzed reaction of benzoic acids with alkynes and acrylates under air publication-title: ORGANIC LETTERS doi: 10.1021/ol070406h – volume: 130 start-page: 12414 year: 2008 ident: WOS:000259139900055 article-title: An efficient low-temperature route to polycyclic isoquinoline salt synthesis via C-H activation with [Cp☆MCl2]2 (M = Rh, Ir) publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja802415h – volume: 45 start-page: 851 year: 2012 ident: WOS:000305321100008 article-title: Overcoming the "Oxidant Problem": Strategies to Use O2 as the Oxidant in Organometallic C-H Oxidation Reactions Catalyzed by Pd (and Cu) publication-title: ACCOUNTS OF CHEMICAL RESEARCH doi: 10.1021/ar2002045 – volume: 9 start-page: 2977 year: 2007 ident: WOS:000248315900005 article-title: A new approach to polycyclic azonia cations by ring-closing metathesis publication-title: ORGANIC LETTERS doi: 10.1021/ol070773t – volume: 131 start-page: 14654 year: 2009 ident: WOS:000271271800028 article-title: Pd(II)-Catalyzed Hydroxylation of Arenes with 1 atm of O2 or Air publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja907198n – volume: 130 start-page: 16474 year: 2008 ident: WOS:000263320200016 article-title: Indole Synthesis via Rhodium Catalyzed Oxidative Coupling of Acetanilides and Internal Alkynes publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja806955s – volume: 134 start-page: 9098 year: 2012 ident: WOS:000304837800020 article-title: Palladium-Catalyzed Aerobic Oxidative Cyclization of N-Aryl lmines: lndole Synthesis from Anilines and Ketones publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja3030824 – volume: 47 start-page: 1 year: 1984 ident: WOS:A1984SH41700001 article-title: THE BENZOPHENANTHRIDINE ALKALOIDS publication-title: JOURNAL OF NATURAL PRODUCTS – volume: 19 start-page: 6239 year: 2013 ident: WOS:000318365200011 article-title: A General Method to Diverse Cinnolines and Cinnolinium Salts publication-title: CHEMISTRY-A EUROPEAN JOURNAL doi: 10.1002/chem.201300155 – volume: 2011 start-page: 1280 year: 2011 ident: WOS:000288128600010 article-title: Ring-Closing Metathesis Approach to Heteroaromatic Cations: Synthesis of Benzo[a]quinolizinium Salts publication-title: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY doi: 10.1002/ejoc.201001373 – volume: 50 start-page: 6379 year: 2011 ident: WOS:000292642600033 article-title: Ruthenium-Catalyzed Oxidative Annulation by Cleavage of C-H/N-H Bonds publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201101943 – volume: 110 start-page: 725 year: 2010 ident: WOS:000274705900007 article-title: Transition Metal Catalyzed Alkene and Alkyne Hydroacylation publication-title: CHEMICAL REVIEWS doi: 10.1021/cr900096x – volume: 76 start-page: 13 year: 2011 ident: WOS:000285704000002 article-title: Rhodium-Catalyzed Oxidative 1:1, 1:2, and 1:4 Coupling Reactions of Phenylazoles with Internal Alkynes through the Regioselective Cleavages of Multiple C-H Bonds publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo1021184 – volume: 12 start-page: 5688 year: 2010 ident: WOS:000285081300024 article-title: Rhodium(III)-Catalyzed Synthesis of Isoquinolines from Aryl Ketone O-Acyloxime Derivatives and Internal Alkynes publication-title: ORGANIC LETTERS doi: 10.1021/ol102504b – 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 – volume: 13 start-page: 522 year: 2011 ident: WOS:000286577600044 article-title: Copper-Catalyzed Oxidative Amination of Benzoxazoles via C-H and C-N Bond Activation: A New Strategy for Using Tertiary Amines as Nitrogen Group Sources publication-title: ORGANIC LETTERS doi: 10.1021/ol1030298 – volume: 47 start-page: 3506 year: 2008 ident: WOS:000255530100007 article-title: Catalytic oxidation of organic substrates by molecular oxygen and hydrogen peroxide by multistep electron transfer -: A biomimetic approach publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.200700604 – volume: 47 start-page: 6411 year: 2008 ident: WOS:000258584800017 article-title: Synthesis of 2-arylbenzoxazoles by copper-catalyzed intramolecular oxidative C-O coupling of benzanilides publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.200801240 – volume: 47 start-page: 10257 year: 2011 ident: WOS:000294500600015 article-title: Regiocontrolled aerobic oxidative coupling of indoles and benzene using Pd catalysts with 4,5-diazafluorene ligands publication-title: CHEMICAL COMMUNICATIONS doi: 10.1039/c1cc13632a – volume: 131 start-page: 12050 year: 2009 ident: WOS:000269379600015 article-title: Isoquinoline Synthesis via Rhodium-Catalyzed Oxidative Cross-Coupling/Cyclization of Aryl Aldimines and Alkynes publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja904380q – start-page: 5141 year: 2009 ident: WOS:000269081900021 article-title: Rhodium-catalyzed oxidative coupling of aromatic imines with internal alkynes via regioselective C-H bond cleavage publication-title: CHEMICAL COMMUNICATIONS doi: 10.1039/b910198e – volume: 110 start-page: 1060 year: 2010 ident: WOS:000274705900014 article-title: C-H Bond Activations by Metal Oxo Compounds publication-title: CHEMICAL REVIEWS doi: 10.1021/cr900269x – volume: 132 start-page: 14137 year: 2010 ident: WOS:000282660100052 article-title: Ligand-Accelerated C-H Activation Reactions: Evidence for a Switch of Mechanism publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja105044s – volume: 76 start-page: 6159 year: 2011 ident: WOS:000293252600030 article-title: Synthesis of Azaheterocycles from Aryl Ketone O-Acetyl Oximes and Internal Alkynes by Cu-Rh Bimetallic Relay Catalysts publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo200897q – volume: 2 start-page: 1099 year: 2012 ident: WOS:000304106900002 article-title: Asymmetric catalytic carbon-carbon coupling reactions via C-H bond activation publication-title: CATALYSIS SCIENCE & TECHNOLOGY doi: 10.1039/c2cy20111a – volume: 50 start-page: 4169 year: 2011 ident: WOS:000290662500023 article-title: Regioselective Synthesis of Indenols by Rhodium-Catalyzed C-H Activation and Carbocyclization of Aryl Ketones and Alkynes publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201100229 – 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 – volume: 12 start-page: 2068 year: 2010 ident: WOS:000277212800045 article-title: Rhodium-Catalyzed Oxidative Coupling/Cyclization of 2-Phenylindoles with Alkynes via C-H and N-H Bond Cleavages with Air as the Oxidant publication-title: ORGANIC LETTERS doi: 10.1021/ol100560k – volume: 126 start-page: 11268 year: 2004 ident: WOS:000223799900040 article-title: Mechanistic characterization of aerobic alcohol oxidation catalyzed by Pd(OAc)2/pyridine including identification of the catalyst resting state and the origin of nonlinear [catalyst] dependence publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja049962m – volume: 19 start-page: 6198 year: 2013 ident: WOS:000318365200002 article-title: Rhodium(III)-Catalyzed Synthesis of Cinnolinium Salts from Azobenzenes and Alkynes: Application to the Synthesis of Indoles and Cinnolines publication-title: CHEMISTRY-A EUROPEAN JOURNAL doi: 10.1002/chem.201300922 – volume: 47 start-page: 452 year: 2008 ident: WOS:000252452800004 article-title: The larger acenes: Versatile organic semiconductors publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.200604045 – volume: 105 start-page: 2329 year: 2005 ident: WOS:000229729000012 article-title: Recent advances in transition metal catalyzed oxidation of organic substrates with molecular oxygen publication-title: CHEMICAL REVIEWS doi: 10.1021/cr050523v – volume: 133 start-page: 2154 year: 2011 ident: WOS:000287909200039 article-title: Diverse Strategies toward Indenol and Fulvene Derivatives: Rh-Catalyzed C-H Activation of Aryl Ketones Followed by Coupling with Internal Alkynes publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja110650m – volume: 132 start-page: 10565 year: 2010 ident: WOS:000280456100055 article-title: Rhodium-Catalyzed Oxidative Cycloaddition of Benzamides and Alkynes via C-H/N-H Activation publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja103776u – volume: 133 start-page: 6449 year: 2011 ident: WOS:000292715500050 article-title: Rhodium(III)-Catalyzed Heterocycle Synthesis Using an Internal Oxidant: Improved Reactivity and Mechanistic Studies publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja201143v – volume: 15 start-page: 1528 year: 2013 ident: WOS:000317327900028 article-title: Complementary Regioselectivity in Rh(III)-Catalyzed Insertions of Potassium Vinyltrifluoroborate via C-H Activation: Preparation and Use of 4-Trifluoroboratotetrahydroisoquinolones publication-title: ORGANIC LETTERS doi: 10.1021/ol400307d – volume: 14 start-page: 3478 year: 2012 ident: WOS:000306050300062 article-title: Ru(II)-Catalyzed C-H Bond Activation for the Synthesis of Substituted Isoquinolinium Salts from Benzaldehydes, Amines, and Alkynes publication-title: ORGANIC LETTERS doi: 10.1021/ol301445r – volume: 47 start-page: 4733 year: 2008 ident: WOS:000256894600025 article-title: Palladium-catalyzed intermolecular aerobic oxidative amination of terminal alkenes: Efficient synthesis of linear allylamine derivatives publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.200801009 – volume: 111 start-page: 1293 year: 2011 ident: WOS:000288820600004 article-title: Direct C-H Transformation via Iron Catalysis publication-title: CHEMICAL REVIEWS doi: 10.1021/cr100198w – volume: 45 start-page: 1736 year: 2012 ident: WOS:000309804700011 article-title: Palladium-Catalyzed Oxidation of Unsaturated Hydrocarbons Using Molecular Oxygen publication-title: ACCOUNTS OF CHEMICAL RESEARCH doi: 10.1021/ar3000508 – volume: 130 start-page: 5753 year: 2008 ident: WOS:000255360100042 article-title: Reaction of molecular oxygen with a PdII-hydride to produce a PdII-hydroperoxide:: Experimental evidence for an HX-reductive-elimination pathway publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja7112504 – 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 – volume: 46 start-page: 5417 year: 2007 ident: WOS:000248063200036 article-title: Self-assembly of positively charged discotic PAHs:: From nanofibers to nanotubes publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.200700515 – volume: 355 start-page: 1315 year: 2013 ident: WOS:000318762100014 article-title: Cooperative Catalysis with Aldehydes and Copper: Development and Application in Aerobic Oxidative CH Amination at Room Temperature publication-title: ADVANCED SYNTHESIS & CATALYSIS doi: 10.1002/adsc.201200944 – volume: 42 start-page: 3512 year: 2003 ident: WOS:000184761500012 article-title: Toward waste-free production of Heck products with a catalytic palladium system under oxygen publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.200351524 – 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 – volume: 132 start-page: 9585 year: 2010 ident: WOS:000280086800026 article-title: Pyrrole Synthesis via Allylic sp3 C-H Activation of Enamines Followed by Intermolecular Coupling with Unactivated Alkynes publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja104305s – volume: 102 start-page: 1731 year: 2002 ident: WOS:000175550000011 article-title: Ru-, Rh-, and Pd-catalyzed C-C bond formation involving C-H activation and addition on unsaturated substrates: Reactions and mechanistic aspects publication-title: CHEMICAL REVIEWS doi: 10.1021/cr0104330 – volume: 52 start-page: 5386 year: 2013 ident: WOS:000318370200036 article-title: Mild Rhodium(III)-Catalyzed Direct C-H Allylation of Arenes with Allyl Carbonates publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201301165 – volume: 49 start-page: 8417 year: 2010 ident: WOS:000284015600022 article-title: Copper-Catalyzed Rearrangement of Tertiary Amines through Oxidation of Aliphatic C-H Bonds in Air or Oxygen: Direct Synthesis of α-Amino Acetals publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201003646 – volume: 134 start-page: 12334 year: 2012 ident: WOS:000306942600004 article-title: Enantioselective Metal/Organo-Catalyzed Aerobic Oxidative sp3 C-H Olefination of Tertiary Amines Using Molecular Oxygen as the Sole Oxidant publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja303333k – volume: 43 start-page: 3400 year: 2004 ident: WOS:000222428800004 article-title: Palladium oxidase catalysis: Selective oxidation of organic chemicals by direct dioxygen-coupled turnover publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.200300630 – start-page: 4124 year: 2009 ident: WOS:000267571100039 article-title: Copper-catalyzed aerobic phosphonation of sp3 C-H bonds publication-title: CHEMICAL COMMUNICATIONS doi: 10.1039/b905275e – volume: 19 start-page: 358 year: 2013 ident: WOS:000313157200037 article-title: Investigation and Comparison of the Mechanistic Steps in the [(Cp*MCl2)2] (Cp*=C5Me5; M = Rh, Ir)-Catalyzed Oxidative Annulation of Isoquinolones with Alkynes publication-title: CHEMISTRY-A EUROPEAN JOURNAL doi: 10.1002/chem.201203374 – volume: 16 start-page: 2654 year: 2010 ident: WOS:000275943000001 article-title: Functionalization of Organic Molecules by Transition-Metal-Catalyzed C(sp3)-H Activation publication-title: CHEMISTRY-A EUROPEAN JOURNAL doi: 10.1002/chem.200902374 – volume: 111 start-page: 1315 year: 2011 ident: WOS:000288820600005 article-title: Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope publication-title: CHEMICAL REVIEWS doi: 10.1021/cr100412j – start-page: 3854 year: 2009 ident: WOS:000267299500002 article-title: Recent advancements and challenges of palladiumII-catalyzed oxidation reactions with molecular oxygen as the sole oxidant publication-title: CHEMICAL COMMUNICATIONS doi: 10.1039/b902868d – volume: 132 start-page: 18326 year: 2010 ident: WOS:000285818700052 article-title: Rhodium(III)-Catalyzed Arene and Alkene C-H Bond Functionalization Leading to Indoles and Pyrroles publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja1082624 – volume: 77 start-page: 9163 year: 2012 ident: WOS:000309951700033 article-title: Palladium(II)-Catalyzed Tandem Cyclization/C-H Functionalization of Alkynes for the Synthesis of Functionalized Indoles publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo301741j – volume: 107 start-page: 2546 year: 2007 ident: WOS:000247217000014 article-title: Reactions of C-H bonds in water publication-title: CHEMICAL REVIEWS doi: 10.1021/cr050980b – volume: 47 start-page: 4019 year: 2008 ident: WOS:000255994700035 article-title: Fluorescent naphthyl- and anthrylazoles from the catalytic coupling of phenylazoles with internal alkynes through the cleavage of multiple, C-H bonds publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.200800924 – volume: 41 start-page: 3381 year: 2012 ident: WOS:000301985300020 article-title: Recent advances in transition-metal catalyzed reactions using molecular oxygen as the oxidant publication-title: CHEMICAL SOCIETY REVIEWS doi: 10.1039/c2cs15224j |
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| Snippet | A novel and efficient Rh/O2 catalytic system has been developed and shown to catalyze highly efficient oxidative C–H activation/annulation reactions, producing... A novel and efficient Rh/O-2 catalytic system has been developed and shown to catalyze highly efficient oxidative C-H activation/annulation reactions,... A novel and efficient Rh/O2 catalytic system has been developed and shown to catalyze highly efficient oxidative C-H activation/annulation reactions, producing... A novel and efficient Rh/O₂ catalytic system has been developed and shown to catalyze highly efficient oxidative C–H activation/annulation reactions, producing... |
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| SubjectTerms | Chemistry Chemistry, Multidisciplinary oxidation oxygen Physical Sciences salts Science & Technology |
| Title | An Efficient Rh/O2 Catalytic System for Oxidative C–H Activation/Annulation: Evidence for Rh(I) to Rh(III) Oxidation by Molecular Oxygen |
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