메뉴 건너뛰기




Volumn 55, Issue 10, 2012, Pages 2027-2035

Mechanistic aspects of oxidation of palladium with O 2

Author keywords

Mechanism; O 2; Palladium

Indexed keywords

AEROBIC OXIDATIONS; AEROBIC TRANSFORMATIONS; ALCOHOL OXIDATION; MECHANISTIC ASPECTS; MECHANISTIC STUDIES; OXIDATIVE COUPLINGS; PALLADIUM-CATALYZED;

EID: 84869094975     PISSN: 16747291     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11426-012-4719-2     Document Type: Conference Paper
Times cited : (25)

References (76)
  • 1
    • 24944468108 scopus 로고    scopus 로고
    • Palladium-catalyzed oxidation of organic chemicals with O2
    • Stahl SS. Palladium-catalyzed oxidation of organic chemicals with O2. Science, 2005, 309: 1824-1826
    • (2005) Science , vol.309 , pp. 1824-1826
    • Stahl, S.S.1
  • 2
    • 70149092833 scopus 로고    scopus 로고
    • Catalysis and sustainable development: The marriage for innovation
    • Beller M, Centi G. Catalysis and sustainable development: The marriage for innovation. ChemSusChem, 2009, 2: 459-460
    • (2009) ChemSusChem , vol.2 , pp. 459-460
    • Beller, M.1    Centi, G.2
  • 3
    • 21944440277 scopus 로고    scopus 로고
    • Recent advances in transition metal catalyzed oxidation of organic substrates with molecular oxygen
    • Punniyamurthy T, Velusamy S, Iqbal J. Recent advances in transition metal catalyzed oxidation of organic substrates with molecular oxygen. Chem Rev, 2005, 105: 2329-2364
    • (2005) Chem Rev , vol.105 , pp. 2329-2364
    • Punniyamurthy, T.1    Velusamy, S.2    Iqbal, J.3
  • 4
    • 84859132397 scopus 로고    scopus 로고
    • Recent advances in transition-metal catalyzed reactions using molecular oxygen as the oxidant
    • Shi Z, Zhang C, Tang C, Jiao N. Recent advances in transition-metal catalyzed reactions using molecular oxygen as the oxidant. Chem Soc Rev, 2012, 41: 3381-3430
    • (2012) Chem Soc Rev , vol.41 , pp. 3381-3430
    • Shi, Z.1    Zhang, C.2    Tang, C.3    Jiao, N.4
  • 5
    • 81255162913 scopus 로고    scopus 로고
    • Copper-catalyzed aerobic oxidative C-H functionalizations: Trends and mechanistic insights
    • Wendlandt AE, Suess AM, Stahl SS. Copper-catalyzed aerobic oxidative C-H functionalizations: Trends and mechanistic insights. Angew Chem Int Ed, 2011, 50: 11062-11087
    • (2011) Angew Chem Int Ed , vol.50 , pp. 11062-11087
    • Wendlandt, A.E.1    Suess, A.M.2    Stahl, S.S.3
  • 6
    • 79961143500 scopus 로고    scopus 로고
    • C-H oxidation by platinum group metal oxo or peroxo species
    • Zhou M, Crabtree R H. C-H oxidation by platinum group metal oxo or peroxo species. Chem Soc Rev, 2011, 40: 1875-1884
    • (2011) Chem Soc Rev , vol.40 , pp. 1875-1884
    • Zhou, M.1    Crabtree, R.H.2
  • 7
    • 0346471289 scopus 로고
    • Synthesis of unsymmetrical biaryls via kinetic higher order cyanocuprates: Scope, limitations, and spectroscopic insights
    • Lipshutz BH, Siegmann K, Garcia E, Kayser F. Synthesis of unsymmetrical biaryls via kinetic higher order cyanocuprates: Scope, limitations, and spectroscopic insights. J Am Chem Soc, 1993, 115: 9276-9282
    • (1993) J Am Chem Soc , vol.115 , pp. 9276-9282
    • Lipshutz, B.H.1    Siegmann, K.2    Garcia, E.3    Kayser, F.4
  • 8
    • 33845251381 scopus 로고    scopus 로고
    • Oxovanadium (V)-catalyzed oxidative biaryl synthesis from organoborate under O2
    • Mizuno H, Sakurai H, Amaya T, Hirao T. Oxovanadium(V)-catalyzed oxidative biaryl synthesis from organoborate under O2. Chem Commun, 2006: 5042-5044
    • (2006) Chem Commun , pp. 5042-5044
    • Mizuno, H.1    Sakurai, H.2    Amaya, T.3    Hirao, T.4
  • 9
    • 77950266691 scopus 로고    scopus 로고
    • Palladium-catalyzed aerobic oxidative cross-coupling reactions of terminal alkynes with alkylzinc reagents
    • Chen M, Zheng X, Li W, He J, Lei A. Palladium-catalyzed aerobic oxidative cross-coupling reactions of terminal alkynes with alkylzinc reagents. J Am Chem Soc, 2010, 132: 4101-4103
    • (2010) J Am Chem Soc , vol.132 , pp. 4101-4103
    • Chen, M.1    Zheng, X.2    Li, W.3    He, J.4    Lei, A.5
  • 10
    • 58849130239 scopus 로고    scopus 로고
    • Versatile Pd(II)-catalyzed C-H activation/ aryl-aryl coupling of benzoic and phenyl acetic acids
    • Wang D, Mei T, Yu J. Versatile Pd(II)-catalyzed C-H activation/ aryl-aryl coupling of benzoic and phenyl acetic acids. J Am Chem Soc, 2008, 130: 17676-17677
    • (2008) J Am Chem Soc , vol.130 , pp. 17676-17677
    • Wang, D.1    Mei, T.2    Yu, J.3
  • 11
    • 34547212729 scopus 로고    scopus 로고
    • Suzuki-Miyaura coupling reaction by Pd(II)-catalyzed aromatic C-H bond activation directed by an n-alkyl acetamino group
    • Shi Z, Li B, Wan X, Cheng J, Fang Z, Cao B, Qin C, Wang Y. Suzuki-Miyaura coupling reaction by Pd(II)-catalyzed aromatic C-H bond activation directed by an n-alkyl acetamino group. Angew Chem Int Ed, 2007, 46: 5554-5558
    • (2007) Angew Chem Int Ed , vol.46 , pp. 5554-5558
    • Shi, Z.1    Li, B.2    Wan, X.3    Cheng, J.4    Fang, Z.5    Cao, B.6    Qin, C.7    Wang, Y.8
  • 12
    • 33750516508 scopus 로고    scopus 로고
    • NHC-Pd(II) complex-Cu(I) co-catalyzed homocoupling reaction of terminal alkynes
    • Shi M, Qian H. NHC-Pd(II) complex-Cu(I) co-catalyzed homocoupling reaction of terminal alkynes. Appl Organomet Chem, 2006, 20: 771-774
    • (2006) Appl Organomet Chem , vol.20 , pp. 771-774
    • Shi, M.1    Qian, H.2
  • 13
    • 36549024883 scopus 로고    scopus 로고
    • An efficient and practical process for Pd/Cu cocatalyzedhomocoupling reaction of terminal alkynes using sodium percarbonate as a dual reagent in aqueous media
    • Zhou L, Zhan H, Liu H, Jiang H. An efficient and practical process for Pd/Cu cocatalyzedhomocoupling reaction of terminal alkynes using sodium percarbonate as a dual reagent in aqueous media. Chin J Chem, 2007, 25: 1413-1416
    • (2007) Chin J Chem , vol.25 , pp. 1413-1416
    • Zhou, L.1    Zhan, H.2    Liu, H.3    Jiang, H.4
  • 14
    • 67649449350 scopus 로고    scopus 로고
    • Homocoupling reaction of terminal alkynes catalyzed by a reusable cationic 2, 2[prime or minute]-bipyridyl palladium(II)/CuI system in water
    • Chen S, Wu W, Tsai F. Homocoupling reaction of terminal alkynes catalyzed by a reusable cationic 2, 2[prime or minute]-bipyridyl palladium(II)/CuI system in water. Green Chem, 2009, 11: 269-274
    • (2009) Green Chem , vol.11 , pp. 269-274
    • Chen, S.1    Wu, W.2    Tsai, F.3
  • 15
    • 33846358874 scopus 로고    scopus 로고
    • Cyclopalladated ferrocenylimines: Efficient catalysts for homocoupling and sonogashira reaction of terminal alkynes
    • Yang F, Cui X, Li Y, Zhang J, Ren G, Wu Y. Cyclopalladated ferrocenylimines: Efficient catalysts for homocoupling and sonogashira reaction of terminal alkynes. Tetrahedron, 2007, 63: 1963-1969
    • (2007) Tetrahedron , vol.63 , pp. 1963-1969
    • Yang, F.1    Cui, X.2    Li, Y.3    Zhang, J.4    Ren, G.5    Wu, Y.6
  • 16
    • 0037043192 scopus 로고    scopus 로고
    • Biphasic oxidation of arenes with oxygen catalyzed by a Pd(II)-heteropoly acid system: Oxidative coupling versus hydroxylation
    • Burton H, Kozhevnikov I. Biphasic oxidation of arenes with oxygen catalyzed by a Pd(II)-heteropoly acid system: Oxidative coupling versus hydroxylation. J Mol Catal A: Chem, 2002, 185: 285-290
    • (2002) J Mol Catal A: Chem , vol.185 , pp. 285-290
    • Burton, H.1    Kozhevnikov, I.2
  • 17
    • 77149179388 scopus 로고    scopus 로고
    • An efficient approach to homocoupling of terminal alkynes: Solvent-free synthesis of 1, 3-diynes using catalytic Cu(II) and base
    • Wang D, Li J, Li N, Gao T, Hou S, Chen B. An efficient approach to homocoupling of terminal alkynes: Solvent-free synthesis of 1, 3-diynes using catalytic Cu(II) and base. Green Chem, 2010, 12: 45-48
    • (2010) Green Chem , vol.12 , pp. 45-48
    • Wang, D.1    Li, J.2    Li, N.3    Gao, T.4    Hou, S.5    Chen, B.6
  • 18
    • 0022439743 scopus 로고
    • Selective coupling of dimethyl phthalate with palladium catalysts at atmospheric pressure
    • Shiotani A, Itatani H, Inagaki T. Selective coupling of dimethyl phthalate with palladium catalysts at atmospheric pressure. J Mol Catal, 1986, 34: 57-66
    • (1986) J Mol Catal , vol.34 , pp. 57-66
    • Shiotani, A.1    Itatani, H.2    Inagaki, T.3
  • 19
    • 33746712581 scopus 로고
    • Palladium-catalyzed syntheses of aromatic coupling compounds
    • Itatani H, Yoshimoto H. Palladium-catalyzed syntheses of aromatic coupling compounds. J Org Chem, 1973, 38: 76-79
    • (1973) J Org Chem , vol.38 , pp. 76-79
    • Itatani, H.1    Yoshimoto, H.2
  • 20
    • 4644345422 scopus 로고
    • Palladium-catalyzed competitive reaction of aromatic compounds
    • Yoshimoto H, Itatani H. Palladium-catalyzed competitive reaction of aromatic compounds. J Catal, 1973, 31: 8-12
    • (1973) J Catal , vol.31 , pp. 8-12
    • Yoshimoto, H.1    Itatani, H.2
  • 21
    • 0000368021 scopus 로고
    • Palladium-catalyzed coupling reaction of aromatic compounds
    • Yoshimoto H, Itatani H. Palladium-catalyzed coupling reaction of aromatic compounds. Bul. Chem Soc Jpn, 1973, 46: 2490-2492
    • (1973) Bul. Chem Soc Jpn , vol.46 , pp. 2490-2492
    • Yoshimoto, H.1    Itatani, H.2
  • 22
    • 0007317684 scopus 로고
    • Facile oxidative coupling of benzene by the palladium(II) acetate-dialkyl sulfide system
    • Fuchita Y, Taga M, Kawakami M, Kawachi F. Facile oxidative coupling of benzene by the palladium(II) acetate-dialkyl sulfide system. Bull Chem Soc Jpn, 1993, 66: 1294-1296
    • (1993) Bull Chem Soc Jpn , vol.66 , pp. 1294-1296
    • Fuchita, Y.1    Taga, M.2    Kawakami, M.3    Kawachi, F.4
  • 23
    • 0035532098 scopus 로고    scopus 로고
    • A selective synthesis of biphenyl by the Pd(OAc)2/MoO2(acac)2/O2/AcOH catalyst system
    • Okamoto M, Yamaji T. A selective synthesis of biphenyl by the Pd(OAc)2/MoO2(acac)2/O2/AcOH catalyst system. Chem Lett, 2001: 212-213
    • (2001) Chem Lett , pp. 212-213
    • Okamoto, M.1    Yamaji, T.2
  • 24
    • 0037433243 scopus 로고    scopus 로고
    • Direct coupling of benzene with olefin catalyzed by Pd(OAc)2 combined with heteropolyoxometalate under dioxygen
    • Yokota T, Tani M, Sakaguchi S, Ishii Y. Direct coupling of benzene with olefin catalyzed by Pd(OAc)2 combined with heteropolyoxometalate under dioxygen. J Am Chem Soc, 2003, 125: 1476-1477
    • (2003) J Am Chem Soc , vol.125 , pp. 1476-1477
    • Yokota, T.1    Tani, M.2    Sakaguchi, S.3    Ishii, Y.4
  • 25
    • 73449085833 scopus 로고    scopus 로고
    • Palladium-catalyzed regioselective oxidative coupling of indoles and one-pot synthesis of acetoxylated biindolyls
    • Liang Z, Zhao J, Zhang Y. Palladium-catalyzed regioselective oxidative coupling of indoles and one-pot synthesis of acetoxylated biindolyls. J Org Chem, 2010, 75: 170-177
    • (2010) J Org Chem , vol.75 , pp. 170-177
    • Liang, Z.1    Zhao, J.2    Zhang, Y.3
  • 26
    • 38849126856 scopus 로고    scopus 로고
    • Multiple C-H activations to construct biologically active molecules in a process completely free of organohalogen and organometallic components
    • Li B, Tian S, Fang Z, Shi Z. Multiple C-H activations to construct biologically active molecules in a process completely free of organohalogen and organometallic components. Angew Chem Int Ed, 2008, 47: 1115-1118
    • (2008) Angew Chem Int Ed , vol.47 , pp. 1115-1118
    • Li, B.1    Tian, S.2    Fang, Z.3    Shi, Z.4
  • 27
    • 47749112915 scopus 로고    scopus 로고
    • Palladium-catalyzed oxidative carbonylation of alkyl and aryl indium reagents with CO under mild conditions
    • Zhao Y, Jin L, Li P, Lei A. Palladium-catalyzed oxidative carbonylation of alkyl and aryl indium reagents with CO under mild conditions. J Am Chem Soc, 2008, 130: 9429-9433
    • (2008) J Am Chem Soc , vol.130 , pp. 9429-9433
    • Zhao, Y.1    Jin, L.2    Li, P.3    Lei, A.4
  • 28
    • 77951672796 scopus 로고    scopus 로고
    • Palladium-catalyzed aerobic oxidative carbonylation of arylboronate esters under mild conditions
    • Liu Q, Li G, He J, Liu J, Li P, Lei A. Palladium-catalyzed aerobic oxidative carbonylation of arylboronate esters under mild conditions. Angew Chem Int Ed, 2010, 49: 3371-3374
    • (2010) Angew Chem Int Ed , vol.49 , pp. 3371-3374
    • Liu, Q.1    Li, G.2    He, J.3    Liu, J.4    Li, P.5    Lei, A.6
  • 29
    • 79951604797 scopus 로고    scopus 로고
    • Pd-catalyzed direct and selective C-H functionalization: C3-acetoxylation of indoles
    • Liu Q, Li G, Yi H, Wu P, Liu J, Lei A. Pd-catalyzed direct and selective C-H functionalization: C3-acetoxylation of indoles. Chem Eur J., 2011, 17: 2353-2357
    • (2011) Chem Eur J. , vol.17 , pp. 2353-2357
    • Liu, Q.1    Li, G.2    Yi, H.3    Wu, P.4    Liu, J.5    Lei, A.6
  • 30
    • 80051779973 scopus 로고    scopus 로고
    • Palladium-catalyzed regioselective aerobic oxidative C-H/N-H carbonylation of heteroarenes under base-free conditions
    • Zhang H, Liu D, Chen CY, Liu C, Lei AW. Palladium-catalyzed regioselective aerobic oxidative C-H/N-H carbonylation of heteroarenes under base-free conditions. Chem-Eur J, 2011, 17: 9581-9585
    • (2011) Chem-Eur J , vol.17 , pp. 9581-9585
    • Zhang, H.1    Liu, D.2    Chen, C.Y.3    Liu, C.4    Lei, A.W.5
  • 31
    • 0035693812 scopus 로고    scopus 로고
    • Palladiumcatalyzed synthesis of biaryls from arylzinc compounds using n-chlorosuccinimide or oxygen as an oxidant
    • Hossain KM, Kameyama T, Shibata T, Takagi K. Palladiumcatalyzed synthesis of biaryls from arylzinc compounds using n-chlorosuccinimide or oxygen as an oxidant. Bull Chem Soc Jpn, 2001, 74: 2415-2420
    • (2001) Bull Chem Soc Jpn , vol.74 , pp. 2415-2420
    • Hossain, K.M.1    Kameyama, T.2    Shibata, T.3    Takagi, K.4
  • 35
    • 0000481305 scopus 로고
    • A reaction of palladium chloride with allyl alcohol
    • Smidt J, Hafner W. A reaction of palladium chloride with allyl alcohol. Angew Chem, 1959, 71: 284
    • (1959) Angew Chem , vol.71 , pp. 284
    • Smidt, J.1    Hafner, W.2
  • 36
    • 0037368965 scopus 로고    scopus 로고
    • The wacker reaction and related alkene oxidation reactions
    • Takacs JM, Jiang X. The wacker reaction and related alkene oxidation reactions. Curr Org Chem, 2003, 7: 369-396
    • (2003) Curr Org Chem , vol.7 , pp. 369-396
    • Takacs, J.M.1    Jiang, X.2
  • 37
    • 33645532122 scopus 로고    scopus 로고
    • Ligand-modulated palladium-catalyzed aerobic alcohol oxidations
    • Sigman MS, Jensen DR. Ligand-modulated palladium-catalyzed aerobic alcohol oxidations. Acc Chem Res, 2006, 39: 221-229
    • (2006) Acc Chem Res , vol.39 , pp. 221-229
    • Sigman, M.S.1    Jensen, D.R.2
  • 38
    • 33750166737 scopus 로고    scopus 로고
    • Mechanistic questions about the reaction of molecular oxygen with palladium in oxidase catalysis
    • Gligorich KM, Sigman MS. Mechanistic questions about the reaction of molecular oxygen with palladium in oxidase catalysis. Angew Chem Int Ed, 2006, 45: 6612-6615
    • (2006) Angew Chem Int Ed , vol.45 , pp. 6612-6615
    • Gligorich, K.M.1    Sigman, M.S.2
  • 39
    • 4143153074 scopus 로고    scopus 로고
    • Palladium oxidase catalysis. Selective oxidation of organic chemicals by direct dioxygen-coupled turnover
    • Stahl SS. Palladium oxidase catalysis. Selective oxidation of organic chemicals by direct dioxygen-coupled turnover. Angew Chem Int Ed, 2004, 43: 3400-3420
    • (2004) Angew Chem Int Ed , vol.43 , pp. 3400-3420
    • Stahl, S.S.1
  • 40
    • 67650602181 scopus 로고    scopus 로고
    • Recent advancements and challenges of palladiumII-catalyzed oxidation reactions with molecular oxygen as the sole oxidant
    • Gligorich KM, Sigman MS. Recent advancements and challenges of palladiumII-catalyzed oxidation reactions with molecular oxygen as the sole oxidant. Chem Commun, 2009: 3854-3867
    • (2009) Chem Commun , pp. 3854-3867
    • Gligorich, K.M.1    Sigman, M.S.2
  • 41
    • 4744343636 scopus 로고    scopus 로고
    • The renaissance of palladium(II)-catalyzed oxidation chemistry
    • Sigman MS, Schultz MJ. The renaissance of palladium(II)-catalyzed oxidation chemistry. Org Biomol Chem, 2004, 2: 2551-2554
    • (2004) Org Biomol Chem , vol.2 , pp. 2551-2554
    • Sigman, M.S.1    Schultz, M.J.2
  • 42
    • 80052802032 scopus 로고    scopus 로고
    • Synthesis of cyclic enones via direct palladiumcatalyzed aerobic dehydrogenation of ketones
    • Diao T, Stahl SS. Synthesis of cyclic enones via direct palladiumcatalyzed aerobic dehydrogenation of ketones. J Am Chem Soc, 2011, 133: 14566-14569
    • (2011) J Am Chem Soc , vol.133 , pp. 14566-14569
    • Diao, T.1    Stahl, S.S.2
  • 43
    • 1042276609 scopus 로고    scopus 로고
    • A sulfoxide-promoted, catalytic method for the regioselective synthesis of allylic acetates from monosubstituted olefins via C-H oxidation
    • Chen MS, White MC. A sulfoxide-promoted, catalytic method for the regioselective synthesis of allylic acetates from monosubstituted olefins via C-H oxidation. J Am Chem Soc, 2004, 126: 1346-1347
    • (2004) J Am Chem Soc , vol.126 , pp. 1346-1347
    • Chen, M.S.1    White, M.C.2
  • 44
    • 33644645936 scopus 로고    scopus 로고
    • Unexpected roles of molecular sieves in palladium-catalyzed aerobic alcohol oxidation
    • Steinhoff BA, King AE, Stahl SS. Unexpected roles of molecular sieves in palladium-catalyzed aerobic alcohol oxidation. J Org Chem, 2006, 71: 1861-1868
    • (2006) J Org Chem , vol.71 , pp. 1861-1868
    • Steinhoff, B.A.1    King, A.E.2    Stahl, S.S.3
  • 45
    • 34249028505 scopus 로고    scopus 로고
    • Two-faced reactivity of alkenes: Cis-versus trans-aminopalladation in aerobic Pd-catalyzed intramolecular aza-wacker reactions
    • Liu G, Stahl SS. Two-faced reactivity of alkenes: Cis-versus trans-aminopalladation in aerobic Pd-catalyzed intramolecular aza-wacker reactions. J Am Chem Soc, 2007, 129: 6328-6335
    • (2007) J Am Chem Soc , vol.129 , pp. 6328-6335
    • Liu, G.1    Stahl, S.S.2
  • 46
    • 0037028556 scopus 로고    scopus 로고
    • Mechanistic study of alcohol oxidation by the Pd(OAc)2/O2/DMSO catalyst system and implications for the development of improved aerobic oxidation catalysts
    • Steinhoff BA, Fix SR, Stahl SS. Mechanistic study of alcohol oxidation by the Pd(OAc)2/O2/DMSO catalyst system and implications for the development of improved aerobic oxidation catalysts. J Am Chem Soc, 2002, 124: 766-767
    • (2002) J Am Chem Soc , vol.124 , pp. 766-767
    • Steinhoff, B.A.1    Fix, S.R.2    Stahl, S.S.3
  • 47
    • 33645467565 scopus 로고    scopus 로고
    • Mechanism of Pd(OAc)2 /DMSO-catalyzed aerobic alcohol oxidation: Mass-transfer-limitation effects and catalyst decomposition pathways
    • Steinhoff BA, Stahl SS. Mechanism of Pd(OAc)2 /DMSO-catalyzed aerobic alcohol oxidation: Mass-transfer-limitation effects and catalyst decomposition pathways. J Am Chem Soc, 2006, 128: 4348-4355
    • (2006) J Am Chem Soc , vol.128 , pp. 4348-4355
    • Steinhoff, B.A.1    Stahl, S.S.2
  • 48
    • 30444437460 scopus 로고    scopus 로고
    • Convenient and efficient Pd-catalyzed regioselective oxyfunctionalization of terminal olefins by using molecular oxygen as sole reoxidant
    • Mitsudome T, Umetani T, Nosaka N, Mori K, Mizugaki T, Ebitani K, Kaneda K. Convenient and efficient Pd-catalyzed regioselective oxyfunctionalization of terminal olefins by using molecular oxygen as sole reoxidant. Angew Chem Int Ed, 2006, 45: 481-485
    • (2006) Angew Chem Int Ed , vol.45 , pp. 481-485
    • Mitsudome, T.1    Umetani, T.2    Nosaka, N.3    Mori, K.4    Mizugaki, T.5    Ebitani, K.6    Kaneda, K.7
  • 49
    • 0012253713 scopus 로고    scopus 로고
    • Ligand-modulated palladium oxidation catalysis: Mechanistic insights into aerobic alcohol oxidation with the Pd(OAc)2/pyridine catalyst system
    • Steinhoff BA, Stahl SS. Ligand-modulated palladium oxidation catalysis: Mechanistic insights into aerobic alcohol oxidation with the Pd(OAc)2/pyridine catalyst system. Org Lett, 2002, 4: 4179-4181
    • (2002) Org Lett , vol.4 , pp. 4179-4181
    • Steinhoff, B.A.1    Stahl, S.S.2
  • 50
    • 20444502894 scopus 로고    scopus 로고
    • Using mechanistic and computational studies to explain ligand effects in the palladium-catalyzed aerobic oxidation of alcohols
    • Schultz MJ, Adler RS, Zierkiewicz W, Privalov T, Sigman MS. Using mechanistic and computational studies to explain ligand effects in the palladium-catalyzed aerobic oxidation of alcohols. J Am Chem Soc, 2005, 127: 8499-8507
    • (2005) J Am Chem Soc , vol.127 , pp. 8499-8507
    • Schultz, M.J.1    Adler, R.S.2    Zierkiewicz, W.3    Privalov, T.4    Sigman, M.S.5
  • 51
    • 78650392932 scopus 로고    scopus 로고
    • Aerobic oxidative coupling of o-xylene: Discovery of 2-fluoropyridine as a ligand to support selective pdcatalyzed C-H functionalization
    • Izawa Y, Stahl SS. Aerobic oxidative coupling of o-xylene: Discovery of 2-fluoropyridine as a ligand to support selective pdcatalyzed C-H functionalization. Adv Synth Catal, 2010, 352: 3223-3229
    • (2010) Adv Synth Catal , vol.352 , pp. 3223-3229
    • Izawa, Y.1    Stahl, S.S.2
  • 52
    • 79960078229 scopus 로고    scopus 로고
    • Palladium-catalyzed aerobic dehydrogenation of substituted cyclohexanones to phenols
    • Izawa Y, Pun D, Stahl SS. Palladium-catalyzed aerobic dehydrogenation of substituted cyclohexanones to phenols. Science, 2011, 333: 209-213
    • (2011) Science , vol.333 , pp. 209-213
    • Izawa, Y.1    Pun, D.2    Stahl, S.S.3
  • 53
    • 4544248275 scopus 로고    scopus 로고
    • 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
    • Steinhoff BA, Guzei IA, Stahl SS. 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. J Am Chem Soc, 2004, 126: 11268-11278
    • (2004) J Am Chem Soc , vol.126 , pp. 11268-11278
    • Steinhoff, B.A.1    Guzei, I.A.2    Stahl, S.S.3
  • 54
    • 62349094304 scopus 로고    scopus 로고
    • Mechanism of Pd(OAc)2/pyridine catalyst reoxidation by O2: Influence of labile monodentate ligands and identification of a biomimetic mechanism for O2 activation
    • Popp BV, Stahl SS. Mechanism of Pd(OAc)2/pyridine catalyst reoxidation by O2: Influence of labile monodentate ligands and identification of a biomimetic mechanism for O2 activation. Chem-Eur J, 2009, 15: 2915-2922
    • (2009) Chem-Eur J , vol.15 , pp. 2915-2922
    • Popp, B.V.1    Stahl, S.S.2
  • 55
    • 2542558084 scopus 로고    scopus 로고
    • Homogeneous palladium catalyst suppressing pd black formation in air oxidation of alcohols
    • Iwasawa T, Tokunaga M, Obora Y, Tsuji Y. Homogeneous palladium catalyst suppressing pd black formation in air oxidation of alcohols. J Am Chem Soc, 2004, 126: 6554-6555
    • (2004) J Am Chem Soc , vol.126 , pp. 6554-6555
    • Iwasawa, T.1    Tokunaga, M.2    Obora, Y.3    Tsuji, Y.4
  • 56
    • 67849133067 scopus 로고    scopus 로고
    • Mechanism for activation of molecular oxygen by cis-and trans-(pyridine)2Pd(OAc)H: Pd0 versus direct insertion
    • Keith JM, Goddard WA. Mechanism for activation of molecular oxygen by cis-and trans-(pyridine)2Pd(OAc)H: Pd0 versus direct insertion. J Am Chem Soc, 2009, 131: 1416-1425
    • (2009) J Am Chem Soc , vol.131 , pp. 1416-1425
    • Keith, J.M.1    Goddard, W.A.2
  • 57
    • 29344454909 scopus 로고    scopus 로고
    • Bronsted base-modulated regioselectivity in the aerobic oxidative amination of styrene catalyzed by palladium
    • Timokhin VI, Stahl SS. Bronsted base-modulated regioselectivity in the aerobic oxidative amination of styrene catalyzed by palladium. J Am Chem Soc, 2005, 127: 17888-17893
    • (2005) J Am Chem Soc , vol.127 , pp. 17888-17893
    • Timokhin, V.I.1    Stahl, S.S.2
  • 58
    • 0034828614 scopus 로고    scopus 로고
    • Oxygenation of nitrogen-coordinated palladium(0): Synthetic, structural, and mechanistic studies and implications for aerobic oxidation catalysis
    • Stahl SS, Thorman JL, Nelson RC, Kozee MA. Oxygenation of nitrogen-coordinated palladium(0): Synthetic, structural, and mechanistic studies and implications for aerobic oxidation catalysis. J Am Chem Soc, 2001, 123: 7188-7189
    • (2001) J Am Chem Soc , vol.123 , pp. 7188-7189
    • Stahl, S.S.1    Thorman, J.L.2    Nelson, R.C.3    Kozee, M.A.4
  • 59
    • 33644945950 scopus 로고    scopus 로고
    • Oxidatively induced" reductive elimination of dioxygen from an ETA2-peroxopalladium(II) complex promoted by electron-deficient alkenes
    • Popp BV, Stahl SS. "Oxidatively induced" reductive elimination of dioxygen from an ETA2-peroxopalladium(II) complex promoted by electron-deficient alkenes. J Am Chem Soc, 2006, 128: 2804-2805
    • (2006) J Am Chem Soc , vol.128 , pp. 2804-2805
    • Popp, B.V.1    Stahl, S.S.2
  • 60
    • 0038276962 scopus 로고    scopus 로고
    • Mechanistic investigations of the palladium-catalyzed aerobic oxidative kinetic resolution of secondary alcohols using (-)-sparteine
    • Mueller JA, Sigman MS. Mechanistic investigations of the palladium-catalyzed aerobic oxidative kinetic resolution of secondary alcohols using (-)-sparteine. J Am Chem Soc, 2003, 125: 7005-7013
    • (2003) J Am Chem Soc , vol.125 , pp. 7005-7013
    • Mueller, J.A.1    Sigman, M.S.2
  • 61
    • 0037125518 scopus 로고    scopus 로고
    • Dual role of (-)-sparteine in the palladium-catalyzed aerobic oxidative kinetic resolution of secondary alcohols
    • Mueller JA, Jensen DR, Sigman MS. Dual role of (-)-sparteine in the palladium-catalyzed aerobic oxidative kinetic resolution of secondary alcohols. J Am Chem Soc, 2002, 124: 8202-8203
    • (2002) J Am Chem Soc , vol.124 , pp. 8202-8203
    • Mueller, J.A.1    Jensen, D.R.2    Sigman, M.S.3
  • 62
    • 77956084669 scopus 로고    scopus 로고
    • Experimental and computational study of a direct O2-coupled wacker oxidation: Water dependence in the absence of Cu salts
    • Anderson BJ, Keith JA, Sigman MS. Experimental and computational study of a direct O2-coupled wacker oxidation: Water dependence in the absence of Cu salts. J Am Chem Soc, 2010, 132: 11872-11874
    • (2010) J Am Chem Soc , vol.132 , pp. 11872-11874
    • Anderson, B.J.1    Keith, J.A.2    Sigman, M.S.3
  • 63
    • 25444454085 scopus 로고    scopus 로고
    • Pd-mediated activation of molecular oxygen in a nonpolar medium
    • Keith JM, Nielsen RJ, Oxgaard J, Goddard WA. Pd-mediated activation of molecular oxygen in a nonpolar medium. J Am Chem Soc, 2005, 127: 13172-13179
    • (2005) J Am Chem Soc , vol.127 , pp. 13172-13179
    • Keith, J.M.1    Nielsen, R.J.2    Oxgaard, J.3    Goddard, W.A.4
  • 64
    • 36448968256 scopus 로고    scopus 로고
    • Palladium-catalyzed reductive coupling of styrenes and organostannanes under aerobic conditions
    • Gligorich KM, Cummings SA, Sigman MS. Palladium-catalyzed reductive coupling of styrenes and organostannanes under aerobic conditions. J Am Chem Soc, 2007, 129: 14193-14195
    • (2007) J Am Chem Soc , vol.129 , pp. 14193-14195
    • Gligorich, K.M.1    Cummings, S.A.2    Sigman, M.S.3
  • 65
    • 80052078778 scopus 로고    scopus 로고
    • Reaction of O2 with [(-)-sparteine]Pd(H)Cl: Evidence for an intramolecular [H-L]+ "reductive elimination" pathway
    • Decharin N, Popp BV, Stahl SS. Reaction of O2 with [(-)-sparteine]Pd(H) Cl: Evidence for an intramolecular [H-L]+ "reductive elimination" pathway. J Am Chem Soc, 2011, 133: 13268-13271
    • (2011) J Am Chem Soc , vol.133 , pp. 13268-13271
    • Decharin, N.1    Popp, B.V.2    Stahl, S.S.3
  • 66
    • 70350678840 scopus 로고    scopus 로고
    • Insertion of molecular oxygen into a palladium(II) methyl bond: A radical chain mechanism involving palladium(III) intermediates
    • Boisvert L, Denney MC, Kloek HS, Goldberg KI. Insertion of molecular oxygen into a palladium(II) methyl bond: A radical chain mechanism involving palladium(III) intermediates. J Am Chem Soc, 2009, 131: 15802-15814
    • (2009) J Am Chem Soc , vol.131 , pp. 15802-15814
    • Boisvert, L.1    Denney, M.C.2    Kloek, H.S.3    Goldberg, K.I.4
  • 67
    • 0042865830 scopus 로고    scopus 로고
    • A well-defined complex for palladium-catalyzed aerobic oxidation of alcohols: Design, synthesis and mechanistic considerations
    • Jensen DR, Schultz MJ, Mueller JA, Sigman MS. A well-defined complex for palladium-catalyzed aerobic oxidation of alcohols: Design, synthesis and mechanistic considerations. Angew Chem Int Ed, 2003, 42: 3810-3813
    • (2003) Angew Chem Int Ed , vol.42 , pp. 3810-3813
    • Jensen, D.R.1    Schultz, M.J.2    Mueller, J.A.3    Sigman, M.S.4
  • 68
    • 4143086010 scopus 로고    scopus 로고
    • Characterization of peroxo and hydroperoxo intermediates in the aerobic oxidation of n-heterocycliccarbene-coordinated palladium(0)
    • Konnick MM, Guzei IA, Stahl SS. Characterization of peroxo and hydroperoxo intermediates in the aerobic oxidation of n-heterocycliccarbene- coordinated palladium(0). J Am Chem Soc, 2004, 126: 10212-10213
    • (2004) J Am Chem Soc , vol.126 , pp. 10212-10213
    • Konnick, M.M.1    Guzei, I.A.2    Stahl, S.S.3
  • 69
    • 33745688109 scopus 로고    scopus 로고
    • Reaction of molecular oxygen with a PdII-hydride to produce a Pd(II)-hydroperoxide: Acid catalysis and implications for Pd-catalyzed aerobic oxidation reactions
    • Konnick MM, Gandhi BA, Guzei IA, Stahl SS. Reaction of molecular oxygen with a PdII-hydride to produce a Pd(II)-hydroperoxide: Acid catalysis and implications for Pd-catalyzed aerobic oxidation reactions. Angew Chem Int Ed, 2006, 45: 2904-2907
    • (2006) Angew Chem Int Ed , vol.45 , pp. 2904-2907
    • Konnick, M.M.1    Gandhi, B.A.2    Guzei, I.A.3    Stahl, S.S.4
  • 70
    • 33846551900 scopus 로고    scopus 로고
    • Reaction of molecular oxygen with an nhc-coordinated Pd0 complex: Computational insights and experimental implications
    • Popp BV, Wendlandt JE, Landis CR, Stahl SS. Reaction of molecular oxygen with an nhc-coordinated Pd0 complex: Computational insights and experimental implications. Angew Chem Int Ed, 2007, 46: 601-604
    • (2007) Angew Chem Int Ed , vol.46 , pp. 601-604
    • Popp, B.V.1    Wendlandt, J.E.2    Landis, C.R.3    Stahl, S.S.4
  • 71
    • 34247125694 scopus 로고    scopus 로고
    • Insertion of molecular oxygen into a palladium-hydride bond: Computational evidence for two nearly isoenergetic pathways
    • Popp BV, Stahl SS. Insertion of molecular oxygen into a palladium-hydride bond: Computational evidence for two nearly isoenergetic pathways. J Am Chem Soc, 2007, 129: 4410-4422
    • (2007) J Am Chem Soc , vol.129 , pp. 4410-4422
    • Popp, B.V.1    Stahl, S.S.2
  • 72
    • 42649133825 scopus 로고    scopus 로고
    • Reaction of molecular oxygen with a pdii-hydride to produce a Pd(II)-hydroperoxide: Experimental evidence for an hx-reductive-elimination pathway
    • Konnick MM, Stahl SS. Reaction of molecular oxygen with a pdii-hydride to produce a Pd(II)-hydroperoxide: Experimental evidence for an hx-reductive-elimination pathway. J Am Chem Soc, 2008, 130: 5753-5762
    • (2008) J Am Chem Soc , vol.130 , pp. 5753-5762
    • Konnick, M.M.1    Stahl, S.S.2
  • 73
    • 79954481454 scopus 로고    scopus 로고
    • O2 insertion into a palladium(II)-hydride bond: Observation of mechanistic crossover between HX-reductive-elimination and hydrogen-atom- abstraction pathways
    • Konnick MM, Decharin N, Popp BV, Stahl SS. O2 insertion into a palladium(II)-hydride bond: Observation of mechanistic crossover between HX-reductive-elimination and hydrogen-atom-abstraction pathways. Chem Sci, 2011, 2: 326-330
    • (2011) Chem Sci , vol.2 , pp. 326-330
    • Konnick, M.M.1    Decharin, N.2    Popp, B.V.3    Stahl, S.S.4
  • 76
    • 84961981202 scopus 로고    scopus 로고
    • Mechanism of the palladium-catalyzed homocoupling of arylboronic acids: Key involvement of a palladium peroxo complex
    • Adamo C, Amatore C, Ciofini I, Jutand A, Lakmini H. Mechanism of the palladium-catalyzed homocoupling of arylboronic acids: Key involvement of a palladium peroxo complex. J Am Chem Soc, 2006, 128: 6829-6836
    • (2006) J Am Chem Soc , vol.128 , pp. 6829-6836
    • Adamo, C.1    Amatore, C.2    Ciofini, I.3    Jutand, A.4    Lakmini, H.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.