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Volumn 49, Issue 7, 2016, Pages 1429-1439

Single-Electron Transmetalation via Photoredox/Nickel Dual Catalysis: Unlocking a New Paradigm for sp3-sp2 Cross-Coupling

Author keywords

[No Author keywords available]

Indexed keywords

BORIC ACID; NICKEL; ORGANOMETALLIC COMPOUND; THIOL DERIVATIVE;

EID: 84979555810     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/acs.accounts.6b00214     Document Type: Article
Times cited : (577)

References (46)
  • 1
    • 84929190819 scopus 로고    scopus 로고
    • Recent Developments in the Suzuki-Miyaura Reaction: 2010-2014
    • Maluenda, I.; Navarro, O. Recent Developments in the Suzuki-Miyaura Reaction: 2010-2014 Molecules 2015, 20, 7528-7557 10.3390/molecules20057528
    • (2015) Molecules , vol.20 , pp. 7528-7557
    • Maluenda, I.1    Navarro, O.2
  • 2
    • 2042507954 scopus 로고
    • Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds
    • Miyaura, N.; Suzuki, A. Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds Chem. Rev. 1995, 95, 2457-2483 10.1021/cr00039a007
    • (1995) Chem. Rev. , vol.95 , pp. 2457-2483
    • Miyaura, N.1    Suzuki, A.2
  • 3
    • 84897735057 scopus 로고    scopus 로고
    • Palladium-Catalysed Direct Cross-Coupling of Secondary Alkyllithium Reagents
    • Vila, C.; Giannerini, M.; Hornillos, V.; Fañanás-Mastral, M.; Feringa, B. L. Palladium-Catalysed Direct Cross-Coupling of Secondary Alkyllithium Reagents Chem. Sci. 2014, 5, 1361-1367 10.1039/c3sc53047g
    • (2014) Chem. Sci. , vol.5 , pp. 1361-1367
    • Vila, C.1    Giannerini, M.2    Hornillos, V.3    Fañanás-Mastral, M.4    Feringa, B.L.5
  • 4
    • 0000259867 scopus 로고
    • Nickel-Phosphine Complex-Catalyzed Grignard Coupling. I. Cross-Coupling of Alkyl, Aryl, and Alkenyl Grignard Reagents with Aryl and Alkenyl Halides: General Scope and Limitations
    • Tamao, K.; Sumitani, K.; Kiso, Y.; Zembayashi, M.; Fujioka, A.; Kodama, S.; Nakajima, I.; Minato, A.; Kumada, M. Nickel-Phosphine Complex-Catalyzed Grignard Coupling. I. Cross-Coupling of Alkyl, Aryl, and Alkenyl Grignard Reagents with Aryl and Alkenyl Halides: General Scope and Limitations Bull. Chem. Soc. Jpn. 1976, 49, 1958-1969 10.1246/bcsj.49.1958
    • (1976) Bull. Chem. Soc. Jpn. , vol.49 , pp. 1958-1969
    • Tamao, K.1    Sumitani, K.2    Kiso, Y.3    Zembayashi, M.4    Fujioka, A.5    Kodama, S.6    Nakajima, I.7    Minato, A.8    Kumada, M.9
  • 5
    • 67650566611 scopus 로고    scopus 로고
    • Negishi Coupling of Secondary Alkylzinc Halides with Aryl Bromides and Chlorides
    • Han, C.; Buchwald, S. L. Negishi Coupling of Secondary Alkylzinc Halides with Aryl Bromides and Chlorides J. Am. Chem. Soc. 2009, 131, 7532-7533 10.1021/ja902046m
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 7532-7533
    • Han, C.1    Buchwald, S.L.2
  • 6
    • 84879338745 scopus 로고    scopus 로고
    • Stereoretentive Pd-Catalysed Stille Cross-Coupling Reactions of Secondary Alkyl Azastannatranes and Aryl Halides
    • Li, L.; Wang, C.; Huang, R.; Biscoe, M. R. Stereoretentive Pd-Catalysed Stille Cross-Coupling Reactions of Secondary Alkyl Azastannatranes and Aryl Halides Nat. Chem. 2013, 5, 607-612 10.1038/nchem.1652
    • (2013) Nat. Chem. , vol.5 , pp. 607-612
    • Li, L.1    Wang, C.2    Huang, R.3    Biscoe, M.R.4
  • 8
    • 0034600318 scopus 로고    scopus 로고
    • Versatile Catalysts for the Suzuki Cross-Coupling of Arylboronic Acids with Aryl and Vinyl Halides and Triflates under Mild Conditions
    • Littke, A. F.; Dai, C.; Fu, G. C. Versatile Catalysts for the Suzuki Cross-Coupling of Arylboronic Acids with Aryl and Vinyl Halides and Triflates Under Mild Conditions J. Am. Chem. Soc. 2000, 122, 4020-4028 10.1021/ja0002058
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 4020-4028
    • Littke, A.F.1    Dai, C.2    Fu, G.C.3
  • 10
    • 47749142142 scopus 로고    scopus 로고
    • Efficient Cross-Coupling of Secondary Alkyltrifluoroborates with Aryl Chlorides - Reaction Discovery Using Parallel Microscale Experimentation
    • Dreher, S. D.; Dormer, P. G.; Sandrock, D. L.; Molander, G. A. Efficient Cross-Coupling of Secondary Alkyltrifluoroborates with Aryl Chlorides-Reaction Discovery Using Parallel Microscale Experimentation J. Am. Chem. Soc. 2008, 130, 9257-9259 10.1021/ja8031423
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 9257-9259
    • Dreher, S.D.1    Dormer, P.G.2    Sandrock, D.L.3    Molander, G.A.4
  • 11
    • 84907943523 scopus 로고    scopus 로고
    • Stereospecific Pd-Catalyzed Cross-Coupling Reactions of Secondary Alkylboron Nucleophiles and Aryl Chlorides
    • Li, L.; Zhao, S.; Joshi-Pangu, A.; Diane, M.; Biscoe, M. R. Stereospecific Pd-Catalyzed Cross-Coupling Reactions of Secondary Alkylboron Nucleophiles and Aryl Chlorides J. Am. Chem. Soc. 2014, 136, 14027-14030 10.1021/ja508815w
    • (2014) J. Am. Chem. Soc. , vol.136 , pp. 14027-14030
    • Li, L.1    Zhao, S.2    Joshi-Pangu, A.3    Diane, M.4    Biscoe, M.R.5
  • 12
    • 78650163175 scopus 로고    scopus 로고
    • Stereospecific Cross-Coupling of Secondary Alkyl β-Trifluoroboratoamides
    • Sandrock, D. L.; Jean-Gerard, L.; Chen, C.; Dreher, S. D.; Molander, G. A. Stereospecific Cross-Coupling of Secondary Alkyl β-Trifluoroboratoamides J. Am. Chem. Soc. 2010, 132, 17108-17110 10.1021/ja108949w
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 17108-17110
    • Sandrock, D.L.1    Jean-Gerard, L.2    Chen, C.3    Dreher, S.D.4    Molander, G.A.5
  • 13
    • 67749113467 scopus 로고    scopus 로고
    • Cross-Coupling Reactions of Chiral Secondary Organoboronic Esters with Retention of Configuration
    • Imao, D.; Glasspoole, B. W.; Laberge, V. S.; Crudden, C. M. Cross-Coupling Reactions of Chiral Secondary Organoboronic Esters with Retention of Configuration J. Am. Chem. Soc. 2009, 131, 5024-5025 10.1021/ja8094075
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 5024-5025
    • Imao, D.1    Glasspoole, B.W.2    Laberge, V.S.3    Crudden, C.M.4
  • 14
    • 0001277585 scopus 로고
    • Alkyl Group Isomerization in the Cross-Coupling Reaction of Secondary Alkyl Grignard Reagents with Organic Halides in the Presence of Nickel-Phosphine Complexes as Catalysts
    • Tamao, K.; Kiso, Y.; Sumitani, J.; Kumada, M. Alkyl Group Isomerization in the Cross-Coupling Reaction of Secondary Alkyl Grignard Reagents with Organic Halides in the Presence of Nickel-Phosphine Complexes as Catalysts J. Am. Chem. Soc. 1972, 94, 9268-9269 10.1021/ja00781a070
    • (1972) J. Am. Chem. Soc. , vol.94 , pp. 9268-9269
    • Tamao, K.1    Kiso, Y.2    Sumitani, J.3    Kumada, M.4
  • 15
    • 0020826828 scopus 로고
    • Mechanism of the Palladium-Catalyzed Couplings of Acid Chlorides with Organostannanes
    • Labadie, J. W.; Stille, J. K. Mechanism of the Palladium-Catalyzed Couplings of Acid Chlorides with Organostannanes J. Am. Chem. Soc. 1983, 105, 6129-6137 10.1021/ja00357a026
    • (1983) J. Am. Chem. Soc. , vol.105 , pp. 6129-6137
    • Labadie, J.W.1    Stille, J.K.2
  • 17
    • 79953179740 scopus 로고    scopus 로고
    • Direct Alkylation of Heteroaryls using Potassium Alkyl- and Alkoxymethyltrifluoroborates
    • Molander, G. A.; Colombel, V.; Braz, V. Direct Alkylation of Heteroaryls using Potassium Alkyl- and Alkoxymethyltrifluoroborates Org. Lett. 2011, 13, 1852-1855 10.1021/ol2003572
    • (2011) Org. Lett. , vol.13 , pp. 1852-1855
    • Molander, G.A.1    Colombel, V.2    Braz, V.3
  • 18
    • 84900544451 scopus 로고    scopus 로고
    • Recent Advances in Homogeneous Nickel Catalysis
    • Tasker, S. Z.; Standley, E. A.; Jamison, T. F. Recent Advances in Homogeneous Nickel Catalysis Nature 2014, 509, 299-309 10.1038/nature13274
    • (2014) Nature , vol.509 , pp. 299-309
    • Tasker, S.Z.1    Standley, E.A.2    Jamison, T.F.3
  • 19
    • 84979578174 scopus 로고    scopus 로고
    • Dual Catalysis Strategies in Photochemical Synthesis
    • Skubi, K. L.; Blum, T. R.; Yoon, T. P. Dual Catalysis Strategies in Photochemical Synthesis Chem. Rev. 2016, 10.1021/acs.chemrev.6b00018
    • (2016) Chem. Rev.
    • Skubi, K.L.1    Blum, T.R.2    Yoon, T.P.3
  • 20
    • 84880124916 scopus 로고    scopus 로고
    • Visible Light Photoredox Catalysis with Transition Metal Complexes: Applications in Organic Synthesis
    • Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Visible Light Photoredox Catalysis with Transition Metal Complexes: Applications in Organic Synthesis Chem. Rev. 2013, 113, 5322-5363 10.1021/cr300503r
    • (2013) Chem. Rev. , vol.113 , pp. 5322-5363
    • Prier, C.K.1    Rankic, D.A.2    MacMillan, D.W.C.3
  • 21
    • 84896707663 scopus 로고    scopus 로고
    • Solar Synthesis: Prospects in Visible Light Photocatalysis
    • Schultz, D. M.; Yoon, T. P. Solar Synthesis: Prospects in Visible Light Photocatalysis Science 2014, 343, 1239176 10.1126/science.1239176
    • (2014) Science , vol.343 , pp. 1239176
    • Schultz, D.M.1    Yoon, T.P.2
  • 22
    • 84871071736 scopus 로고    scopus 로고
    • Visible Light-Induced Selective Generation of Radicals from Organoborates by Photoredox Catalysis
    • Yasu, Y.; Koike, T.; Akita, M. Visible Light-Induced Selective Generation of Radicals from Organoborates by Photoredox Catalysis Adv. Synth. Catal. 2012, 354, 3414-3420 10.1002/adsc.201200588
    • (2012) Adv. Synth. Catal. , vol.354 , pp. 3414-3420
    • Yasu, Y.1    Koike, T.2    Akita, M.3
  • 23
    • 0030218425 scopus 로고    scopus 로고
    • Nickel-Catalyzed Electrochemical Homocoupling of Alkenyl Halides: Rates and Mechanisms
    • Cannes, C.; Labbé, E.; Durandetti, M.; Devaud, M.; Nédélec, J. Y. Nickel-Catalyzed Electrochemical Homocoupling of Alkenyl Halides: Rates and Mechanisms J. Electroanal. Chem. 1996, 412, 85-93 10.1016/0022-0728(96)04605-0
    • (1996) J. Electroanal. Chem. , vol.412 , pp. 85-93
    • Cannes, C.1    Labbé, E.2    Durandetti, M.3    Devaud, M.4    Nédélec, J.Y.5
  • 24
    • 84904800842 scopus 로고    scopus 로고
    • Single-electron Transmetalation in Organoboron Cross-coupling by Photoredox/Nickel Dual Catalysis
    • Tellis, J. C.; Primer, D. N.; Molander, G. A. Single-electron Transmetalation in Organoboron Cross-coupling by Photoredox/Nickel Dual Catalysis Science 2014, 345, 433-436 10.1126/science.1253647
    • (2014) Science , vol.345 , pp. 433-436
    • Tellis, J.C.1    Primer, D.N.2    Molander, G.A.3
  • 25
    • 0035825767 scopus 로고    scopus 로고
    • Cross-Coupling Reactions of Potassium Alkyltrifluoroborates with Aryl and 1-Alkenyl Trifluoromethanesulfonates
    • Molander, G. A.; Ito, T. Cross-Coupling Reactions of Potassium Alkyltrifluoroborates with Aryl and 1-Alkenyl Trifluoromethanesulfonates Org. Lett. 2001, 3, 393-396 10.1021/ol006896u
    • (2001) Org. Lett. , vol.3 , pp. 393-396
    • Molander, G.A.1    Ito, T.2
  • 26
    • 84923260920 scopus 로고    scopus 로고
    • Single-Electron Transmetalation: An Enabling Technology for Secondary Alkylboron Cross-Coupling
    • Primer, D. N.; Karakaya, I.; Tellis, J. C.; Molander, G. A. Single-Electron Transmetalation: An Enabling Technology for Secondary Alkylboron Cross-Coupling J. Am. Chem. Soc. 2015, 137, 2195-2198 10.1021/ja512946e
    • (2015) J. Am. Chem. Soc. , vol.137 , pp. 2195-2198
    • Primer, D.N.1    Karakaya, I.2    Tellis, J.C.3    Molander, G.A.4
  • 27
    • 84955181954 scopus 로고    scopus 로고
    • α-Arylation/Heteroarylation of Chiral α-Aminomethyltrifluoroborates by Synergistic Iridium Photoredox/Nickel Cross-Coupling Catalysis
    • El Khatib, M.; Serafim, R. A. M.; Molander, G. A. α-Arylation/Heteroarylation of Chiral α-Aminomethyltrifluoroborates by Synergistic Iridium Photoredox/Nickel Cross-Coupling Catalysis Angew. Chem., Int. Ed. 2016, 55, 254-258 10.1002/anie.201506147
    • (2016) Angew. Chem., Int. Ed. , vol.55 , pp. 254-258
    • El Khatib, M.1    Serafim, R.A.M.2    Molander, G.A.3
  • 28
    • 84935125121 scopus 로고    scopus 로고
    • Photoredox Cross-Coupling: Ir/Ni Dual Catalysis for the Synthesis of Benzylic Ethers
    • Karakaya, I.; Primer, D. N.; Molander, G. A. Photoredox Cross-Coupling: Ir/Ni Dual Catalysis for the Synthesis of Benzylic Ethers Org. Lett. 2015, 17, 3294-3297 10.1021/acs.orglett.5b01463
    • (2015) Org. Lett. , vol.17 , pp. 3294-3297
    • Karakaya, I.1    Primer, D.N.2    Molander, G.A.3
  • 29
    • 84954383075 scopus 로고    scopus 로고
    • Single-Electron Transmetalation: Synthesis of 1,1-Diaryl-2,2,2-trifluoroethanes by Photoredox/Nickel Dual Catalytic Cross-Coupling
    • Ryu, D.; Primer, D. N.; Tellis, J. C.; Molander, G. A. Single-Electron Transmetalation: Synthesis of 1,1-Diaryl-2,2,2-trifluoroethanes by Photoredox/Nickel Dual Catalytic Cross-Coupling Chem.-Eur. J. 2016, 22, 120-123 10.1002/chem.201504079
    • (2016) Chem. - Eur. J. , vol.22 , pp. 120-123
    • Ryu, D.1    Primer, D.N.2    Tellis, J.C.3    Molander, G.A.4
  • 31
    • 84942885483 scopus 로고    scopus 로고
    • Protecting Group-free, Selective Cross-coupling of Alkyltrifluoroborates with Borylated Aryl Bromides via Photoredox/Nickel Dual Catalysis
    • Yamashita, Y.; Tellis, J. C.; Molander, G. A. Protecting Group-free, Selective Cross-coupling of Alkyltrifluoroborates with Borylated Aryl Bromides via Photoredox/Nickel Dual Catalysis Proc. Natl. Acad. Sci. U. S. A. 2015, 112, 12026-12029 10.1073/pnas.1509715112
    • (2015) Proc. Natl. Acad. Sci. U. S. A. , vol.112 , pp. 12026-12029
    • Yamashita, Y.1    Tellis, J.C.2    Molander, G.A.3
  • 32
    • 84928492420 scopus 로고    scopus 로고
    • Nickel-Catalyzed Cross-Coupling of Photoredox-Generated Radicals: Uncovering a General Manifold for Stereoconvergence in Nickel-Catalyzed Cross-Couplings
    • Gutierrez, O.; Tellis, J. C.; Primer, D. N.; Molander, G. A.; Kozlowski, M. C. Nickel-Catalyzed Cross-Coupling of Photoredox-Generated Radicals: Uncovering a General Manifold for Stereoconvergence in Nickel-Catalyzed Cross-Couplings J. Am. Chem. Soc. 2015, 137, 4896-4899 10.1021/ja513079r
    • (2015) J. Am. Chem. Soc. , vol.137 , pp. 4896-4899
    • Gutierrez, O.1    Tellis, J.C.2    Primer, D.N.3    Molander, G.A.4    Kozlowski, M.C.5
  • 34
    • 84897508311 scopus 로고    scopus 로고
    • Photosubstitution of Dicyanoarenes by Hypervalent Allylsilicon Reagents via Photoinduced Electron Transfer
    • Matsuoka, D.; Nishigaichi, Y. Photosubstitution of Dicyanoarenes by Hypervalent Allylsilicon Reagents via Photoinduced Electron Transfer Chem. Lett. 2014, 43, 559-561 10.1246/cl.131132
    • (2014) Chem. Lett. , vol.43 , pp. 559-561
    • Matsuoka, D.1    Nishigaichi, Y.2
  • 35
    • 0000821098 scopus 로고
    • 1 Salts of Bis(o-arylenedioxy)organosiliconic Acids
    • 1 Salts of Bis(o-arylenedioxy)organosiliconic Acids J. Am. Chem. Soc. 1964, 86, 3170-3171 10.1021/ja01069a054
    • (1964) J. Am. Chem. Soc. , vol.86 , pp. 3170-3171
    • Frye, C.L.1
  • 36
    • 1242307375 scopus 로고    scopus 로고
    • Preparation and Palladium-Catalyzed Cross-Coupling of Aryl Triethylammonium Bis(catechol) Silicates with Aryl Triflates
    • Seganish, W. M.; DeShong, P. Preparation and Palladium-Catalyzed Cross-Coupling of Aryl Triethylammonium Bis(catechol) Silicates with Aryl Triflates J. Org. Chem. 2004, 69, 1137-1143 10.1021/jo035309q
    • (2004) J. Org. Chem. , vol.69 , pp. 1137-1143
    • Seganish, W.M.1    DeShong, P.2
  • 37
    • 0003547629 scopus 로고
    • Pentacoordinate Organosilicon Compounds in Organic Synthesis: Cross-coupling of Alkenylsiliconates with Organic Halides and Triflates Catalyzed by Palladium Complex
    • Hosomi, A.; Kohra, S.; Tominaga, Y. Pentacoordinate Organosilicon Compounds in Organic Synthesis: Cross-coupling of Alkenylsiliconates with Organic Halides and Triflates Catalyzed by Palladium Complex Chem. Pharm. Bull. 1988, 36, 4622-4625 10.1248/cpb.36.4622
    • (1988) Chem. Pharm. Bull. , vol.36 , pp. 4622-4625
    • Hosomi, A.1    Kohra, S.2    Tominaga, Y.3
  • 38
    • 84955312797 scopus 로고    scopus 로고
    • Base-Free Photoredox/Nickel Dual-Catalytic Cross-Coupling of Ammonium Alkylsilicates
    • Jouffroy, M.; Primer, D. N.; Molander, G. A. Base-Free Photoredox/Nickel Dual-Catalytic Cross-Coupling of Ammonium Alkylsilicates J. Am. Chem. Soc. 2016, 138, 475-478 10.1021/jacs.5b10963
    • (2016) J. Am. Chem. Soc. , vol.138 , pp. 475-478
    • Jouffroy, M.1    Primer, D.N.2    Molander, G.A.3
  • 39
    • 84962439086 scopus 로고    scopus 로고
    • Primary Alkyl Bis-catecholato Silicates in Dual Photoredox/Nickel Catalysis: Aryl- and Heteroaryl-alkyl Cross coupling Reactions
    • The groups of Fensterbank and Goddard corroborated this finding recently, see
    • The groups of Fensterbank and Goddard corroborated this finding recently, see: Lévêque, C.; Chenneberg, L.; Corcé, V.; Goddard, J.-P.; Ollivier, C.; Fensterbank, L. Primary Alkyl Bis-catecholato Silicates in Dual Photoredox/Nickel Catalysis: Aryl- and Heteroaryl-alkyl Cross coupling Reactions Org. Chem. Front. 2016, 3, 462-465 10.1039/C6QO00014B
    • (2016) Org. Chem. Front. , vol.3 , pp. 462-465
    • Lévêque, C.1    Chenneberg, L.2    Corcé, V.3    Goddard, J.-P.4    Ollivier, C.5    Fensterbank, L.6
  • 40
    • 84943457879 scopus 로고    scopus 로고
    • Silicates as Latent Alkyl Radical Precursors: Visible-Light Photocatalytic Oxidation of Hypervalent Bis-Catecholato Silicon Compounds
    • Corcé, V.; Chamoreau, L.-M.; Derat, E.; Goddard, J.-P.; Ollivier, C.; Fensterbank, L. Silicates as Latent Alkyl Radical Precursors: Visible-Light Photocatalytic Oxidation of Hypervalent Bis-Catecholato Silicon Compounds Angew. Chem., Int. Ed. 2015, 54, 11414-11418 10.1002/anie.201504963
    • (2015) Angew. Chem., Int. Ed. , vol.54 , pp. 11414-11418
    • Corcé, V.1    Chamoreau, L.-M.2    Derat, E.3    Goddard, J.-P.4    Ollivier, C.5    Fensterbank, L.6
  • 41
    • 84906334075 scopus 로고    scopus 로고
    • Photoredox α-Vinylation of α-Amino Acids and N-Aryl Amines
    • Noble, A.; MacMillan, D. W. C. Photoredox α-Vinylation of α-Amino Acids and N-Aryl Amines J. Am. Chem. Soc. 2014, 136, 11602-11605 10.1021/ja506094d
    • (2014) J. Am. Chem. Soc. , vol.136 , pp. 11602-11605
    • Noble, A.1    MacMillan, D.W.C.2
  • 42
    • 84959018709 scopus 로고    scopus 로고
    • Engaging Alkenyl Halides with Alkylsilicates via Photoredox Dual Catalysis
    • Patel, N. R.; Kelly, C. B.; Jouffroy, M.; Molander, G. A. Engaging Alkenyl Halides with Alkylsilicates via Photoredox Dual Catalysis Org. Lett. 2016, 18, 764-767 10.1021/acs.orglett.6b00024
    • (2016) Org. Lett. , vol.18 , pp. 764-767
    • Patel, N.R.1    Kelly, C.B.2    Jouffroy, M.3    Molander, G.A.4
  • 44
    • 84963851481 scopus 로고    scopus 로고
    • Accessing Elaborated 2,1-Borazaronaphthalene Cores using Photoredox/Nickel Dual-Catalytic Functionalization
    • Jouffroy, M.; Davies, G. H. M; Molander, G. A. Accessing Elaborated 2,1-Borazaronaphthalene Cores using Photoredox/Nickel Dual-Catalytic Functionalization Org. Lett. 2016, 18, 1606-1609 10.1021/acs.orglett.6b00466
    • (2016) Org. Lett. , vol.18 , pp. 1606-1609
    • Jouffroy, M.1    Davies, G.H.M.2    Molander, G.A.3
  • 45
    • 84959132380 scopus 로고    scopus 로고
    • Thioetherification via Photoredox/Nickel Dual Catalysis
    • Jouffroy, M.; Kelly, C. B.; Molander, G. A. Thioetherification via Photoredox/Nickel Dual Catalysis Org. Lett. 2016, 18, 876-879 10.1021/acs.orglett.6b00208
    • (2016) Org. Lett. , vol.18 , pp. 876-879
    • Jouffroy, M.1    Kelly, C.B.2    Molander, G.A.3
  • 46
    • 0037393779 scopus 로고    scopus 로고
    • Bond Dissociation Energies of Organic Molecules
    • Blanksby, S. J.; Ellison, G. B. Bond Dissociation Energies of Organic Molecules Acc. Chem. Res. 2003, 36, 255-263 10.1021/ar020230d
    • (2003) Acc. Chem. Res. , vol.36 , pp. 255-263
    • Blanksby, S.J.1    Ellison, G.B.2


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