메뉴 건너뛰기




Volumn 536, Issue 7616, 2016, Pages 322-325

Metallaphotoredox-catalysed sp3-sp3 cross-coupling of carboxylic acids with alkyl halides

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; CARBOXYLIC ACID; ELECTROPHILE; HALIDE; METAL; NICKEL; NUCLEOPHILE; PALLADIUM; TIROFIBAN; TRANSITION ELEMENT; TYROSINE;

EID: 84982303783     PISSN: 00280836     EISSN: 14764687     Source Type: Journal    
DOI: 10.1038/nature19056     Document Type: Article
Times cited : (375)

References (30)
  • 2
    • 84896131010 scopus 로고    scopus 로고
    • Sp3-sp3 Coupling reactions in the synthesis of natural products and biologically active molecules
    • Geist, E., Kirschning, A., Schmidt, T. sp3-sp3 Coupling reactions in the synthesis of natural products and biologically active molecules. Natural Prod. Rep. 31, 441-448 (2014).
    • (2014) Natural Prod. Rep. , vol.31 , pp. 441-448
    • Geist, E.1    Kirschning, A.2    Schmidt, T.3
  • 3
    • 84960110771 scopus 로고    scopus 로고
    • Recent developments in Negishi cross-coupling reactions
    • Haas, D., Hammann, J. M., Greiner, R., Knochel, P. Recent developments in Negishi cross-coupling reactions. ACS Catal. 6, 1540-1552 (2016).
    • (2016) ACS Catal. , vol.6 , pp. 1540-1552
    • Haas, D.1    Hammann, J.M.2    Greiner, R.3    Knochel, P.4
  • 4
    • 69249123855 scopus 로고    scopus 로고
    • Nickel-catalysed Negishi cross-coupling reactions: Scope and mechanisms
    • Phapale, V. B., Cárdenas, D. J. Nickel-catalysed Negishi cross-coupling reactions: scope and mechanisms. Chem. Soc. Rev. 38, 1598-1607 (2009).
    • (2009) Chem. Soc. Rev. , vol.38 , pp. 1598-1607
    • Phapale, V.B.1    Cárdenas, D.J.2
  • 5
    • 79952656192 scopus 로고    scopus 로고
    • Advances in transition metal (Pd,Ni,Fe)-catalyzed cross-coupling reactions using alkyl-organometallics as reaction partners
    • Jana, R., Pathak, T. P., Sigman, M. S. Advances in transition metal (Pd,Ni,Fe)-catalyzed cross-coupling reactions using alkyl-organometallics as reaction partners. Chem. Rev. 111, 1417-1492 (2011).
    • (2011) Chem. Rev. , vol.111 , pp. 1417-1492
    • Jana, R.1    Pathak, T.P.2    Sigman, M.S.3
  • 6
    • 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 509, 299-309 (2014).
    • (2014) Nature , vol.509 , pp. 299-309
    • Tasker, S.Z.1    Standley, E.A.2    Jamison, T.F.3
  • 7
    • 84964558188 scopus 로고    scopus 로고
    • A general alkyl-alkyl cross-coupling enabled by redox-active esters and alkylzinc reagents
    • Qin, T. et al. A general alkyl-alkyl cross-coupling enabled by redox-active esters and alkylzinc reagents. Science 352, 801-805 (2016).
    • (2016) Science , vol.352 , pp. 801-805
    • Qin, T.1
  • 8
    • 0345404157 scopus 로고    scopus 로고
    • An efficient nickelcatalyzed cross-coupling between sp3 carbon centers
    • Giovannini, R., Stüdemann, T., Dussin, G., Knochel, P. An efficient nickelcatalyzed cross-coupling between sp3 carbon centers. Angew. Chem. Int. Ed. 37, 2387-2390 (1998).
    • (1998) Angew. Chem. Int. Ed. , vol.37 , pp. 2387-2390
    • Giovannini, R.1    Stüdemann, T.2    Dussin, G.3    Knochel, P.4
  • 9
    • 0344861888 scopus 로고    scopus 로고
    • Cross-couplings of unactivated secondary alkyl halides: Room-temperature nickel-catalyzed Negishi reactions of alkyl bromides and iodides
    • Zhou, J., Fu, G. C. Cross-couplings of unactivated secondary alkyl halides: room-temperature nickel-catalyzed Negishi reactions of alkyl bromides and iodides. J. Am. Chem. Soc. 125, 14726-14727 (2003).
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 14726-14727
    • Zhou, J.1    Fu, G.C.2
  • 10
    • 0037165715 scopus 로고    scopus 로고
    • Nickel-catalyzed cross-coupling reaction of Grignard reagents with alkyl halides and tosylates: Remarkable effect of 1,3-butadienes
    • Terao, J., Watanabe, H., Ikumi, A., Kuniyasu, H., Kambe, N. Nickel-catalyzed cross-coupling reaction of Grignard reagents with alkyl halides and tosylates: remarkable effect of 1,3-butadienes. J. Am. Chem. Soc. 124, 4222-4223 (2002).
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 4222-4223
    • Terao, J.1    Watanabe, H.2    Ikumi, A.3    Kuniyasu, H.4    Kambe, N.5
  • 11
    • 34547789922 scopus 로고    scopus 로고
    • Alkyl-alkyl Suzuki cross-couplings of unactivated secondary alkyl halides at room temperature
    • Saito, B., Fu, G. C. Alkyl-alkyl Suzuki cross-couplings of unactivated secondary alkyl halides at room temperature. J. Am. Chem. Soc. 129, 9602-9603 (2007).
    • (2007) J. Am. Chem. Soc. , vol.129 , pp. 9602-9603
    • Saito, B.1    Fu, G.C.2
  • 12
    • 71049126548 scopus 로고    scopus 로고
    • Escape from flatland: Increasing saturation as an approach to improving clinical success
    • Lovering, F., Bikker, J., Humblet, C. Escape from flatland: increasing saturation as an approach to improving clinical success. J. Med. Chem. 52, 6752-6756 (2009).
    • (2009) J. Med. Chem. , vol.52 , pp. 6752-6756
    • Lovering, F.1    Bikker, J.2    Humblet, C.3
  • 13
    • 78650383080 scopus 로고    scopus 로고
    • Visible light photoredox catalysis: Applications in organic synthesis
    • Narayanam, J. M. R., Stephenson, C. R. J. Visible light photoredox catalysis: applications in organic synthesis. Chem. Soc. Rev. 40, 102-113 (2011).
    • (2011) Chem. Soc. Rev. , vol.40 , pp. 102-113
    • Narayanam, J.M.R.1    Stephenson, C.R.J.2
  • 14
    • 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. 113, 5322-5363 (2013).
    • (2013) Chem. Rev. , vol.113 , pp. 5322-5363
    • Prier, C.K.1    Rankic, D.A.2    MacMillan, D.W.C.3
  • 15
    • 84942354069 scopus 로고    scopus 로고
    • O-H hydrogen bonding promotes H-atom transfer from C-H bonds for C-alkylation of alcohols
    • Jeffrey, J. L., Terrett, J. A., MacMillan, D. W. C. O-H hydrogen bonding promotes H-atom transfer from C-H bonds for C-alkylation of alcohols. Science 349, 1532-1536 (2015).
    • (2015) Science , vol.349 , pp. 1532-1536
    • Jeffrey, J.L.1    Terrett, J.A.2    MacMillan, D.W.C.3
  • 16
    • 84939839315 scopus 로고    scopus 로고
    • Switching on elusive organometallic mechanisms with photoredox catalysis
    • Terrett, J. A., Cuthbertson, J. D., Shurtleff, V. W., MacMillan, D. W. C. Switching on elusive organometallic mechanisms with photoredox catalysis. Nature 524, 330-334 (2015).
    • (2015) Nature , vol.524 , pp. 330-334
    • Terrett, J.A.1    Cuthbertson, J.D.2    Shurtleff, V.W.3    MacMillan, D.W.C.4
  • 17
    • 83055161587 scopus 로고    scopus 로고
    • Roomtemperature C-H arylation: Merger of Pd-catalyzed C-H functionalization and visible-light photocatalysis
    • Kalyani, D., McMurtrey, K. B., Neufeldt, S. R., Sanford, M. S. Roomtemperature C-H arylation: merger of Pd-catalyzed C-H functionalization and visible-light photocatalysis. J. Am. Chem. Soc. 133, 18566-18569 (2011).
    • (2011) J. Am. Chem. Soc. , vol.133 , pp. 18566-18569
    • Kalyani, D.1    McMurtrey, K.B.2    Neufeldt, S.R.3    Sanford, M.S.4
  • 18
    • 84876487932 scopus 로고    scopus 로고
    • Combining gold and photoredox catalysis: Visible light-mediated oxy-and aminoarylation of alkenes
    • Sahoo, B., Hopkinson, M. N., Glorius, F. Combining gold and photoredox catalysis: visible light-mediated oxy-and aminoarylation of alkenes. J. Am. Chem. Soc. 135, 5505-5508 (2013).
    • (2013) J. Am. Chem. Soc. , vol.135 , pp. 5505-5508
    • Sahoo, B.1    Hopkinson, M.N.2    Glorius, F.3
  • 19
    • 85027954273 scopus 로고    scopus 로고
    • Combining rhodium and photoredox catalysis for C-H functionalizations of arenes: Oxidative Heck reactions with visible light
    • Fabry, D. C., Zoller, J., Raja, S., Rueping, M. Combining rhodium and photoredox catalysis for C-H functionalizations of arenes: oxidative Heck reactions with visible light. Angew. Chem. Int. Ed. 53, 10228-10231 (2014).
    • (2014) Angew. Chem. Int. Ed. , vol.53 , pp. 10228-10231
    • Fabry, D.C.1    Zoller, J.2    Raja, S.3    Rueping, M.4
  • 20
    • 84904797499 scopus 로고    scopus 로고
    • Merging photoredox with nickel catalysis: Coupling of-carboxyl sp3-carbons with aryl halides
    • Zuo, Z. et al. Merging photoredox with nickel catalysis: coupling of-carboxyl sp3-carbons with aryl halides. Science 345, 437-440 (2014).
    • (2014) Science , vol.345 , pp. 437-440
    • Zuo, Z.1
  • 21
    • 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 345, 433-436 (2014).
    • (2014) Science , vol.345 , pp. 433-436
    • Tellis, J.C.1    Primer, D.N.2    Molander, G.A.3
  • 22
    • 84966292281 scopus 로고    scopus 로고
    • Decarboxylative cross-electrophile coupling of N-hydroxyphthalimide esters with aryl iodides
    • Huihui, K. M. M. et al. Decarboxylative cross-electrophile coupling of N-hydroxyphthalimide esters with aryl iodides. J. Am. Chem. Soc. 138, 5016-5019 (2016).
    • (2016) J. Am. Chem. Soc. , vol.138 , pp. 5016-5019
    • Huihui, K.M.M.1
  • 23
    • 28044466429 scopus 로고    scopus 로고
    • Single-layer electroluminescent devices and photoinduced hydrogen production from an ionic iridium(III) complex
    • Lowry, M. S. et al. Single-layer electroluminescent devices and photoinduced hydrogen production from an ionic iridium(III) complex. Chem. Mater. 17, 5712-5719 (2005).
    • (2005) Chem. Mater. , vol.17 , pp. 5712-5719
    • Lowry, M.S.1
  • 24
    • 2942684055 scopus 로고    scopus 로고
    • Investigation of the reductive coupling of aryl halides and/or ethyl chloroacetate electrocatalyzed by the precursor NiX2(bpy) with X = Cl, Br or MeSO3 and bpy = 2,2-dipyridyl
    • Durandetti, M., Devaud, M., Perichon, J. Investigation of the reductive coupling of aryl halides and/or ethyl chloroacetate electrocatalyzed by the precursor NiX2(bpy) with X = Cl, Br or MeSO3 and bpy = 2,2-dipyridyl. New J. Chem. 20, 659-667 (1996).
    • (1996) New J. Chem. , vol.20 , pp. 659-667
    • Durandetti, M.1    Devaud, M.2    Perichon, J.3
  • 25
    • 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. 137, 4896-4899 (2015).
    • (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
  • 26
    • 84962339561 scopus 로고    scopus 로고
    • Density Functional Theory Studies of Negishi Alkyl-alkyl Cross-coupling Reactions Catalyzed by A Methylterpyridyl-Ni(I) Complex
    • Lin, X., Phillips, D. L. Density functional theory studies of Negishi alkyl-alkyl cross-coupling reactions catalyzed by a methylterpyridyl-Ni(I) complex. J. Org. Chem. 73, 3680-3688 (2008).
    • (2008) J. Org. Chem. , vol.73 , pp. 3680-3688
    • Lin, X.1    Phillips, D.L.2
  • 27
    • 79955701623 scopus 로고    scopus 로고
    • A structure-activity study of Ni-catalyzed alkyl-alkyl Kumada coupling. Improved catalysts for coupling of secondary alkyl halides
    • Ren, P., Vechorkin, O., von Allmen, K., Scopelliti, R., Hu, X. A structure-activity study of Ni-catalyzed alkyl-alkyl Kumada coupling. Improved catalysts for coupling of secondary alkyl halides. J. Am. Chem. Soc. 133, 7084-7095 (2011).
    • (2011) J. Am. Chem. Soc. , vol.133 , pp. 7084-7095
    • Ren, P.1    Vechorkin, O.2    Von Allmen, K.3    Scopelliti, R.4    Hu, X.5
  • 28
    • 84913539477 scopus 로고    scopus 로고
    • Nickel-catalyzed Negishi arylations of propargylic bromides: A mechanistic investigation
    • Schley, N. D., Fu, G. C. Nickel-catalyzed Negishi arylations of propargylic bromides: a mechanistic investigation. J. Am. Chem. Soc. 136, 16588-16593 (2014).
    • (2014) J. Am. Chem. Soc. , vol.136 , pp. 16588-16593
    • Schley, N.D.1    Fu, G.C.2
  • 29
    • 79955419410 scopus 로고    scopus 로고
    • Synopsis of some recent tactical application of bioisosteres in drug design
    • Meanwell, N. A. Synopsis of some recent tactical application of bioisosteres in drug design. J. Med. Chem. 54, 2529-2591 (2011).
    • (2011) J. Med. Chem. , vol.54 , pp. 2529-2591
    • Meanwell, N.A.1
  • 30
    • 0027096411 scopus 로고
    • Non-peptide fibrinogen receptor antagonists. 1. Discovery and design of exosite inhibitors
    • Hartman, G. D. et al. Non-peptide fibrinogen receptor antagonists. 1. Discovery and design of exosite inhibitors. J. Med. Chem. 35, 4640-4642 (1992).
    • (1992) J. Med. Chem. , vol.35 , pp. 4640-4642
    • Hartman, G.D.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.