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Volumn 554, Issue 7690, 2018, Pages 86-91

Generating carbyne equivalents with photoredox catalysis

Author keywords

[No Author keywords available]

Indexed keywords

BARBAN; DULOXETINE; FINGOLIMOD; IMATINIB; PACLITAXEL;

EID: 85041480415     PISSN: 00280836     EISSN: 14764687     Source Type: Journal    
DOI: 10.1038/nature25185     Document Type: Article
Times cited : (147)

References (31)
  • 2
    • 33947337530 scopus 로고
    • Formation and reactions of monovalent carbon intermediates I. Photolysis of diethyl mercuribisdiazoacetate
    • Thap, D. M., Gunning, H. E. & Strausz, O. P. Formation and reactions of monovalent carbon intermediates. I. Photolysis of diethyl mercuribisdiazoacetate. J. Am. Chem. Soc. 89, 6785-6787 (1967).
    • (1967) J. Am. Chem. Soc. , vol.89 , pp. 6785-6787
    • Thap, D.M.1    Gunning, H.E.2    Strausz, O.P.3
  • 3
    • 33947319672 scopus 로고
    • Formation and reactions of monovalent carbon intermediates II. Further studies on the decomposition of diethyl mercurybisdiazoacetate
    • Strausz, O. P., Thap, D. M. & Font, J. Formation and reactions of monovalent carbon intermediates. II. Further studies on the decomposition of diethyl mercurybisdiazoacetate. J. Am. Chem. Soc. 90, 1930-1931 (1968).
    • (1968) J. Am. Chem. Soc. , vol.90 , pp. 1930-1931
    • Strausz, O.P.1    Thap, D.M.2    Font, J.3
  • 4
    • 0344883108 scopus 로고
    • Formation and reactions of monovalent carbon intermediates III. Reaction of carbethoxymethyne with olefins
    • Strausz, O. P. et al. Formation and reactions of monovalent carbon intermediates. III. Reaction of carbethoxymethyne with olefins. J. Am. Chem. Soc. 96, 5723-5732 (1974).
    • (1974) J. Am. Chem. Soc. , vol.96 , pp. 5723-5732
    • Strausz, O.P.1
  • 5
    • 33847800434 scopus 로고
    • Photolysis of diethyl mercurybisdiazoacetate and ethyl diazoacetate in chloroalkanes
    • Patrick, T. B. & Kovitch, G. H. Photolysis of diethyl mercurybisdiazoacetate and ethyl diazoacetate in chloroalkanes. J. Org. Chem. 40, 1527-1528 (1975).
    • (1975) J. Org. Chem. , vol.40 , pp. 1527-1528
    • Patrick, T.B.1    Kovitch, G.H.2
  • 6
    • 33947092186 scopus 로고
    • Photodecomposition of diethyl mercurybis (diazoacetate) in several heterocyclic systems
    • Patrick, T. B. & Wu, T.-T. Photodecomposition of diethyl mercurybis (diazoacetate) in several heterocyclic systems. J. Org. Chem. 43, 1506-1509 (1978).
    • (1978) J. Org. Chem. , vol.43 , pp. 1506-1509
    • Patrick, T.B.1    Wu, T.-T.2
  • 7
    • 84874639402 scopus 로고    scopus 로고
    • Alkyne metathesis on the rise
    • Fürstner, A. Alkyne metathesis on the rise. Angew. Chem. Int. Ed. 52, 2794-2819 (2013).
    • (2013) Angew. Chem. Int. Ed. , vol.52 , pp. 2794-2819
    • Fürstner, A.1
  • 8
    • 17644401663 scopus 로고    scopus 로고
    • Formation of a carbon-carbon triple bond by coupling reactions in aqueous solution
    • Bino, A., Ardon, M. & Shirman, E. Formation of a carbon-carbon triple bond by coupling reactions in aqueous solution. Science 308, 234-235 (2005).
    • (2005) Science , vol.308 , pp. 234-235
    • Bino, A.1    Ardon, M.2    Shirman, E.3
  • 9
    • 84855283261 scopus 로고    scopus 로고
    • Do carbyne radicals really exist in aqueous solution? Angew
    • Bogoslavsky, B. et al. Do carbyne radicals really exist in aqueous solution? Angew. Chem. Int. Ed. 51, 90-94 (2012).
    • (2012) Chem. Int. Ed. , vol.51 , pp. 90-94
    • Bogoslavsky, B.1
  • 10
    • 84956959993 scopus 로고    scopus 로고
    • The medicinal chemist's toolbox for late stage functionalization of drug-like molecules
    • Cernak, T., Dykstra, K. D., Tyagarajan, S., Vachal, P. & Krska, S. W. The medicinal chemist's toolbox for late stage functionalization of drug-like molecules. Chem. Soc. Rev. 45, 546-576 (2016).
    • (2016) Chem. Soc. Rev. , vol.45 , pp. 546-576
    • Cernak, T.1    Dykstra, K.D.2    Tyagarajan, S.3    Vachal, P.4    Krska, S.W.5
  • 11
    • 0001636127 scopus 로고
    • Considerations regarding interstellar molecules
    • Swings, P. & Rosenfeld, L. Considerations regarding interstellar molecules. Astrophys. J. 86, 483-486 (1937).
    • (1937) Astrophys. J. , vol.86 , pp. 483-486
    • Swings, P.1    Rosenfeld, L.2
  • 12
    • 33846593003 scopus 로고
    • Radio detection of interstellar CH
    • Rydbeck, O. E. H., Ellder, J. & Irvine, W. M. Radio detection of interstellar CH. Nature 246, 466-468 (1973).
    • (1973) Nature , vol.246 , pp. 466-468
    • Rydbeck, O.E.H.1    Ellder, J.2    Irvine, W.M.3
  • 13
    • 84991235788 scopus 로고    scopus 로고
    • Herschel/HIFI spectral mapping of C+, CH+, and CH in Orion BN/KL: The prevailing role of ultraviolet irradiation in CH+ formation
    • Morris, P. W. et al. Herschel/HIFI spectral mapping of C+, CH+, and CH in Orion BN/KL: the prevailing role of ultraviolet irradiation in CH+ formation. Astrophys. J. 829, 15-46 (2016).
    • (2016) Astrophys. J. , vol.829 , pp. 15-46
    • Morris, P.W.1
  • 15
    • 84942279542 scopus 로고    scopus 로고
    • Modern organic synthesis with diazocarbonyl compounds
    • Ford, A. et al. Modern organic synthesis with diazocarbonyl compounds. Chem. Rev. 115, 9981-10080 (2015).
    • (2015) Chem. Rev. , vol.115 , pp. 9981-10080
    • Ford, A.1
  • 16
    • 53349122064 scopus 로고    scopus 로고
    • Merging photoredox catalysis with organocatalysis: The direct asymmetric alkylation of aldehydes
    • Nicewicz, D. A. & MacMillan, D. W. C. Merging photoredox catalysis with organocatalysis: the direct asymmetric alkylation of aldehydes. Science 322, 77-80 (2008).
    • (2008) Science , vol.322 , pp. 77-80
    • Nicewicz, D.A.1    MacMillan, D.W.C.2
  • 17
    • 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
  • 18
    • 84960405249 scopus 로고    scopus 로고
    • Advances in synthetic applications of hypervalent iodine compounds
    • Yoshimura, A. & Zhdankin, V. V. Advances in synthetic applications of hypervalent iodine compounds. Chem. Rev. 116, 3328-3435 (2016).
    • (2016) Chem. Rev. , vol.116 , pp. 3328-3435
    • Yoshimura, A.1    Zhdankin, V.V.2
  • 19
    • 84964577582 scopus 로고    scopus 로고
    • Synthetic applications of hypervalent iodine (III) reagents enabled by visible light photoredox catalysis
    • Wang, L. & Liu, J. Synthetic applications of hypervalent iodine (III) reagents enabled by visible light photoredox catalysis. Eur. J. Org. Chem. 2016, 1813-1824 (2016).
    • (2016) Eur. J. Org. Chem. 2016, 1813-1824
    • Wang, L.1    Liu, J.2
  • 20
    • 33748237071 scopus 로고
    • Aryliodonio diazo compounds: SN reactions at the C atom as a novel reaction type for diazo compounds
    • Weiss, R., Seubert, J. & Hampel, F. Aryliodonio diazo compounds: SN reactions at the C atom as a novel reaction type for diazo compounds. Angew. Chem. Int. Ed. Engl. 33, 1952-1953 (1994).
    • (1994) Angew. Chem. Int. Ed. Engl. , vol.33 , pp. 1952-1953
    • Weiss, R.1    Seubert, J.2    Hampel, F.3
  • 21
    • 84881221863 scopus 로고    scopus 로고
    • Nucleophilic halogenations of diazo compounds, a complementary principle for the synthesis of halodiazo compounds: Experimental and theoretical Studies
    • Schnaars, C., Hennum, M. & Bonge-Hansen, T. Nucleophilic halogenations of diazo compounds, a complementary principle for the synthesis of halodiazo compounds: experimental and theoretical Studies. J. Org. Chem. 78, 7488-7497 (2013).
    • (2013) J. Org. Chem. , vol.78 , pp. 7488-7497
    • Schnaars, C.1    Hennum, M.2    Bonge-Hansen, T.3
  • 22
    • 84979224081 scopus 로고    scopus 로고
    • Charge-transferdirected radical substitution enables para-selective C-H functionalization
    • Boursalian, G. B., Ham, W. S., Mazzotti, A. R. & Ritter, T. Charge-transferdirected radical substitution enables para-selective C-H functionalization. Nat. Chem. 8, 810-815 (2016).
    • (2016) Nat. Chem. , vol.8 , pp. 810-815
    • Boursalian, G.B.1    Ham, W.S.2    Mazzotti, A.R.3    Ritter, T.4
  • 23
    • 84926442923 scopus 로고    scopus 로고
    • Palladium-catalyzed C-H functionalization of acyldiazomethane and tandem cross-coupling reactions
    • Ye, F. et al. Palladium-catalyzed C-H functionalization of acyldiazomethane and tandem cross-coupling reactions. J. Am. Chem. Soc. 137, 4435-4444 (2015).
    • (2015) J. Am. Chem. Soc. , vol.137 , pp. 4435-4444
    • Ye, F.1
  • 24
    • 85013669644 scopus 로고    scopus 로고
    • Synthesis of 2, 2, 2,-trichloroethyl aryl-and vinyldiazoacetates by palladium-catalyzed cross-coupling
    • Fu, L., Mighion, J. D., Voight, E. A. & Davies, H. M. L. Synthesis of 2, 2, 2,-trichloroethyl aryl-and vinyldiazoacetates by palladium-catalyzed cross-coupling. Chem. Eur. J. 23, 3272-3275 (2017).
    • (2017) Chem. Eur. J. , vol.23 , pp. 3272-3275
    • Fu, L.1    Mighion, J.D.2    Voight, E.A.3    Davies, H.M.L.4
  • 25
    • 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
  • 26
    • 84887566303 scopus 로고    scopus 로고
    • Profound methyl effects in drug discovery and a call for new C-H methylation reactions
    • Schönherr, H. & Cernak, T. Profound methyl effects in drug discovery and a call for new C-H methylation reactions. Angew. Chem. Int. Ed. 52, 12256-12267 (2013).
    • (2013) Angew. Chem. Int. Ed. , vol.52 , pp. 12256-12267
    • Schönherr, H.1    Cernak, T.2
  • 27
    • 85022215653 scopus 로고    scopus 로고
    • Selective sp3 C-H alkylation via polarity-match-based cross-coupling
    • Le, C., Liang, Y., Evans, R. W., Li, X. & Macmillan, D. W. C. Selective sp3 C-H alkylation via polarity-match-based cross-coupling. Nature 547, 79-83 (2017).
    • (2017) Nature , vol.547 , pp. 79-83
    • Le, C.1    Liang, Y.2    Evans, R.W.3    Li, X.4    Macmillan, D.W.C.5
  • 28
    • 79956011526 scopus 로고    scopus 로고
    • Silver-catalyzed C? C bond formation between methane and ethyldiazoacetate in supercritical CO2
    • Caballero, A. et al. Silver-catalyzed C? C bond formation between methane and ethyldiazoacetate in supercritical CO2. Science 332, 835-838 (2011).
    • (2011) Science , vol.332 , pp. 835-838
    • Caballero, A.1
  • 29
    • 84939856467 scopus 로고    scopus 로고
    • Rh (II)-catalyzed reactions of diazoesters with organozinc reagents
    • Panish, R., Selvaraj, R. & Fox, J. M. Rh (II)-catalyzed reactions of diazoesters with organozinc reagents. Org. Lett. 17, 3978-3981 (2015).
    • (2015) Org. Lett. , vol.17 , pp. 3978-3981
    • Panish, R.1    Selvaraj, R.2    Fox, J.M.3
  • 30
    • 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
  • 31
    • 0033620447 scopus 로고    scopus 로고
    • Reversible interconversion between singlet and triplet 2-naphthyl (carbomethoxy)carbene
    • Zhu, Z., Bally, T., Stracener, L. & McMahon, R. J. Reversible interconversion between singlet and triplet 2-naphthyl (carbomethoxy)carbene. J. Am. Chem. Soc. 121, 2863-2874 (1999).
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 2863-2874
    • Zhu, Z.1    Bally, T.2    Stracener, L.3    McMahon, R.J.4


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