메뉴 건너뛰기




Volumn 7, Issue 9, 2015, Pages 712-717

A meta-selective C-H borylation directed by a secondary interaction between ligand and substrate

Author keywords

[No Author keywords available]

Indexed keywords


EID: 84939783555     PISSN: 17554330     EISSN: 17554349     Source Type: Journal    
DOI: 10.1038/nchem.2322     Document Type: Article
Times cited : (390)

References (30)
  • 1
    • 53949088904 scopus 로고    scopus 로고
    • Transition-metal-catalyzed carbon-carbon bond formation via carbon-hydrogen bond cleavage
    • Kakiuchi, F. & Kochi, T. Transition-metal-catalyzed carbon-carbon bond formation via carbon-hydrogen bond cleavage. Synthesis 3013-3039 (2008).
    • (2008) Synthesis , pp. 3013-3039
    • Kakiuchi, F.1    Kochi, T.2
  • 2
    • 67649488045 scopus 로고    scopus 로고
    • Palladium(II)-catalyzed C-H activation/C-C cross-coupling reactions: Versatility and practicality
    • Chen, X., Engle, K. M., Wang, D.-H. & Yu, J.-Q. Palladium(II)-catalyzed C-H activation/C-C cross-coupling reactions: versatility and practicality. Angew. Chem. Int. Ed. 48, 5094-5115 (2009).
    • (2009) Angew. Chem. Int. Ed , vol.48 , pp. 5094-5115
    • Chen, X.1    Engle, K.M.2    Wang, D.-H.3    Yu, J.-Q.4
  • 3
    • 77349090183 scopus 로고    scopus 로고
    • Rhodium-catalyzed C-C bond formation via heteroatom-directed C-H bond activation
    • Colby, D. A., Bergman, R. G. & Ellman, J. A. Rhodium-catalyzed C-C bond formation via heteroatom-directed C-H bond activation. Chem. Rev. 110, 624-655 (2010).
    • (2010) Chem. Rev , vol.110 , pp. 624-655
    • Colby, D.A.1    Bergman, R.G.2    Ellman, J.A.3
  • 4
    • 79952689970 scopus 로고    scopus 로고
    • Organic reactions catalyzed by rhenium carbonyl complexes
    • Kuninobu, Y. & Takai, K. Organic reactions catalyzed by rhenium carbonyl complexes. Chem. Rev. 111, 1938-1953 (2011).
    • (2011) Chem. Rev , vol.111 , pp. 1938-1953
    • Kuninobu, Y.1    Takai, K.2
  • 5
    • 84886793220 scopus 로고    scopus 로고
    • Catalytic functionalization of C(sp2)-H and C(sp3)-H bonds using bidentate directing groups
    • Rouquet, G. & Chatani, N. Catalytic functionalization of C(sp2)-H and C(sp3)-H bonds using bidentate directing groups. Angew. Chem. Int. Ed. 52, 11726-11743 (2013).
    • (2013) Angew. Chem. Int. Ed , vol.52 , pp. 11726-11743
    • Rouquet, G.1    Chatani, N.2
  • 6
    • 84900332865 scopus 로고    scopus 로고
    • Transition metal-catalyzed direct nucleophilic addition of C-H bonds to carbon-heteroatom double bonds
    • Zhang, X.-S., Chen, K. & Shi, Z.-J. Transition metal-catalyzed direct nucleophilic addition of C-H bonds to carbon-heteroatom double bonds. Chem. Sci. 5, 2146-2159 (2014).
    • (2014) Chem. Sci , vol.5 , pp. 2146-2159
    • Zhang, X.-S.1    Chen, K.2    Shi, Z.-J.3
  • 7
    • 84869436026 scopus 로고    scopus 로고
    • Directed functionalization of C-H bonds: Now also meta selective
    • Truong, T. & Daugulis, O. Directed functionalization of C-H bonds: now also meta selective. Angew. Chem. Int. Ed. 51, 11677-11679 (2012).
    • (2012) Angew. Chem. Int. Ed , vol.51 , pp. 11677-11679
    • Truong, T.1    Daugulis, O.2
  • 8
    • 0037059546 scopus 로고    scopus 로고
    • Remarkably selective iridium catalysts for the elaboration of aromatic C-H bonds
    • Cho, J.-Y., Tse, M. K., Holmes, D., Maleczka, R. E. Jr & Smith, M. R. III. Remarkably selective iridium catalysts for the elaboration of aromatic C-H bonds. Science 295, 305-308 (2002).
    • (2002) Science , vol.295 , pp. 305-308
    • Cho, J.-Y.1    Tse, M.K.2    Holmes, D.3    Maleczka, R.E.4    Smith, M.R.5
  • 9
    • 0037160365 scopus 로고    scopus 로고
    • Mild iridium-catalyzed borylation of arenes. High turnover numbers, room temperature reactions, and isolation of a potential intermediate
    • Ishiyama, T. et al. Mild iridium-catalyzed borylation of arenes. High turnover numbers, room temperature reactions, and isolation of a potential intermediate. J. Am. Chem. Soc. 124, 390-391 (2002).
    • (2002) J. Am. Chem. Soc , vol.124 , pp. 390-391
    • Ishiyama, T.1
  • 10
    • 0037119304 scopus 로고    scopus 로고
    • A stoichiometric aromatic C-H borylation catalyzed by iridium(I)/2, 2'-bipyridine complexes at room temperature
    • Ishiyama, T., Takagi, J., Hartwig, J. F. & Miyaura, N. A stoichiometric aromatic C-H borylation catalyzed by iridium(I)/2, 2'-bipyridine complexes at room temperature. Angew. Chem. Int. Ed. 41, 3056-3058 (2002).
    • (2002) Angew. Chem. Int. Ed , vol.41 , pp. 3056-3058
    • Ishiyama, T.1    Takagi, J.2    Hartwig, J.F.3    Miyaura, N.4
  • 11
    • 37849049915 scopus 로고    scopus 로고
    • Meta halogenation of 1, 3-disubstituted arenes via iridium-catalyzed arene borylation
    • Murphy, J. M., Liao, X. & Hartwig, J. F. Meta halogenation of 1, 3-disubstituted arenes via iridium-catalyzed arene borylation. J. Am. Chem. Soc. 129, 15434-15435 (2007).
    • (2007) J. Am. Chem. Soc , vol.129 , pp. 15434-15435
    • Murphy, J.M.1    Liao, X.2    Hartwig, J.F.3
  • 13
    • 77954712560 scopus 로고    scopus 로고
    • Iridium-catalyzed C-H activation versus directed ortho metalation: Complementary borylation of aromatics and heteroaromatics
    • Hurst, T. E. et al. Iridium-catalyzed C-H activation versus directed ortho metalation: complementary borylation of aromatics and heteroaromatics. Chem. Eur. J. 16, 8155-8161 (2010).
    • (2010) Chem. Eur. J. , vol.16 , pp. 8155-8161
    • Hurst, T.E.1
  • 14
    • 84894283977 scopus 로고    scopus 로고
    • Rhodium-catalyzed intermolecular C-H silylation of arenes with high steric regiocontrol
    • Chen, C. & Hartwig, J. F. Rhodium-catalyzed intermolecular C-H silylation of arenes with high steric regiocontrol. Science 343, 853-857 (2014).
    • (2014) Science , vol.343 , pp. 853-857
    • Chen, C.1    Hartwig, J.F.2
  • 15
    • 67749142079 scopus 로고    scopus 로고
    • Pd(II)-catalyzed olefination of electron-deficient arenes using 2, 6-dialkylpyridine ligands
    • Zhang, Y.-H., Shi, B.-F. & Yu, J.-Q. Pd(II)-catalyzed olefination of electron-deficient arenes using 2, 6-dialkylpyridine ligands. J. Am. Chem. Soc. 131, 5072-5074 (2009).
    • (2009) J. Am. Chem. Soc , vol.131 , pp. 5072-5074
    • Zhang, Y.-H.1    Shi, B.-F.2    Yu, J.-Q.3
  • 16
    • 79955684836 scopus 로고    scopus 로고
    • Ligand-promoted C-3 selective C-H olefination of pyridines with Pd catalysts
    • Ye, M., Gao, G.-L. & Yu, J -Q. Ligand-promoted C-3 selective C-H olefination of pyridines with Pd catalysts. J. Am. Chem. Soc. 133, 6964-6967 (2011).
    • (2011) J. Am. Chem. Soc , vol.133 , pp. 6964-6967
    • Ye, M.1    Gao, G.-L.2    Yu, J.-Q.3
  • 17
    • 81855218279 scopus 로고    scopus 로고
    • Ligand-promoted C3-selective arylation of pyridines with Pd catalysts: Gram-scale synthesis of (±)-preclamol
    • Ye, M. et al. Ligand-promoted C3-selective arylation of pyridines with Pd catalysts: gram-scale synthesis of (±)-preclamol. J. Am. Chem. Soc. 133, 19090-19093 (2011).
    • (2011) J. Am. Chem. Soc , vol.133 , pp. 19090-19093
    • Ye, M.1
  • 18
    • 82555187153 scopus 로고    scopus 로고
    • Ruthenium-catalyzed meta sulfonation of 2-phenylpyridines
    • Saidi, O. et al. Ruthenium-catalyzed meta sulfonation of 2-phenylpyridines. J. Am. Chem. Soc. 133, 19298-19301 (2011).
    • (2011) J. Am. Chem. Soc , vol.133 , pp. 19298-19301
    • Saidi, O.1
  • 19
    • 84876484708 scopus 로고    scopus 로고
    • Meta-Selective C-H bond alkylation with secondary alkyl halides
    • Hofmann, N. & Ackermann, L. meta-Selective C-H bond alkylation with secondary alkyl halides. J. Am. Chem. Soc. 135, 5877-5884 (2013).
    • (2013) J. Am. Chem. Soc , vol.135 , pp. 5877-5884
    • Hofmann, N.1    Ackermann, L.2
  • 20
    • 62849102089 scopus 로고    scopus 로고
    • A meta-selective copper-catalyzed C-H bond arylation
    • Phipps, R. J. & Gaunt, M. J. A meta-selective copper-catalyzed C-H bond arylation. Science 323, 1593-1597 (2009).
    • (2009) Science , vol.323 , pp. 1593-1597
    • Phipps, R.J.1    Gaunt, M.J.2
  • 21
    • 78650911631 scopus 로고    scopus 로고
    • Copper(II)-catalyzed meta-selective direct arylation of α-aryl carbonyl compounds
    • Duong, H. A., Gilligan, R. E., Cooke, M. L., Phipps, R. J. & Gaunt, M. J. Copper(II)-catalyzed meta-selective direct arylation of α-aryl carbonyl compounds. Angew. Chem. Int. Ed. 50, 463-466 (2011).
    • (2011) Angew. Chem. Int. Ed , vol.50 , pp. 463-466
    • Duong, H.A.1    Gilligan, R.E.2    Cooke, M.L.3    Phipps, R.J.4    Gaunt, M.J.5
  • 22
    • 84862977089 scopus 로고    scopus 로고
    • Activation of remote meta-C-H bonds assisted by an end-on template
    • Leow, D., Li, G., Mei, T.-S. & Yu, J.-Q. Activation of remote meta-C-H bonds assisted by an end-on template. Nature 486, 518-522 (2012).
    • (2012) Nature , vol.486 , pp. 518-522
    • Leow, D.1    Li, G.2    Mei, T.-S.3    Yu, J.-Q.4
  • 23
    • 84889795240 scopus 로고    scopus 로고
    • Cross-coupling of remote meta- C-H bonds directed by a U-shaped template
    • Wan, L., Dastbaravardeh, N., Li, G. & Yu, J.-Q. Cross-coupling of remote meta- C-H bonds directed by a U-shaped template. J. Am. Chem. Soc. 135, 18056-18059 (2013).
    • (2013) J. Am. Chem. Soc , vol.135 , pp. 18056-18059
    • Wan, L.1    Dastbaravardeh, N.2    Li, G.3    Yu, J.-Q.4
  • 24
    • 84896265403 scopus 로고    scopus 로고
    • Conformation-induced remote meta-C-H activation of amines
    • Tang, R.-Y., Li, G. & Yu, J.-Q. Conformation-induced remote meta-C-H activation of amines. Nature 507, 215-220 (2014).
    • (2014) Nature , vol.507 , pp. 215-220
    • Tang, R.-Y.1    Li, G.2    Yu, J.-Q.3
  • 25
    • 33745631495 scopus 로고    scopus 로고
    • Molecuar recognition in the selective oxidation of saturated C-H bonds by dimanganese catalyst
    • Das, S., Incarvito, C. D., Crabtree, R. H. & Brudvig, G. W. Molecuar recognition in the selective oxidation of saturated C-H bonds by dimanganese catalyst. Science 312, 1941-1943 (2006).
    • (2006) Science , vol.312 , pp. 1941-1943
    • Das, S.1    Incarvito, C.D.2    Crabtree, R.H.3    Brudvig, G.W.4
  • 26
    • 11944250136 scopus 로고
    • Hydrogen bond directed cocrystallization and molecular recognition properties of diarylureas
    • Etter, M. C., Urbañczyk-Lipkowska, Z., Zia-Ebrahimi, M. & Panunto, T. W. Hydrogen bond directed cocrystallization and molecular recognition properties of diarylureas. J. Am. Chem. Soc. 112, 8415-8426 (1990).
    • (1990) J. Am. Chem. Soc , vol.112 , pp. 8415-8426
    • Etter, M.C.1    Urbañczyk-Lipkowska, Z.2    Zia-Ebrahimi, M.3    Panunto, T.W.4
  • 27
    • 0034722940 scopus 로고    scopus 로고
    • Steric and chelate directing effects in aromatic borylation
    • Cho, J.-Y., Iverson, C. N. & Smith, M. R. III. Steric and chelate directing effects in aromatic borylation. J. Am. Chem. Soc. 122, 12868-12869 (2000).
    • (2000) J. Am. Chem. Soc , vol.122 , pp. 12868-12869
    • Cho, J.-Y.1    Iverson, C.N.2    Smith, M.R.3
  • 28
    • 26844479250 scopus 로고    scopus 로고
    • Mechanism of the mild functionalization of arenes by diboron reagents catalyzed by iridium complexes. Intermediacy and chemistry of bipyridine-ligated iridium trisboryl complexes
    • Boller, T. M. et al. Mechanism of the mild functionalization of arenes by diboron reagents catalyzed by iridium complexes. Intermediacy and chemistry of bipyridine-ligated iridium trisboryl complexes. J. Am. Chem. Soc. 127, 14263-14278 (2005).
    • (2005) J. Am. Chem. Soc , vol.127 , pp. 14263-14278
    • Boller, T.M.1
  • 29
    • 0343542024 scopus 로고
    • 1H and 13C NMR studies on the interaction between N-acetyl-Lalanine methylamide and trifluoroacetic acid
    • Asakura, T. 1H and 13C NMR studies on the interaction between N-acetyl-Lalanine methylamide and trifluoroacetic acid. Makromol. Chem. 182, 1135-1145 (1981).
    • (1981) Makromol. Chem , vol.182 , pp. 1135-1145
    • Asakura, T.1
  • 30
    • 84867621126 scopus 로고    scopus 로고
    • Hydrogen-bonding thiourea organocatalysts: The privileged 3, 5-bis(trifluoromethyl)phenyl group
    • Lippert, K. M. et al. Hydrogen-bonding thiourea organocatalysts: the privileged 3, 5-bis(trifluoromethyl)phenyl group. Eur. J. Org. Chem. 5919-5927 (2012).
    • (2012) Eur. J. Org. Chem , pp. 5919-5927
    • Lippert, K.M.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.