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Volumn 54, Issue 5, 2015, Pages 1646-1650

Palladium-catalyzed intramolecular C-H difluoroalkylation: Synthesis of substituted 3,3-difluoro-2-oxindoles

Author keywords

C H activation; Cross coupling; Fluorine; Heterocycles; Palladium

Indexed keywords

ACTIVATION ANALYSIS; FLUORINE; PALLADIUM;

EID: 84921491083     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201410471     Document Type: Article
Times cited : (85)

References (86)
  • 7
    • 84885450024 scopus 로고    scopus 로고
    • Angew. Chem. 2013, 125, 8372-8423
    • (2013) Angew. Chem. , vol.125 , pp. 8372-8423
  • 10
    • 84865840392 scopus 로고    scopus 로고
    • Angew. Chem. 2012, 124, 5134-5136
    • (2012) Angew. Chem. , vol.124 , pp. 5134-5136
  • 13
    • 79955651634 scopus 로고    scopus 로고
    • Angew. Chem. 2010, 122, 9510-9512
    • (2010) Angew. Chem. , vol.122 , pp. 9510-9512
  • 14
    • 83055177179 scopus 로고    scopus 로고
    • for selected examples of arene fluorination and trifluoromethylation, see: f)
    • for selected examples of arene fluorination and trifluoromethylation, see: f) D. A. Nagib, D. W. C. MacMillan, Nature 2011, 480, 224-228
    • (2011) Nature , vol.480 , pp. 224-228
    • Nagib, D.A.1    MacMillan, D.W.C.2
  • 27
    • 84897975122 scopus 로고    scopus 로고
    • Angew. Chem. 2013, 125, 11842-11845.
    • (2013) Angew. Chem. , vol.125 , pp. 11842-11845
  • 32
    • 84887535761 scopus 로고    scopus 로고
    • Angew. Chem. 2012, 124, 12256-12260
    • (2012) Angew. Chem. , vol.124 , pp. 12256-12260
  • 35
    • 84893435678 scopus 로고    scopus 로고
    • during the preparation of this manuscript, the following metal-catalyzed difluoroalkylation reactions were reported: g)
    • during the preparation of this manuscript, the following metal-catalyzed difluoroalkylation reactions were reported: g) Q.-Q. Min, Z. Yin, Z. Feng, W.-H. Guo, X. Zhang, J. Am. Chem. Soc. 2014, 136, 1230-1233
    • (2014) J. Am. Chem. Soc. , vol.136 , pp. 1230-1233
    • Min, Q.-Q.1    Yin, Z.2    Feng, Z.3    Guo, W.-H.4    Zhang, X.5
  • 38
    • 84921464665 scopus 로고    scopus 로고
    • Angew. Chem. 2014, 126, 1695-1699
    • (2014) Angew. Chem. , vol.126 , pp. 1695-1699
  • 40
    • 84921499380 scopus 로고    scopus 로고
    • Angew. Chem. 2014, 126, 10067-10071
    • (2014) Angew. Chem. , vol.126 , pp. 10067-10071
  • 42
    • 84941600716 scopus 로고    scopus 로고
    • Angew. Chem. 2014, 126, 10625-10629
    • (2014) Angew. Chem. , vol.126 , pp. 10625-10629
  • 48
    • 79955419410 scopus 로고    scopus 로고
    • For a discussion on bioisosteres, see:
    • For a discussion on bioisosteres, see: N A. Meanwell, J. Med. Chem. 2011, 54, 2529-2591.
    • (2011) J. Med. Chem. , vol.54 , pp. 2529-2591
    • Meanwell, N.A.1
  • 62
    • 84885166387 scopus 로고    scopus 로고
    • Angew. Chem. 2013, 125, 4041-4044
    • (2013) Angew. Chem. , vol.125 , pp. 4041-4044
  • 67
    • 84894495048 scopus 로고    scopus 로고
    • For recent examples of C-H trifluoroethylation, see: g)
    • For recent examples of C-H trifluoroethylation, see: g) W Song, S. Lackner, L. Ackermann, Angew. Chem. Int. Ed. 2014, 53, 2477-2480
    • (2014) Angew. Chem. Int. Ed. , vol.53 , pp. 2477-2480
    • Song, W.1    Lackner, S.2    Ackermann, L.3
  • 68
    • 84905574706 scopus 로고    scopus 로고
    • Angew. Chem. 2014, 126, 2510-2513
    • (2014) Angew. Chem. , vol.126 , pp. 2510-2513
  • 70
    • 84921465781 scopus 로고    scopus 로고
    • Angew. Chem. 2014, 126, 10338-10342.
    • (2014) Angew. Chem. , vol.126 , pp. 10338-10342
  • 74
    • 85028174889 scopus 로고    scopus 로고
    • To the best of our knowledge, the oxidative addition of palladium to a C-Cl bond of a difluoroalkyl chloride has not been described in the literature. The palladium-catalyzed difluoroalkylation reactions using difluoroalkyl bromides have been reported. See Ref. [5g,i,k]
    • To the best of our knowledge, the oxidative addition of palladium to a C-Cl bond of a difluoroalkyl chloride has not been described in the literature. The palladium-catalyzed difluoroalkylation reactions using difluoroalkyl bromides have been reported. See Ref. [5g,i,k].
  • 77
    • 0034712161 scopus 로고    scopus 로고
    • The beneficial effects of catalyst premixing have been reported previously. See: a)
    • The beneficial effects of catalyst premixing have been reported previously. See: a) J. P. Wolfe, S. L. Buchwald, J. Org. Chem. 2000, 65, 1144-1157
    • (2000) J. Org. Chem. , vol.65 , pp. 1144-1157
    • Wolfe, J.P.1    Buchwald, S.L.2
  • 79
    • 84867085662 scopus 로고    scopus 로고
    • Angew. Chem. 2011, 123, 9106-9109
    • (2011) Angew. Chem. , vol.123 , pp. 9106-9109
  • 83
    • 84858776560 scopus 로고    scopus 로고
    • For a useful discussion on analyzing KIE, see:
    • For a useful discussion on analyzing KIE, see: E. M. Simmons, J. F. Hartwig, Angew. Chem. Int. Ed. 2012, 51, 3066-3072
    • (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 3066-3072
    • Simmons, E.M.1    Hartwig, J.F.2
  • 84
    • 84863668849 scopus 로고    scopus 로고
    • Angew. Chem. 2012, 124, 3120-3126.
    • (2012) Angew. Chem. , vol.124 , pp. 3120-3126
  • 85
    • 30344442774 scopus 로고    scopus 로고
    • 3-carbon atom rehybridization in an arene dearomatization step
    • 3-carbon atom rehybridization in an arene dearomatization step: J. A. Tunge, L. N. Foresee, Organometallics 2005, 24, 6440-6444.
    • (2005) Organometallics , vol.24 , pp. 6440-6444
    • Tunge, J.A.1    Foresee, L.N.2
  • 86
    • 85028145549 scopus 로고    scopus 로고
    • An alternative mechanism in which C - C bond formation proceeds by carbopalladation of the aromatic ring followed by β-hydride elimination cannot be excluded. See Ref. [12]
    • An alternative mechanism in which C - C bond formation proceeds by carbopalladation of the aromatic ring followed by β-hydride elimination cannot be excluded. See Ref. [12].


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.