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Volumn 13, Issue 12, 2011, Pages 3218-3221

Cascade intramolecular N-arylation/intermolecular carboamination reactions for the construction of tricyclic heterocycles

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; HALOGENATED HYDROCARBON; HETEROCYCLIC COMPOUND; NITROGEN; PALLADIUM;

EID: 79958818179     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol201123b     Document Type: Article
Times cited : (30)

References (36)
  • 3
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    • For selected recent examples, see
    • For selected recent examples, see: Ohmura, T.; Kijima, A.; Suginome, M. Org. Lett. 2011, 13, 1238
    • (2011) Org. Lett. , vol.13 , pp. 1238
    • Ohmura, T.1    Kijima, A.2    Suginome, M.3
  • 10
    • 33846644502 scopus 로고    scopus 로고
    • For reviews on Pd-catalyzed carboamination reactions between aryl/alkenyl halides and amines bearing pendant alkenes, see
    • For reviews on Pd-catalyzed carboamination reactions between aryl/alkenyl halides and amines bearing pendant alkenes, see: Wolfe, J. P. Eur. J. Org. Chem. 2007, 571
    • (2007) Eur. J. Org. Chem. , pp. 571
    • Wolfe, J.P.1
  • 12
    • 79958838083 scopus 로고    scopus 로고
    • note
    • 2 promotes rapid N -arylation and disfavors carboamination. When Dpe-Phos is added, a new catalyst is generated that facilitates the carboamination step. For further discussion, see ref 3a.
  • 13
    • 77952401842 scopus 로고    scopus 로고
    • For further discussion of transition states leading to fused bicyclic compounds in Pd-catalyzed alkene carboamination reactions, see
    • For further discussion of transition states leading to fused bicyclic compounds in Pd-catalyzed alkene carboamination reactions, see: Lemen, G. S.; Wolfe, J. P. Org. Lett. 2010, 12, 2322
    • (2010) Org. Lett. , vol.12 , pp. 2322
    • Lemen, G.S.1    Wolfe, J.P.2
  • 15
    • 77950997306 scopus 로고    scopus 로고
    • For Pd-catalyzed carboamination reactions involving aryl chloride electrophiles, see
    • For Pd-catalyzed carboamination reactions involving aryl chloride electrophiles, see: Rosen, B. R.; Ney, J. E.; Wolfe, J. P. J. Org. Chem. 2010, 75, 2756
    • (2010) J. Org. Chem. , vol.75 , pp. 2756
    • Rosen, B.R.1    Ney, J.E.2    Wolfe, J.P.3
  • 22
    • 79955390732 scopus 로고    scopus 로고
    • For other recent complementary approaches to the synthesis of hexahydropyrroloquinolines and tetrahydropyrroloindoles structurally related to 8a - l, see
    • For other recent complementary approaches to the synthesis of hexahydropyrroloquinolines and tetrahydropyrroloindoles structurally related to 8a - l, see: Kip, K.-T.; Yang, D. Org. Lett. 2011, 13, 2134
    • (2011) Org. Lett. , vol.13 , pp. 2134
    • Kip, K.-T.1    Yang, D.2
  • 30
    • 79958850928 scopus 로고    scopus 로고
    • Hydrazine substrate 16 was prepared in four steps from 2-bromobenzyl bromide, tert -butyl carbazate, benzaldehyde, and allylmagnesium bromide
    • Hydrazine substrate 16 was prepared in four steps from 2-bromobenzyl bromide, tert -butyl carbazate, benzaldehyde, and allylmagnesium bromide.
  • 31
    • 79958801606 scopus 로고    scopus 로고
    • See the Supporting Information for complete experimental details
    • See the Supporting Information for complete experimental details.
  • 34
    • 79958847214 scopus 로고    scopus 로고
    • Small differences in enantiopurity between substrates and products are attributed to experimental error resulting from a necessary use of Mosher amide NMR analysis to assay substrate enantiopurities. The enantiopurities of products were assayed by HPLC analysis
    • Small differences in enantiopurity between substrates and products are attributed to experimental error resulting from a necessary use of Mosher amide NMR analysis to assay substrate enantiopurities. The enantiopurities of products were assayed by HPLC analysis.
  • 35
    • 79958857043 scopus 로고    scopus 로고
    • 4 was used as a ligand for this transformation
    • 4 was used as a ligand for this transformation.
  • 36
    • 63049129047 scopus 로고    scopus 로고
    • 4Dpe-Phos in metal-catalyzed reactions (the Pd-catalyzed N -arylation of 4-bromoacetophenone with five different amines). See ref 15b. In general, the reactivity of electron-rich wide bite angle phosphine ligands in catalytic transformations has rarely been examined. For additional discussion, see
    • 4Dpe-Phos in metal-catalyzed reactions (the Pd-catalyzed N -arylation of 4-bromoacetophenone with five different amines). See ref 15b. In general, the reactivity of electron-rich wide bite angle phosphine ligands in catalytic transformations has rarely been examined. For additional discussion, see: Birkholz, M.-N.; Freixa, Z.; van Leeuwen, P. W. N. M. Chem. Soc. Rev. 2009, 38, 1099
    • (2009) Chem. Soc. Rev. , vol.38 , pp. 1099
    • Birkholz, M.-N.1    Freixa, Z.2    Van Leeuwen, P.W.N.M.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.