메뉴 건너뛰기




Volumn 127, Issue 24, 2005, Pages 8644-8651

Selective synthesis of 5- or 6-aryl octahydrocyclopenta[b]pyrroles from a common precursor through control of competing pathways in a Pd-catalyzed reaction

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; COMPLEXATION; REACTION KINETICS; REDUCTION; SYNTHESIS (CHEMICAL);

EID: 20944448962     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0430346     Document Type: Article
Times cited : (128)

References (91)
  • 7
    • 4544265647 scopus 로고    scopus 로고
    • A portion of this work has been previously communicated. See: Ney, J. E.; Wolfe, J. P. Angew. Chem., Int. Ed. 2004, 43, 3605-3608.
    • (2004) Angew. Chem., Int. Ed. , vol.43 , pp. 3605-3608
    • Ney, J.E.1    Wolfe, J.P.2
  • 8
    • 7444269099 scopus 로고    scopus 로고
    • For related transformations that provide indolines or tetrahydrofurans, see: (a) Lira, R.; Wolfe, J. P. J. Am. Chem. Soc. 2004, 126, 13906-13907.
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 13906-13907
    • Lira, R.1    Wolfe, J.P.2
  • 11
    • 13644249121 scopus 로고    scopus 로고
    • For recent, complementary methods involving late transition metal-catalyzed synthesis of pyrrolidines from γ-aminoalkenes, see: (a) Bender, C. F.; Widenhoefer, R. A. J. Am. Chem. Soc. 2005, 127, 1070-1071.
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 1070-1071
    • Bender, C.F.1    Widenhoefer, R.A.2
  • 14
    • 0242563114 scopus 로고    scopus 로고
    • Astruc, D., Ed.; Wiley-VCH: Weinheim, Germany
    • (b) Hartwig, J. F. In Modern Arene Chemistry; Astruc, D., Ed.; Wiley-VCH: Weinheim, Germany, 2002; p 107.
    • (2002) Modern Arene Chemistry , pp. 107
    • Hartwig, J.F.1
  • 20
    • 0011498766 scopus 로고
    • For examples of alkene insertion into Pt-N bonds see: (a) Cowan, R. L.; Trogler, W. C. Organometallics 1987, 6, 2451-2453.
    • (1987) Organometallics , vol.6 , pp. 2451-2453
    • Cowan, R.L.1    Trogler, W.C.2
  • 22
    • 33845280868 scopus 로고
    • For an example of a catalytic reaction that likely proceeds via insertion of norbornene into an Ir-N bond, see: Casalnuovo, A. L.; Calabrese, J. C.; Milstein, D. J. Am. Chem. Soc. 1988, 110, 6738-6744.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 6738-6744
    • Casalnuovo, A.L.1    Calabrese, J.C.2    Milstein, D.3
  • 26
    • 15044342205 scopus 로고    scopus 로고
    • For recent synthetic approaches to the 1-azabicyclo[3.3.0]octane ring system, see: (a) Aron, Z. D.; Overman, L. E. Org. Lett. 2005, 7, 913-916.
    • (2005) Org. Lett. , vol.7 , pp. 913-916
    • Aron, Z.D.1    Overman, L.E.2
  • 34
    • 20944441999 scopus 로고    scopus 로고
    • note
    • Dppe = 1,2-bis(diphenylphosphino)ethane, dppp = 1,3- bis(diphenylphosphino)propane, dppb = 1,4-bis(diphenylphosphino)butane, dppm = 1,1-bis(diphenylphosphino)methane, dpp-benzene = 1,2-bis(diphenylphosphino) benzene, dcpe = 1,2-bis(dicydohexylphosphino)ethane, BINAP = (±)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl, dpe-phos = bis(2-diphenylphosphinophenyl)ether, dppf = 1,1′- bis(diphenylphosphinoferrocene), xantphos = 9,9-dimethyl-4,5- bis(diphenylphosphino)xanthene.
  • 35
    • 20944447030 scopus 로고    scopus 로고
    • note
    • Our previous studies showed that use of certain electron-rich phosphines (e.g., 2-dicyclohexylphosphinobiphenyl) provided acceptable yields in the Pd-catalyzed carboamination reactions of γ-aminoalkenes. Thus, it seemed possible that the alkene insertion into the Pd-N bond may also potentially proceed with other electron-rich phosphines. See ref 2.
  • 37
    • 0012253713 scopus 로고    scopus 로고
    • and references therein
    • (b) Steinhoff, B. A.; Stahl, S. S. Org. Lett. 2002, 4, 4179-4181 and references therein.
    • (2002) Org. Lett. , vol.4 , pp. 4179-4181
    • Steinhoff, B.A.1    Stahl, S.S.2
  • 40
    • 20944434812 scopus 로고    scopus 로고
    • note
    • The rate of C-N bond-forming reductive elimination decreases as the nitrogen becomes less nucleophilic. See: (a) Reference 12b.
  • 44
    • 12344337689 scopus 로고    scopus 로고
    • The rate of reductive elimination generally increases as ligand size increases and decreases as ligand basicity increases. Steric effects can outweigh electronic effects, as electron-rich ligands that are sterically bulky are known to promote reductive elimination. For reviews, see: (a) Christmann, U.; Vilar, R. Angew. Chem., Int. Ed. 2005, 44, 366-374.
    • (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 366-374
    • Christmann, U.1    Vilar, R.2
  • 46
    • 0035965688 scopus 로고    scopus 로고
    • and references therein
    • 8-Pd(II) complexes generally occur via an associative mechanism. See: (a) Shultz, L. H.; Tempel, D. J.; Brookhart, M. J. Am. Chem. Soc. 2001, 123, 11539-11555 and references therein.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 11539-11555
    • Shultz, L.H.1    Tempel, D.J.2    Brookhart, M.3
  • 49
    • 20944437684 scopus 로고    scopus 로고
    • note
    • Rates of associative ligand substitution should decrease as the electron density on the metal center increases due to electron-electron repulsion between the metal and the incoming nucleophile.
  • 50
    • 0345352298 scopus 로고
    • Increased back-bonding from the electron-rich metal to the alkene may also play a role in decreasing the rate of alkene dissociation. For a discussion of back-bonding in electron-rich Pd(II)-alkene complexes, see: Miki, K.; Shiotani, O.; Kai, Y.; Kasai, N.; Kanatani, H.; Kurosawa, H. Organometallics 1983, 2, 585-593.
    • (1983) Organometallics , vol.2 , pp. 585-593
    • Miki, K.1    Shiotani, O.2    Kai, Y.3    Kasai, N.4    Kanatani, H.5    Kurosawa, H.6
  • 51
    • 0035961019 scopus 로고    scopus 로고
    • Most air-sensitive trialkylphosphine ligands were employed in the form of their air-stable, crystalline tetrafluoroborate salts. See: Netherton, M. R.; Fu, G. C. Org. Lett. 2001, 3, 4295-4298.
    • (2001) Org. Lett. , vol.3 , pp. 4295-4298
    • Netherton, M.R.1    Fu, G.C.2
  • 56
    • 20944446914 scopus 로고    scopus 로고
    • note
    • 3.
  • 58
    • 20944440644 scopus 로고    scopus 로고
    • note
    • Use of trimesitylphosphine provided a very complex mixture of unidentified products.
  • 67
    • 20944445114 scopus 로고    scopus 로고
    • note
    • For other examples of Pd-catalyzed oxidative animation reactions of olefins, see: (a) Reference 6e.
  • 72
    • 20944434247 scopus 로고    scopus 로고
    • note
    • 3 as ligands afforded isolated yields of 54, 44, and 53%, respectively.
  • 73
    • 20944444913 scopus 로고    scopus 로고
    • note
    • 1H NMR). The small differences in the product ratios for these are likely due to experimental error associated with the measurement techniques.
  • 74
    • 20944437151 scopus 로고    scopus 로고
    • note
    • The mechanism for Pd-catalyzed N-arylation reactions of amines is well-documented and is believed to proceed via intermediate palladium(aryl) (amido) complexes such as 6. For lead references, see: (a) Reference 5.
  • 79
    • 0034025998 scopus 로고    scopus 로고
    • Intermolecular Heck arylations of substituted cyclic, bicyclic, or heterocyclic alkenes generally provide products resulting from arylation on the less hindered face of the double bond. See: (a) Tietze, L. F.; Petersen, S. Eur. J. Org. Chem. 2000, 1827-1830.
    • (2000) Eur. J. Org. Chem. , pp. 1827-1830
    • Tietze, L.F.1    Petersen, S.2
  • 86
    • 20944445977 scopus 로고    scopus 로고
    • note
    • 4 or dppp at 110 °C in toluene did not result in any detectable reaction.
  • 90
    • 0037138687 scopus 로고    scopus 로고
    • and references therein
    • Ligand 11 is believed to act as a bidentate ligand via complexation of the aromatic ring bearing the dimethylamino group. See: Yin, J.; Rainka, M. P.; Zhang, X.-X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 1162-1163 and references therein.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 1162-1163
    • Yin, J.1    Rainka, M.P.2    Zhang, X.-X.3    Buchwald, S.L.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.