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Volumn 80, Issue 13, 2015, Pages 6794-6813

Generating Active L-Pd(0) via Neutral or Cationic π-Allylpalladium Complexes Featuring Biaryl/Bipyrazolylphosphines: Synthetic, Mechanistic, and Structure-Activity Studies in Challenging Cross-Coupling Reactions

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; CHEMICAL ACTIVATION; CHEMICAL REACTIONS; LIGANDS; SCAFFOLDS; SINGLE CRYSTALS;

EID: 84941063036     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/acs.joc.5b01005     Document Type: Article
Times cited : (150)

References (111)
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    • The 2nd and 3rd generation palladacycle precatalysts have also been prepared with bidentate bisphosphine ligands, which likely generate -2 L2Pd(0)upon activation. See ref 13c and
    • The 2nd and 3rd generation palladacycle precatalysts have also been prepared with bidentate bisphosphine ligands, which likely generate -2 L2Pd(0)upon activation. See ref 13c and Friis, S. D.; Skrydstrup, T.; Buchwald, S. L. Org. Lett. 2014, 16, 4296
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    • After submission of this manuscript, Buchwald et. al. noted inhibition due to carbazole in the arylation of α-branched secondary amines. See
    • After submission of this manuscript, Buchwald et. al. noted inhibition due to carbazole in the arylation of α-branched secondary amines. See: Park, N. H.; Vinogradova, E. V.; Surry, D. S.; Buchwald, S. L. Angew. Chem., Int. Ed. 2015, 10.1002/anie.201502626
    • (2015) Angew. Chem., Int. Ed.
    • Park, N.H.1    Vinogradova, E.V.2    Surry, D.S.3    Buchwald, S.L.4
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    • After the submission of this manuscript, Hazari et al. reported related studies using a η3-1-t-Bu-indenyl scaffold. See
    • After the submission of this manuscript, Hazari et al. reported related studies using a η3-1-t-Bu-indenyl scaffold. See: Melvin, P. R.; Nova, A.; Balcells, D.; Dai, W.; Hazari, N.; Hruszkewycz, D. P.; Shah, H. P.; Tudge, M. T. ACS Catal. 2015, 5, 3680
    • (2015) ACS Catal. , vol.5 , pp. 3680
    • Melvin, P.R.1    Nova, A.2    Balcells, D.3    Dai, W.4    Hazari, N.5    Hruszkewycz, D.P.6    Shah, H.P.7    Tudge, M.T.8
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    • A (pyrimidinium betaine-functionalized ligand)Pd(allyl)Cl complex has been recently reported. See
    • A (pyrimidinium betaine-functionalized ligand)Pd(allyl)Cl complex has been recently reported. See: Noël-Duchesneau, L.; Lugan, N.; Lavigne, G.; Labande, A.; César, V. Organometallics 2014, 33, 5085
    • (2014) Organometallics , vol.33 , pp. 5085
    • Noël-Duchesneau, L.1    Lugan, N.2    Lavigne, G.3    Labande, A.4    César, V.5
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    • The addition of an extra equivalent of ligand relative to Pd has been shown to be beneficial in C-N cross-coupling reactions, particularly those with low catalyst loadings or long reaction times. For a discussion, see
    • The addition of an extra equivalent of ligand relative to Pd has been shown to be beneficial in C-N cross-coupling reactions, particularly those with low catalyst loadings or long reaction times. For a discussion, see: Surry, D. S.; Buchwald, S. L. Chem. Sci. 2011, 2, 27
    • (2011) Chem. Sci. , vol.2 , pp. 27
    • Surry, D.S.1    Buchwald, S.L.2
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    • For an elegant study on the competitive roles of amine binding affinity and acidity on the selectivity in C-N cross-coupling reactions, see
    • For an elegant study on the competitive roles of amine binding affinity and acidity on the selectivity in C-N cross-coupling reactions, see: Biscoe, M. R.; Barder, T. E.; Buchwald, S. L. Angew. Chem., Int. Ed. 2007, 46, 7232
    • (2007) Angew. Chem., Int. Ed. , vol.46 , pp. 7232
    • Biscoe, M.R.1    Barder, T.E.2    Buchwald, S.L.3
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    • Buchwald et. al. have recently described the inhibitory effects of Pd(II)-azoyl species in Suzuki-Miyaura reactions. See
    • Buchwald et. al. have recently described the inhibitory effects of Pd(II)-azoyl species in Suzuki-Miyaura reactions. See: Düfert, M. A.; Billingsley, K. L.; Buchwald, S. L. J. Am. Chem. Soc. 2013, 135, 12877
    • (2013) J. Am. Chem. Soc. , vol.135 , pp. 12877
    • Düfert, M.A.1    Billingsley, K.L.2    Buchwald, S.L.3
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    • Cone angle for PhP(t-Bu)2 See
    • Cone angle for PhP(t-Bu)2. See: Tolman, C. A. Chem. Rev. 1977, 77, 313
    • (1977) Chem. Rev. , vol.77 , pp. 313
    • Tolman, C.A.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.