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Volumn 133, Issue 18, 2011, Pages 6956-6959

Ligand steric contours to understand the effects of N-heterocyclic carbene ligands on the reversal of regioselectivity in Ni-catalyzed reductive couplings of alkynes and aldehydes

Author keywords

[No Author keywords available]

Indexed keywords

CARBENES; CONTOUR MAP; N-HETEROCYCLIC CARBENE LIGANDS; NHC LIGANDS; REDUCTIVE COUPLING REACTION; REDUCTIVE COUPLINGS; STERIC HINDRANCES; STERIC INFLUENCE;

EID: 79955678637     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja202007s     Document Type: Article
Times cited : (113)

References (45)
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    • This strategy is exemplified by the acid-catalyzed hydration of olefins compared with hydroboration-oxidation protocols
    • This strategy is exemplified by the acid-catalyzed hydration of olefins compared with hydroboration-oxidation protocols.
  • 11
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    • Reviews of Ni-catalyzed reductive alkyne-aldehyde couplings: (1) (a) Montgomery, J. Acc. Chem. Res. 2000, 33, 467.
    • (2000) Acc. Chem. Res. , vol.33 , pp. 467
    • Montgomery, J.1
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    • Other notable recent examples of regiochemical reversals: (1) (a) Gao, F.; Hoveyda, A. H. J. Am. Chem. Soc. 2010, 132, 10961.
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 10961
    • Gao, F.1    Hoveyda, A.H.2
  • 24
    • 77950202768 scopus 로고    scopus 로고
    • The effects of N-substituents on the flexibility and conformations of NHC ligands were investigated in a recent dynamical study: Ragone, F.; Poater, A.; Cavallo, L. J. Am. Chem. Soc. 2010, 132, 4249.
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 4249
    • Ragone, F.1    Poater, A.2    Cavallo, L.3
  • 25
    • 57549119091 scopus 로고    scopus 로고
    • The conformational flexibility of NHC ligands can facilitate some Pd-catalyzed cross-coupling reactions: Wurtz, S.; Glorius, F. Acc. Chem. Res. 2008, 41, 1523.
    • (2008) Acc. Chem. Res. , vol.41 , pp. 1523
    • Wurtz, S.1    Glorius, F.2
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    • For an illustration of how stereoselective olefin polymerizations can be evaluated by %Vbur, see: Poater, A.; Cavallo, L. Dalton Trans. 2009, 8878.
    • (2009) Dalton Trans. , pp. 8878
    • Poater, A.1    Cavallo, L.2
  • 27
    • 3342989847 scopus 로고    scopus 로고
    • For an early illustration of regiocontrol imparted by NHC size in a Ni-catalyzed cyclization, see: Tekavec, T. N.; Arif, A. M.; Louie, J. Tetrahedron 2004, 60, 7431.
    • (2004) Tetrahedron , vol.60 , pp. 7431
    • Tekavec, T.N.1    Arif, A.M.2    Louie, J.3
  • 30
  • 31
    • 79953874235 scopus 로고    scopus 로고
    • (d) Review of theoretical studies of regioselectivity of C-C bond-forming reactions: Liu, P; Houk, K. N. Inorg. Chim. Acta 2011, 369, 2.
    • (2011) Inorg. Chim. Acta , vol.369 , pp. 2
    • Liu, P.1    Houk, K.N.2
  • 32
    • 79955698998 scopus 로고    scopus 로고
    • (a) The full catalytic cycle of Ni-catalyzed alkyne-aldehyde couplings using NHC ligand and organosilane as reductant was calculated using B3LYP/LANL2DZ-6-31G(1) (d) and is included in the Supporting Information
    • (a) The full catalytic cycle of Ni-catalyzed alkyne-aldehyde couplings using NHC ligand and organosilane as reductant was calculated using B3LYP/LANL2DZ-6-31G(1) (d) and is included in the Supporting Information.
  • 33
    • 79954488900 scopus 로고    scopus 로고
    • (b) Kinetic study of Ni(NHC)-catalyzed ynal cyclizations using organosilane reductant is also consistent with the oxidative cyclization mechanism: Baxter, R. D.; Montgomery, J. J. Am. Chem. Soc. 2011, 133, 5728-5731.
    • (2011) J. Am. Chem. Soc. , vol.133 , pp. 5728-5731
    • Baxter, R.D.1    Montgomery, J.2
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    • bur calculations
    • bur calculations.
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    • The z axis is defined as the axis along the center of the forming C-C bond and the Ni atom
    • The z axis is defined as the axis along the center of the forming C-C bond and the Ni atom.
  • 42
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    • (a) For a related theoretical study of 2D contour plots of NHC ligands, see ref 9
    • (a) For a related theoretical study of 2D contour plots of NHC ligands, see ref 9.
  • 44
    • 79955684983 scopus 로고    scopus 로고
    • "X" is the position of the carbon atom on the distal alkyne substituent that is directly bonded to the triple bond
    • "X" is the position of the carbon atom on the distal alkyne substituent that is directly bonded to the triple bond.
  • 45
    • 79955697318 scopus 로고    scopus 로고
    • This could be observed in the steric contours of these ligands; see Supporting Information for details
    • This could be observed in the steric contours of these ligands; see Supporting Information for details.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.