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Volumn 20, Issue 41, 2014, Pages 13127-13131

Stereoselective C-H Borylations of Cyclopropanes and Cyclobutanes with Silica-Supported Monophosphane-Ir Catalysts

Author keywords

borylation; C H activation; cyclobutanes; cyclopropanes; iridium catalysts

Indexed keywords

ACTIVATION ANALYSIS; CATALYSTS; PROPANE; SILICA; STEREOSELECTIVITY;

EID: 84941103336     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201404362     Document Type: Article
Times cited : (63)

References (86)
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    • For cyclopropanes, see
    • For cyclopropanes, see:
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    • (Eds.: S. Patai, Z. Rappoport), Wiley, Chichester
    • The Chemistry of the Cyclopropyl Group (Eds.:, S. Patai, Z. Rappoport,), Wiley, Chichester, 1987;
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    • 84958010430 scopus 로고    scopus 로고
    • For cyclobutanes, see
    • For cyclobutanes, see:
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    • (Eds.: Z. Rappoport, J. F. Liebman), Wiley, Chichester
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    • (2005) The Chemistry of Cyclobutanes
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    • Metal-catalyzed C-H functionalizations of cyclopropanes
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    • Metal-catalyzed C-H functionalizations of cyclobutanes
    • Metal-catalyzed C-H functionalizations of cyclobutanes:
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    • Stoichiometric C-H funtionalizations of cyclopropanes and cyclobutanes with organolithium or organomagnesium reagents
    • Stoichiometric C-H funtionalizations of cyclopropanes and cyclobutanes with organolithium or organomagnesium reagents:
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    • Recent reviews on transition-metal-catalyzed C-H borylation
    • Recent reviews on transition-metal-catalyzed C-H borylation:
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    • Organoboron compounds as biologically active molecules.
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    • 3)-H borylations
    • 3)-H borylations:
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    • 3)-H borylations
    • 3)-H borylations:
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    • For C-C bond-forming transformations of cyclopropyl- and cyclobutyltrifluoroborates, see:
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    • 84958010438 scopus 로고    scopus 로고
    • Silica-SMAP and Silica-TRIP can be purchased from Wako Pure Chemical Industries. For their applications, see refs. [10b,c].
    • Silica-SMAP and Silica-TRIP can be purchased from Wako Pure Chemical Industries. For their applications, see refs. [10b,c].
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    • For the stereoselective synthesis of cyclopropyl- and cyclobutylboronates through copper-catalyzed reactions of allyl and homoallyl alcohol derivatives with 2, see
    • For the stereoselective synthesis of cyclopropyl- and cyclobutylboronates through copper-catalyzed reactions of allyl and homoallyl alcohol derivatives with 2, see:
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    • See the Supporting Information for ligand effects.
    • See the Supporting Information for ligand effects.
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    • The reaction using HBpin instead of 2 under otherwise identical reaction conditions gave 3 a in 77 % yield.
    • The reaction using HBpin instead of 2 under otherwise identical reaction conditions gave 3 a in 77 % yield.
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    • 11B NMR spectroscopic analysis (see the Supporting Information). See also
    • 11B NMR spectroscopic analysis (see the Supporting Information). See also:
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    • 84958010443 scopus 로고    scopus 로고
    • CCDC-1005180 (3 a′), CCDC-1005181 (3 j), CCDC-1005182 (5 b), and CCDC-1005183 (8 a) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via. See the Supporting Information for details.
    • CCDC-1005180 (3 a′), CCDC-1005181 (3 j), CCDC-1005182 (5 b), and CCDC-1005183 (8 a) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif. See the Supporting Information for details.
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    • The crude reaction mixture contained a significant amount of a byproduct (2-cyclopropyl-1-methyl-2,3-dihydro-1H-benzoimidazole, 39 %) resulting from C=N reduction of the starting material (1 e); however, the borylation product 3 e did not undergo C=N reduction.
    • The crude reaction mixture contained a significant amount of a byproduct (2-cyclopropyl-1-methyl-2,3-dihydro-1H-benzoimidazole, 39 %) resulting from C=N reduction of the starting material (1 e); however, the borylation product 3 e did not undergo C=N reduction. Therefore, 3 e could be isolated easily by bulb-to-bulb distillation.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.