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Volumn 22, Issue 33, 2016, Pages 11587-11592

Oxidative Addition to Gold(I) by Photoredox Catalysis: Straightforward Access to Diverse (C,N)-Cyclometalated Gold(III) Complexes

Author keywords

diazonium salts; gold(III) complexes; oxidative addition; photoredox catalysis

Indexed keywords

CATALYSIS; CHLORINE COMPOUNDS; LIGANDS; SALTS;

EID: 84979912175     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201602649     Document Type: Article
Times cited : (73)

References (87)
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    • During the preparation of this manuscript, reports by the Hashmi and Porcel groups on visible-light- and thermally-promoted synthesis of organometallic gold(III) complexes with aryldiazonium salts appeared:
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    • The success of this reaction likely results from direct photolysis of the diazonium salt with low-wavelength visible light, which is sufficient to initiate an efficient chain. Indeed, quantum yield measurements for this reaction in the absence of photocatalyst by chemical actinometry at 450 nm revealed a value of 70 (see Supporting Information for details). For a relevant discussion on such a direct photolysis pathway of aryldiazonium salts see
    • The success of this reaction likely results from direct photolysis of the diazonium salt with low-wavelength visible light, which is sufficient to initiate an efficient chain. Indeed, quantum yield measurements for this reaction in the absence of photocatalyst by chemical actinometry at 450 nm revealed a value of 70 (see Supporting Information for details). For a relevant discussion on such a direct photolysis pathway of aryldiazonium salts see: M. Majek, F. Filace, A. J. von Wangelin, Beilstein J. Org. Chem. 2014, 10, 981.
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    • Review on the photoredox activation of diazonium salts
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    • H and, P NMR measurements of equimolar solutions of 1 a and 2 a in CD, CN at room temperature indicate that binding of the pyridine to the gold center does not occur without photoredox activation.
    • 3CN at room temperature indicate that binding of the pyridine to the gold center does not occur without photoredox activation.
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    • For interesting discussions on the prevalence of radical chain processes in photoredox catalysis see, and also ref. [16].
    • For interesting discussions on the prevalence of radical chain processes in photoredox catalysis see: M. A. Cismesia, T. P. Yoon, Chem. Sci. 2015, 6, 5426 and also ref. [16].
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    • A follow-up by, P NMR in CD, Cl, at room temperature does not show significant decomposition of 4 aa after 12 h
    • This shows the stability of the metallacycle species towards possible side-reactions such as C−P reductive elimination. For recent examples of such processes see
    • A follow-up by31P NMR in CD2Cl2at room temperature does not show significant decomposition of 4 aa after 12 h. This shows the stability of the metallacycle species towards possible side-reactions such as C−P reductive elimination. For recent examples of such processes see: H. Kawai, W. J. Wolf, A. G. DiPasquale, M. S. Winston, F. D. Toste, J. Am. Chem. Soc. 2016, 138, 587.
    • (2016) J. Am. Chem. Soc. , vol.138 , pp. 587
    • Kawai, H.1    Wolf, W.J.2    DiPasquale, A.G.3    Winston, M.S.4    Toste, F.D.5
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    • CCDC-1483277 (3 aa), CCDC-1483278 (3 ae), CCDC-1483279 (3 ai), and CCDC-1483280 (5 aa) contain the supplementary crystallographic data for this paper
    • CCDC-1483277 (3 aa), CCDC-1483278 (3 ae), CCDC-1483279 (3 ai), and CCDC-1483280 (5 aa) 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.
    • These data can be obtained free of charge from The Cambridge Crystallographic Data


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.