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Volumn 70, Issue 20, 2005, Pages 8017-8026

Indirect electroreductive cyclization and electrohydrocyclization using catalytic reduced nickel(II) salen

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; CARBON; CATALYSIS; ELECTROCHEMISTRY; MOLECULAR STRUCTURE; NICKEL;

EID: 25444450361     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo051148+     Document Type: Article
Times cited : (70)

References (65)
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    • (c) Molander, G. A. Samarium(II) Mediated Radical Reactions. In Radicals in Organic Synthesis; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, Germany, 2000; Vol. 1, Chapter 2.1, pp 153-182 and references therein.
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    • Wiley & Sons: New York, Collect.
    • (b) Schreiber, S. L.; Claus, R. E. Organic Syntheses; Wiley & Sons: New York, 1990; Collect. Vol. 7, pp 168-173.
    • (1990) Organic Syntheses , vol.7 , pp. 168-173
    • Schreiber, S.L.1    Claus, R.E.2
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    • Electrogenerated reagents
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    • (b) Simonet, J.; Pilard, J.-F. Electrogenerated reagents. In Organic Electrochemistry, 4th ed.; Lund, H., Hammerich, O., Eds.; Dekker: New York, 2001; pp 1163-1225.
    • (2001) Organic Electrochemistry, 4th Ed. , pp. 1163-1225
    • Simonet, J.1    Pilard, J.-F.2
  • 29
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    • note
    • (b) In many respects, the situation is similar to acid-base chemistry wherein even though an initial acid-base equilibrium might reside on the left, follow-up reactions can drive the equilibrium toward the product.
  • 36
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    • 226th American Chemical Society National Meeting, New York, Sept. 7-11; American Chemical Society: Washington, DC; ORGN-638
    • (e) Peters, D. G. Using transition-metal complexes as catalysts for organic electrochemistry, 226th American Chemical Society National Meeting, New York, Sept. 7-11, 2003; American Chemical Society: Washington, DC, 2003; ORGN-638.
    • (2003) Using Transition-metal Complexes as Catalysts for Organic Electrochemistry , pp. 2003
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  • 40
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    • Most often, metal salen complexes have been used in electrochemical processes wherein one of the substrates contains an alkyl, aryl, vinyl, allyl, or propargyl halide. This makes sense mechanistically, since the reduced form of nickel can oxidatively insert into the carbon-halogen bond. See ref 16c as well as (a) Condon, S.; Nedelec, J.-Y. Synthesis 2004, 18, 3070-3078.
    • (2004) Synthesis , vol.18 , pp. 3070-3078
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    • Halogenated Organic Compounds
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    • (a) Peters, D. G. Halogenated Organic Compounds. In Organic Electrochemistry, 4th ed.; Lund, H., Hammerich, O., Eds.; Dekker: New York: 2001; Chapter 8 and references therein.
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  • 52
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    • note
    • It is possible that the outcome has nothing to do with mechanistic detail shown in Scheme 5 but instead simply reflects that the additional 0.2 V presents a thermodynamic barrier that is too high to be overcome.
  • 56
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    • note
    • A reviewer has made the reasonable suggestion that the proposed equilibrium could be reformulated as a molecular orbital argument involving electron density redistribution. We agree but delay doing so until we obtain evidence to favor one viewpoint over another. In some respects, we have already incorporated aspects of a molecular orbital description by suggesting that the nature of the electrontransfer agent can vary in response to the electronic requirements of the substrate.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.