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Volumn 137, Issue 20, 2015, Pages 6476-6479

Ni-Catalyzed Divergent Cyclization/Carboxylation of Unactivated Primary and Secondary Alkyl Halides with CO2

Author keywords

[No Author keywords available]

Indexed keywords

CARBON DIOXIDE; CATALYSIS;

EID: 84930216584     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.5b03340     Document Type: Article
Times cited : (144)

References (80)
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    • Organonickel Chemistry
    • Lipshutz, B. H., Ed.; Wiley; Hoboken, NJ
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    • (2013) Organometallics in Synthesis , pp. 319-428
    • Montgomery, J.1
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    • See the Supporting Information for details
    • See the Supporting Information for details.
  • 49
    • 84930235140 scopus 로고    scopus 로고
    • Homodimerization accounts for the mass balance
    • Homodimerization accounts for the mass balance.
  • 54
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    • de Meijere, A.; Bräse, S.; Oestreich, M., Eds.; Wiley-VCH: Weinheim, Germany, Chapter 10
    • Marek, I.; Minko, Y. In Metal-Catalyzed Cross-Coupling Reactions and More; de Meijere, A.; Bräse, S.; Oestreich, M., Eds.; Wiley-VCH: Weinheim, Germany, 2014; Chapter 10, pp 763 - 874.
    • (2014) Metal-Catalyzed Cross-Coupling Reactions and More , pp. 763-874
    • Marek, I.1    Minko, Y.2
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    • 81355154663 scopus 로고    scopus 로고
    • Hu, X. Chem. Sci. 2011, 2, 1867
    • (2011) Chem. Sci. , vol.2 , pp. 1867
    • Hu, X.1
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    • 84930235142 scopus 로고    scopus 로고
    • note
    • Unfortunately, the use of tertiary alkyl halides resulted in recovered starting material or reduced products.
  • 73
    • 84930235143 scopus 로고    scopus 로고
    • note
    • We found that radical scavengers such as TEMPO, among others, did not inhibit the carboxylation of 1b. Interestingly, an otherwise similar experiment employing 4b as the substrate gave little conversion, if any, to 5b / 5b′. These results reinforce the notion that single-electron transfer (SET) processes come into play when dealing with secondary alkyl halides.
  • 76
    • 84930235144 scopus 로고    scopus 로고
    • note
    • Such a labeling pattern differs from previous work without pendant alkynes in the side chain (ref 4b). This observation is consistent with the ability of alkynes to act as noninnocent ancillary ligands. See ref 11d for an example of such behavior.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.