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Volumn 6, Issue 2, 2015, Pages 1115-1119

Cobalt co-catalysis for cross-electrophile coupling: Diarylmethanes from benzyl mesylates and aryl halides

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CATALYSTS; COBALT; FREE RADICAL REACTIONS; NICKEL;

EID: 84921633085     PISSN: 20416520     EISSN: 20416539     Source Type: Journal    
DOI: 10.1039/c4sc03106g     Document Type: Article
Times cited : (182)

References (66)
  • 12
    • 84921655261 scopus 로고    scopus 로고
    • note
    • For the use of Co(Pc) to activate alkyl halides for Cr-mediated coupling with aldehydes, see ref 9e and f.
  • 21
    • 84921655260 scopus 로고    scopus 로고
    • June
    • (https://scifinder.cas.org, June 2014)
    • (2014)
  • 44
    • 84921692868 scopus 로고    scopus 로고
    • note
    • 2Br; data from eMolecules database (eMolecules, Inc.), accessed via REAXYS (Elsevier, Inc.) on April 21, 2014.
  • 47
    • 84921674218 scopus 로고    scopus 로고
    • note
    • Co(Pc) reacted with benzyl mesylate to form benzyl radicals, quantitated as toluene (5, 4%) and bibenzyl (42%). See Table S1 in the ESI.†
  • 48
    • 84921655259 scopus 로고    scopus 로고
    • note
    • 2O, 5 mol% dtbbpy, and 2 equiv. Zn dust in DMA (0.25 M) at 60°C for 10 min. BnBr is consumed, most of the iodobenzene remains.
  • 49
    • 84921692867 scopus 로고    scopus 로고
    • note
    • 1a
  • 50
    • 84921655258 scopus 로고    scopus 로고
    • note
    • See ESI,† Scheme S1 and Chart S1-S10 for further selectivity and optimization details.
  • 54
    • 84921655257 scopus 로고    scopus 로고
    • note
    • We denote the same product made by a different set of substrates with a prime. For example, 3c and 3c′ are made from a different disconnection. 3a and 3a′ are made from differentbenzyl alcohol derivatives.
  • 57
    • 84921692866 scopus 로고    scopus 로고
    • note
    • See ref 13c and f for examples of coupling benzyl phosphate esters with arylmetal reagents.
  • 60
    • 84921692688 scopus 로고    scopus 로고
    • note
    • For examples of stereoselective or stereospecific coupling of benzylic substrates, see ref 13j, k and m- p, and the references in the following endnote.
  • 66
    • 84921637142 scopus 로고    scopus 로고
    • note
    • Further study is needed to better understand reactions of secondary benzylic chlorides. For these electrophiles, a cocatalyst may not be required. In preliminary studies, reactions run without added Co(Pc) provided similar results to reactions run with Co(Pc). Unlike reactions with vinyl bromides (ref. 16), reactions with bis(oxazoline) ligands provided low yields of racemic material.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.