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Volumn 55, Issue 8, 2016, Pages 2810-2814

Nickel-Catalyzed Activation of Acyl C-O Bonds of Methyl Esters

Author keywords

C O activation; density functional calculations; methyl esters; nickel catalysis; oxidative addition

Indexed keywords

CATALYSIS; CHEMICAL ACTIVATION; DENSITY FUNCTIONAL THEORY; ESTERS; NICKEL; REACTION KINETICS; THERMODYNAMICS;

EID: 84956685887     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201511486     Document Type: Article
Times cited : (144)

References (50)
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    • As shown in Figure 6, theory predicts that substrate 5 should prove most suitable.
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    • note
    • On gram scale, this coupling could be performed with 2.5 mol % of Ni to give amide 7 in 50 % yield; see the Supporting Information for details.
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    • note
    • The use of other ligands (e.g., mono- and bidentate phosphines, bidentate pyridyl, pybox, and many other N-heterocyclic carbenes) in place of SIPr also led to no reaction or low conversions. IPr, however, can be used in place of SIPr to give comparable yields of products.
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    • note
    • The mass balance in most reactions is unreacted starting material.
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    • note
    • The favorable reactivity seen with π-extended systems may be related to pre-complexation of the nickel catalyst, as well as to the thermodynamic factors discussed here.
  • 39
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    • note
    • The non-catalyzed reaction of anilines with ester 5 is sluggish and not observed under our reaction conditions.
  • 44
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    • note
    • The variation between the calculated thermoneutral reaction free energy and the observed yields may partially be attributed to differences between the actual experimental conditions and those used for the DFT calculations.
  • 45
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    • note
    • -1.
  • 47
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    • note
    • For further discussion, see the Supporting Information.
  • 48
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    • note
    • Distortion of bond lengths was also examined, but found to be insignificant in all cases.
  • 49
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    • note
    • 3 stability; rather, electron donation from the amide nitrogen atom is the primary stabilizing factor.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.