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Keywords:

  • C[BOND]C coupling;
  • copper;
  • domino reactions;
  • heterocycles;
  • methylene

Abstract

Active methylene compounds are a major class of reaction partners for C[BOND]C bond formation with sp2 C[BOND]X (X=halide) fragments. As one of the most-classical versions of the Ullmann-type coupling reaction, activated-methylene-based C[BOND]C coupling reactions have been efficiently employed in a large number of syntheses. Although this type of reaction has long relied on noble-metal catalysis, the renaissance of copper catalysis at the end of last century has led to dramatic developments in Ullmann C[BOND]C coupling reactions. Owing to its low cost, abundance, as well as excellent catalytic activity, the exceptional atom economy of copper catalysis is gaining widespread attention in various organic synthesis. This review summarizes the advances in copper-catalyzed intermolecular and intramolecular C[BOND]C coupling reactions that use activated methylene species as well as in tandem reactions that are initiated by this transformation.

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Featured Compounds

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  1. 1 - 69
Compound 1
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound L1
Molecular Weight:170.2072
Molecular Formula:C12H10O
InChIKey:LLEMOWNGBBNAJR-UHFFFAOYSA-N
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Compound L2
Molecular Weight:292.3782
Molecular Formula:C18H20N4
InChIKey:VYIMTYRAXWNXFU-BGSCIDCASA-N
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Compound L3
Molecular Weight:115.1305
Molecular Formula:C5H9NO2
InChIKey:ONIBWKKTOPOVIA-BYPYZUCNSA-N
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Compound L4
Molecular Weight:131.1299
Molecular Formula:C5H9NO3
InChIKey:Not Available
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Compound L5
Molecular Weight:123.1094
Molecular Formula:C6H5NO2
InChIKey:SIOXPEMLGUPBBT-UHFFFAOYSA-N
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Compound L6
Molecular Weight:294.3941
Molecular Formula:C18H22N4
InChIKey:GAZUJKJJBRIPLV-MXWIWYRXSA-N
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Compound L7
Molecular Weight:174.2025
Molecular Formula:C9H10N4
InChIKey:YBHNBQWIYUHSSX-UHFFFAOYSA-N
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Compound L8
Molecular Weight:88.1515
Molecular Formula:C4H12N2
InChIKey:Not Available
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Compound L9
Molecular Weight:236.3116
Molecular Formula:C16H16N2
InChIKey:NPAXPTHCUCUHPT-UHFFFAOYSA-N
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Compound L10
Molecular Weight:286.324
Molecular Formula:C20H14O2
InChIKey:PPTXVXKCQZKFBN-UHFFFAOYSA-N
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Compound L11
Molecular Weight:129.157
Molecular Formula:C6H11NO2
InChIKey:HXEACLLIILLPRG-UHFFFAOYSA-N
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Compound L12
Molecular Weight:268.3104
Molecular Formula:C16H16N2O2
InChIKey:HRLCXCDIUZLSCB-UHFFFAOYSA-N
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Compound 3
Molecular Weight:163.1733
Molecular Formula:C9H9NO2
InChIKey:XCHBYBKNFIOSBB-SECBINFHSA-N
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Compound 2
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 4
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 5
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 6
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 7
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 10
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 11
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 12
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 13
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 14
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 15
Molecular Weight:412.114
Molecular Formula:C14H20Br2O4
InChIKey:AEURNHJWCSJFTF-UHFFFAOYSA-N
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Compound 16
Molecular Weight:331.202
Molecular Formula:C14H19BrO4
InChIKey:JGOCCKRXARJPME-UHFFFAOYSA-N
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Compound 17
Molecular Weight:263.128
Molecular Formula:C10H15BrO3
InChIKey:ORWCFOKRKIFPLY-UHFFFAOYSA-N
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Compound 18
Molecular Weight:182.2164
Molecular Formula:C10H14O3
InChIKey:UGUGRZCXUNCCSG-UHFFFAOYSA-N
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Compound 19
Molecular Weight:182.2164
Molecular Formula:C10H14O3
InChIKey:ZDAZBEHAIOYSPW-UHFFFAOYSA-N
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Compound 20
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 21
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 22
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 23
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 25
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 24
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 28
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 29
Molecular Weight:487.697
Molecular Formula:C6H2Br2I2
InChIKey:IVKPEQAIHJWGGT-UHFFFAOYSA-N
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Compound 30
Molecular Weight:330.3319
Molecular Formula:C18H18O6
InChIKey:CFKGXXNWAGBBFU-UHFFFAOYSA-N
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Compound 31
Molecular Weight:283.118
Molecular Formula:C12H11BrO3
InChIKey:JXEBGYGCFSMZMV-UHFFFAOYSA-N
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Compound 32
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 33
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 34
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 35
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 39
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 40
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 43
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 41
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 42
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 44
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 45
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 46
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 49
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 50
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 51
Molecular Weight:308.3312
Molecular Formula:C18H16N2O3
InChIKey:VFZWPZXEIMBNHN-UHFFFAOYSA-N
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Compound 52
Molecular Weight:276.129
Molecular Formula:C13H10BrNO
InChIKey:USYBDUIHFMIQCP-UHFFFAOYSA-N
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Compound 53
Molecular Weight:195.2167
Molecular Formula:C13H9NO
InChIKey:FIISKTXZUZBTRC-UHFFFAOYSA-N
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Compound 54
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 56
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 57
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 58
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 59
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 60
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 61
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 62
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 65
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 66
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 70
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 71
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 74
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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