Standard Article

Palladacycles in Catalysis

Part 1. Homogeneous Catalysis

  1. Jairton Dupont,
  2. Fabricio R. Flores

Published Online: 15 JUL 2010

DOI: 10.1002/9783527628698.hgc010

Handbook of Green Chemistry

Handbook of Green Chemistry

How to Cite

Dupont, J. and Flores, F. R. 2010. Palladacycles in Catalysis. Handbook of Green Chemistry. 1:10:319–342.

Author Information

  1. UFRGS, Institute of Chemistry, Laboratory of Molecular Catalysis avenue Bento Goncalves, Porto Alegre, France

Publication History

  1. Published Online: 15 JUL 2010

Chemistry Terms

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Abstract

Palladium compounds containing a Pd-C that are stabilized intramolecularly by at least one two-electron donor group have numerous applications as pre-catalysts. In particular, these compounds denominated palladacycles possess very attractive properties such as high thermal stability and low air sensitivity and they are ease to handle. These compounds are very active catalyst precursors in Heck coupling, Suzuki coupling, Buchwald–Hartwig amination and related coupling reactions under mild conditions, for instance at room temperature or in water. However, palladacycles serve as precursors to highly active palladium(0) species consist of soluble clusters or colloids, often stabilized by quaternary ammonium salts in highly dilute solutions or highly active low-coordinate complexes of electron-rich phosphines or carbenes. Moreover, chiral palladacycles are very important catalysts for enantioselective allylic rearrangements, allylic additions and aldol chemistry, since they act as Pd(II) Lewis acids and no redox process occurs

Keywords:

  • homogeneous catalysis;
  • palladacycles;
  • coupling reactions;
  • aldol reactions;
  • allylic rearrangements

Featured Compounds

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  1. 1 - 49
Compound 1
Molecular Weight:937.64
Molecular Formula:C46H46O4P2Pd2
InChIKey:YRGPDGDJUOTURS-UHFFFAOYSA-L
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Compound 2
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 3
Molecular Weight:670.4
Molecular Formula:C24H34Cl2Pd2S2
InChIKey:YCEZVNKOCKIJAN-UHFFFAOYSA-L
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Compound 4
Molecular Weight:673.11
Molecular Formula:C22H26Cl4N2Pd2
InChIKey:ZPKHIYQTICDKHU-UHFFFAOYSA-L
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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:483.26
Molecular Formula:C18H31ClO2P2Pd
InChIKey:IDKFGIIIAABDFH-UHFFFAOYSA-M
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Compound 8
Molecular Weight:333.17
Molecular Formula:C12H19ClN2Pd
InChIKey:VHCTXQNIHPIABV-UHFFFAOYSA-M
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Compound 9
Molecular Weight:552.14
Molecular Formula:C18H24Cl2N2Pd2
InChIKey:DSRDIGYUGAOPJI-UHFFFAOYSA-L
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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:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 16
Molecular Weight:634.06
Molecular Formula:C29H45F3NO2PPd
InChIKey:IADZMQWQCHTGAE-UHFFFAOYSA-M
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Compound 17
Molecular Weight:793.69
Molecular Formula:C39H57ClO4P2Pd
InChIKey:IJMPHDSJQQHRIO-UHFFFAOYSA-M
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Compound 18
Molecular Weight:1245.7
Molecular Formula:C60H74Fe2O4P2Pd2
InChIKey:BFZSJVYKTCWEIJ-UHFFFAOYSA-L
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Compound 19
Molecular Weight:1778.6
Molecular Formula:C78H70N2O6P2Pd2Re2
InChIKey:BFRPQOSDMIZAFS-UHFFFAOYSA-L
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Compound 20
Molecular Weight:925.72
Molecular Formula:C44H58O4P2Pd2
InChIKey:FPWCUHUDFSZVGD-UHFFFAOYSA-L
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Compound L
Molecular Weight:380.4612
Molecular Formula:C27H25P
InChIKey:KQJCSAMBPMEBLR-UHFFFAOYSA-N
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Compound 21
Molecular Weight:490.38
Molecular Formula:C23H30ClN3Pd
InChIKey:CDKRRMBWCHZPLY-UHFFFAOYSA-M
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Compound 22
Molecular Weight:745.09
Molecular Formula:C26H18Cl4N2O2Pd2
InChIKey:VBXAHLDVCPCAEO-ZYTCZVDRSA-L
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Compound 23
Molecular Weight:868.54
Molecular Formula:C28H28Cl2N2O4Pd2S4
InChIKey:LGBUAHDYOOGPEG-UHFFFAOYSA-L
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Compound 24
Molecular Weight:698.97
Molecular Formula:C35H24F3N2O2PPd
InChIKey:MLCOORPGQAZRAN-UHFFFAOYSA-M
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Compound 25
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 26
Molecular Weight:419.2
Molecular Formula:C14H22ClN4PPd
InChIKey:KJIQUHDFYBUKNU-UHFFFAOYSA-M
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Compound 27
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:584.06
Molecular Formula:C16H16Cl2N2O4Pd2
InChIKey:LZIRABOKYWYVSI-FIOBSCOQSA-L
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Compound 30
Molecular Weight:Not Available
Molecular Formula:(C2H4O)nC18H18Cl2N2O4Pd2
InChIKey:Not Available
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Compound 31
Molecular Weight:880.53
Molecular Formula:C42H37O4P2Pd2
InChIKey:Not Available
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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 36
Molecular Weight:580.2
Molecular Formula:C20H28Cl2N2Pd2
InChIKey:XCTXLCNHZNUSDD-GEEYZVESSA-L
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Compound 37
Molecular Weight:780.43
Molecular Formula:C36H36Cl2N2Pd2
InChIKey:MNBUTMWYIWARAY-CHKLPSMSSA-L
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Compound 38
Molecular Weight:724.09
Molecular Formula:C42H35OP2Pd
InChIKey:NRLVHRFEXQGQMJ-UHFFFAOYSA-N
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Compound 39
Molecular Weight:732.94
Molecular Formula:C31H23F3O5P2PdS
InChIKey:UANQBTWUTCSTAI-UHFFFAOYSA-M
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Compound 40
Molecular Weight:1027.08
Molecular Formula:C50H35IO6P2Pd
InChIKey:KRZQZZZBQYBYBI-UHFFFAOYSA-M
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Compound 41
Molecular Weight:643.43
Molecular Formula:C34H31ClP2Pd
InChIKey:FKNQZTJIJDWVJV-QLBXQKMFSA-M
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Compound 42
Molecular Weight:532
Molecular Formula:C26H37N2O3Pd
InChIKey:YEQIOUODQXUDEW-KUSCCAPHSA-N
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Compound 43
Molecular Weight:707.42
Molecular Formula:C28H34N2O6Pd2
InChIKey:IBHUPFKVUDNYMZ-KGFKVAEWSA-L
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Compound 44
Molecular Weight:639.3
Molecular Formula:C26H22N2O4Pd2
InChIKey:QWXKDFIUDYQKLU-UHFFFAOYSA-L
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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 47
Molecular Weight:377.62
Molecular Formula:C12H19BrN2Pd
InChIKey:QQJFCMMEWYAFGZ-UHFFFAOYSA-M
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Compound 48
Molecular Weight:557.14
Molecular Formula:C20H17ClPdSe2
InChIKey:UPTIBUSNQPQCIY-UHFFFAOYSA-M
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  1. 1 - 49