Standard Article

Synthesis and Reactivity of Gold–Olefin Complexes

Organogold Compounds (2014)

  1. Chandrakanta Dash,
  2. H. V. Rasika Dias

Published Online: 26 JUN 2014

DOI: 10.1002/9780470682531.pat0816

Patai's Chemistry of Functional Groups

Patai's Chemistry of Functional Groups

How to Cite

Dash, C. and Rasika Dias, H. V. 2014. Synthesis and Reactivity of Gold–Olefin Complexes. Patai's Chemistry of Functional Groups. 1–40.

Author Information

  1. Department of Chemistry and Biochemistry, The University of Texas at Arlington, Arlington, Texas, USA

Publication History

  1. Published Online: 26 JUN 2014

Chemistry Terms

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Abstract

Gold catalysts have been used at an increasing frequency to facilitate a wide variety of organic transformations in synthetic organic chemistry. Among these, the functionalization of C[BOND]C multiple bonds (alkenes or alkynes) in the presence of gold catalysts are some of the most important strategies utilized for the construction of C[BOND]C, C[BOND]O and C[BOND]N bonds. A majority of these reactions are believed to proceed via gold-bound alkene (olefin) or alkyne intermediates. This chapter highlights some of the recent developments on the syntheses of gold-olefin complexes and their spectroscopic data and structural features. In addition, gold mediated inter- and intra-molecular nucleophilic addition reactions of nitrogen, oxygen or carbon nucleophiles to olefins are discussed. Reaction mechanisms of these nucleophilic addition reactions, in which gold[BOND]olefin adducts have been proposed as intermediates, are also presented.

Keywords:

  • alkenes;
  • gold;
  • homogeneous catalysis;
  • π-complexes;
  • nucleophilic additions;
  • reaction mechanisms;
  • transition metals

Featured Compounds

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  1. 1 - 64
Compound 45
Molecular Weight:555.4625
Molecular Formula:C25H28AuNO
InChIKey:AELIMFVLKMJSRV-UHFFFAOYSA-M
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Compound 5
Molecular Weight:846.034
Molecular Formula:C17H8AuBF18N6
InChIKey:FQENVUHNRMSQFR-UHFFFAOYSA-N
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Compound 15
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 18
Molecular Weight:1385.0442
Molecular Formula:C54H72Au2F8N4P2
InChIKey:WCYBHKMGKMJKBC-UHFFFAOYSA-N
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Compound 71
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 38
Molecular Weight:715.18
Molecular Formula:C21H30AuF6Sb
InChIKey:XBQJSIBKVQHOMX-UHFFFAOYSA-H
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Compound 51
Molecular Weight:484.286
Molecular Formula:C11H19AuF3O3S
InChIKey:NCCSEHJURANJFF-SUESZSCISA-M
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Compound 34
Molecular Weight:717.18
Molecular Formula:C18H37AuF6PSb
InChIKey:QWMMWCANNVNJDY-UHFFFAOYSA-H
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Compound 70
Molecular Weight:184.2338
Molecular Formula:C13H12O
InChIKey:RXWIAPFBYXLJHZ-UHFFFAOYSA-N
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Compound 33
Molecular Weight:1448.3
Molecular Formula:C38H64Au2F12P2Sb2
InChIKey:YJXGBPHFXGYJLD-UHFFFAOYSA-B
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Compound 7
Molecular Weight:868.159
Molecular Formula:C23H15AuBF15N6
InChIKey:RXNBAPJVQKTVTF-UHFFFAOYSA-N
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Compound 14
Molecular Weight:1264.96
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 47
Molecular Weight:886.38
Molecular Formula:C32H39AuF6NOSb
InChIKey:BRBBOFFNEIUKQX-UHFFFAOYSA-H
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Compound 30
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 22
Molecular Weight:905.46
Molecular Formula:C33H48AuF6N2Sb
InChIKey:WSARZJBVDSQXAE-UHFFFAOYSA-H
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Compound 13
Molecular Weight:110.1537
Molecular Formula:C7H10O
InChIKey:OHNNZOOGWXZCPZ-UHFFFAOYSA-N
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Compound 43
Molecular Weight:1231.567
Molecular Formula:C50H35AuBF18NO2
InChIKey:JOLIUTNVBGHMQV-UHFFFAOYSA-N
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Compound 6
Molecular Weight:870.328
Molecular Formula:C32H23AuBF9N6
InChIKey:QBPLVOJGDUNWCH-UHFFFAOYSA-N
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Compound 64
Molecular Weight:233.3062
Molecular Formula:C14H19NO2
InChIKey:DNVXNHGSWVUZQV-NYYWCZLTSA-N
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Compound 42
Molecular Weight:1191.503
Molecular Formula:C47H31AuBF18NO2
InChIKey:LEQKNNOLTHYOBU-UHFFFAOYSA-N
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Compound 9
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 8
Molecular Weight:921.091
Molecular Formula:C22H10AuCl4F14N3
InChIKey:RBOJWCUDVKVXCB-UHFFFAOYSA-N
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Compound 20
Molecular Weight:877.41
Molecular Formula:C31H44AuF6N2Sb
InChIKey:IONQYFYCOUEAMO-UHFFFAOYSA-H
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Compound 39
Molecular Weight:763.31
Molecular Formula:C24H42AuF6Sb
InChIKey:NMVUVCHIBISBTL-XGZQSMEOSA-H
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Compound 24
Molecular Weight:917.48
Molecular Formula:C34H48AuF6N2Sb
InChIKey:OBJAZDHIKQAZAZ-UHFFFAOYSA-H
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Compound 63
Molecular Weight:301.403
Molecular Formula:C17H19NO2S
InChIKey:YEKFSIAOSZCWGI-UHFFFAOYSA-N
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Compound 53
Molecular Weight:253.36
Molecular Formula:C13H19NO2S
InChIKey:DKYVVNLWACXMDW-UHFFFAOYSA-N
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Compound 31
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 32
Molecular Weight:1420.24
Molecular Formula:C36H60Au2F12P2Sb2
InChIKey:SRYSFVSQEYHUDA-UHFFFAOYSA-B
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Compound 4
Molecular Weight:1791.759
Molecular Formula:C56H44Au4Cl2N2P4S2
InChIKey:ZNEXSJFYCVBCSO-VVCBSBRZSA-J
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Compound 69
Molecular Weight:184.2338
Molecular Formula:C13H12O
InChIKey:JHEKBCPEJKZQIY-UHFFFAOYSA-N
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Compound 49
Molecular Weight:395.2501
Molecular Formula:C14H16AuN
InChIKey:ZFKVUSXHYQQSIJ-UHFFFAOYSA-N
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Compound 27
Molecular Weight:939.48
Molecular Formula:C36H46AuF6N2Sb
InChIKey:HSXBHBQLEBPUHJ-UHFFFAOYSA-H
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Compound 46
Molecular Weight:573.908
Molecular Formula:C25H27AuClN
InChIKey:KBDNOWFQDUBNRR-UHFFFAOYSA-M
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Compound 59
Molecular Weight:246.348
Molecular Formula:C15H22N2O
InChIKey:VVTHGTAMJTYWMR-QWHCGFSZSA-N
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Compound 48
Molecular Weight:1289.646
Molecular Formula:C53H41AuBF18NO3
InChIKey:IDTMEPDEKPHLKO-UHFFFAOYSA-N
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Compound 60
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 84
Molecular Weight:186.2051
Molecular Formula:C9H14O4
InChIKey:YPTLFOZCUOHVFO-VOTSOKGWSA-N
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Compound 19
Molecular Weight:790.535
Molecular Formula:C36H46AuBF4N2
InChIKey:HNTBVYDYBHSJME-UHFFFAOYSA-N
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Compound 52
Molecular Weight:1198.427
Molecular Formula:C42H30AuBF24
InChIKey:JASYDNLWRYACJW-KJWGIZLLSA-N
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Compound 35
Molecular Weight:841.32
Molecular Formula:C28H41AuF6PSb
InChIKey:FTRZBQHCOSTPSL-UHFFFAOYSA-H
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Compound 61
Molecular Weight:144.213
Molecular Formula:C11H12
InChIKey:VQBRSCDCSOKQHR-UHFFFAOYSA-N
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Compound 37
Molecular Weight:516.88
Molecular Formula:C6H12AuF6Sb
InChIKey:PHXHRKBWLWIWHQ-UHFFFAOYSA-H
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Compound 72
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 17
Molecular Weight:822.6573
Molecular Formula:C34H44AuF6N2P
InChIKey:QLZURPOVOSYRJJ-UHFFFAOYSA-N
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Compound 25
Molecular Weight:877.41
Molecular Formula:C31H44AuF6N2Sb
InChIKey:RXHIIEYCANAQSO-OTAHFQHPSA-H
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Compound 50
Molecular Weight:545.327
Molecular Formula:C15H17AuF3NO3S
InChIKey:AGZRYKHVSCIAJX-UHFFFAOYSA-M
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Compound 21
Molecular Weight:915.46
Molecular Formula:C34H46AuF6N2Sb
InChIKey:FVJOTYKZVFODNR-UHFFFAOYSA-H
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Compound 41
Molecular Weight:651.4706
Molecular Formula:C27H27AuF3NO2
InChIKey:RPQNVJJQDITRCI-UHFFFAOYSA-M
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Compound 28
Molecular Weight:1601.8028
Molecular Formula:C47H51AlAuF36NO4
InChIKey:LPXWQDNSYBRRPV-PEONKWDUSA-N
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Compound 23
Molecular Weight:891.44
Molecular Formula:C32H46AuF6N2Sb
InChIKey:HCWXBLRJSIDYSR-UHFFFAOYSA-H
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Compound 36
Molecular Weight:845.26
Molecular Formula:C26H37AuF6O2PSb
InChIKey:MMEHZKOSKJJKOO-UHFFFAOYSA-H
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Compound 26
Molecular Weight:905.46
Molecular Formula:C33H48AuF6N2Sb
InChIKey:SKKLAGSEVBNGQD-UHFFFAOYSA-H
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Compound 44
Molecular Weight:1257.605
Molecular Formula:C52H37AuBF18NO2
InChIKey:RJQGKQSILUHDDH-UHFFFAOYSA-N
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Compound 62
Molecular Weight:301.403
Molecular Formula:C17H19NO2S
InChIKey:VBDKKVVDQRGJQD-OQLLNIDSSA-N
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Compound 85
Molecular Weight:262.301
Molecular Formula:C15H18O4
InChIKey:KYFSKKXDQHJWKR-RAXLEYEMSA-N
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Compound 54
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 40
Molecular Weight:649.08
Molecular Formula:C16H24AuF6Sb
InChIKey:CSJIZEHUUVOFRY-SXGOCSEPSA-H
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Compound 55
Molecular Weight:433.602
Molecular Formula:C27H29NO2S
InChIKey:Not Available
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Compound 56
Molecular Weight:433.602
Molecular Formula:C27H29NO2S
InChIKey:Not Available
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Compound 57
Molecular Weight:433.602
Molecular Formula:C27H29NO2S
InChIKey:Not Available
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Compound 12
Molecular Weight:622.295
Molecular Formula:C18H20AuF6N2OP
InChIKey:QNJQTWAVIFJREX-UHFFFAOYSA-N
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Compound 80
Molecular Weight:231.2903
Molecular Formula:C14H17NO2
InChIKey:ASCCCFQJBMQFLZ-GWCFXTLKSA-N
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Compound 16
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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  1. 1 - 64