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Keywords:

  • alkenes;
  • alkynes;
  • ethers;
  • gold;
  • heterocycles

Abstract

The gold-catalyzed conversion of allyl-(ortho-alkynylphenyl)methyl ethers was investigated, and allylated isochromenes were obtained. An optimization of the catalysis conditions with respect to different phosphane and carbene ligands on gold, different counterions, and different solvents was conducted. Subsequently, the scope and limitations of this reaction were investigated with 21 substrates. The mechanistic studies show an allylic inversion, as supported by NMR data and an X-ray crystal structure analysis, as well as an intermolecular reaction, as determined by crossover experiments. There is no competition of protodeauration even in the presence of water. All these observations differ from other related conversions and clearly indicate product formation by a [3,3]sigmatropic rearrangement in the step forming the new C[BOND]C bond.

Featured Compounds

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  1. 1 - 72
Compound 1
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 8
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 9
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 15
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 16
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 17
Molecular Weight:185.018
Molecular Formula:C7H5BrO
InChIKey:Not Available
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Compound 18a
Molecular Weight:186.2497
Molecular Formula:C13H14O
InChIKey:FETDVTPMFRPTLM-UHFFFAOYSA-N
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Compound 18b
Molecular Weight:206.2393
Molecular Formula:C15H10O
InChIKey:Not Available
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Compound 20a
Molecular Weight:324.415
Molecular Formula:C24H20O
InChIKey:SGNDZLQIOUUBFP-NTEUORMPSA-N
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Compound 20b
Molecular Weight:304.4254
Molecular Formula:C22H24O
InChIKey:KZPLYWBZQOOJCD-SDNWHVSQSA-N
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Compound 19a
Molecular Weight:188.2655
Molecular Formula:C13H16O
InChIKey:FIEFOXBAHCMYMN-UHFFFAOYSA-N
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Compound 19b
Molecular Weight:208.2552
Molecular Formula:C15H12O
InChIKey:JLZVTPSCFFBAKH-UHFFFAOYSA-N
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Compound K1
Molecular Weight:329.578
Molecular Formula:C6H11AuClN
InChIKey:XOLTVAAYFWIOAJ-UHFFFAOYSA-M
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Compound 21a
Molecular Weight:324.415
Molecular Formula:C24H20O
InChIKey:ILPCTHKISNHERH-UHFFFAOYSA-N
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Compound 21b
Molecular Weight:304.4254
Molecular Formula:C22H24O
InChIKey:BXMYSPKAUGJBKN-UHFFFAOYSA-N
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Compound 22
Molecular Weight:208.2552
Molecular Formula:C15H12O
InChIKey:WIWSGSFVLIGZRH-UHFFFAOYSA-N
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Compound K2
Molecular Weight:388.688
Molecular Formula:C9H20AuClN2
InChIKey:HQONQYYKSTZXJV-UHFFFAOYSA-M
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Compound K3
Molecular Weight:879.341
Molecular Formula:C42H63AuClO3P
InChIKey:GCWCLHMEYZKZRO-UHFFFAOYSA-M
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Compound K4
Molecular Weight:590.96
Molecular Formula:C24H39AuClP
InChIKey:DPVLFPAEEHRXSM-UHFFFAOYSA-M
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Compound K5
Molecular Weight:494.705
Molecular Formula:C18H15AuClP
InChIKey:Not Available
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Compound K6
Molecular Weight:621.008
Molecular Formula:C27H36AuClN2
InChIKey:UAUDQGGWKSQITI-UHFFFAOYSA-M
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Compound K7
Molecular Weight:887.641
Molecular Formula:C28H35AuF6NO6PS2
InChIKey:DCWMCSDFBBTUCM-UHFFFAOYSA-N
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Compound K8
Molecular Weight:303.326
Molecular Formula:AuCl3
InChIKey:RJHLTVSLYWWTEF-UHFFFAOYSA-K
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Compound 23
Molecular Weight:234.0344
Molecular Formula:C7H7IO
InChIKey:WZCXOBMFBKSSFA-UHFFFAOYSA-N
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Compound 20
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 20c
Molecular Weight:228.3294
Molecular Formula:C16H20O
InChIKey:ZJDGIPGPVIOSOK-UHFFFAOYSA-N
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Compound 20d
Molecular Weight:262.3456
Molecular Formula:C19H18O
InChIKey:KENOODORDIDHPO-NSCUHMNNSA-N
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Compound 20e
Molecular Weight:276.3722
Molecular Formula:C20H20O
InChIKey:NQHPURHYJCWDKX-UHFFFAOYSA-N
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Compound 20f
Molecular Weight:288.3829
Molecular Formula:C21H20O
InChIKey:WJSQTDACEAIPNJ-UHFFFAOYSA-N
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Compound 20g
Molecular Weight:354.441
Molecular Formula:C25H22O2
InChIKey:DSYMTZGAZKTRJH-JXMROGBWSA-N
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Compound 20h
Molecular Weight:320.5002
Molecular Formula:C21H24OSi
InChIKey:IGYNHELBWMNDEU-FMIVXFBMSA-N
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Compound 20i
Molecular Weight:248.319
Molecular Formula:C18H16O
InChIKey:NHNWDJKFZOBMAV-DHZHZOJOSA-N
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Compound 20j
Molecular Weight:306.3551
Molecular Formula:C20H18O3
InChIKey:AAKYRMXMDCDDHV-JXMROGBWSA-N
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Compound 20k
Molecular Weight:288.3829
Molecular Formula:C21H20O
InChIKey:MYMYLSCASJNHSC-DHZHZOJOSA-N
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Compound 20l
Molecular Weight:354.441
Molecular Formula:C25H22O2
InChIKey:ZIXPRQGSGISMMC-UKTHLTGXSA-N
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Compound 20m
Molecular Weight:454.6753
Molecular Formula:C30H34O2Si
InChIKey:YPUPOXLIWYOSJM-DTQAZKPQSA-N
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Compound 20n
Molecular Weight:468.7018
Molecular Formula:C31H36O2Si
InChIKey:ICFHMSJUVMGCPA-DTQAZKPQSA-N
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Compound 20o
Molecular Weight:392.6059
Molecular Formula:C25H32O2Si
InChIKey:ZXSKPCWDXCFLRY-RVDMUPIBSA-N
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Compound 20p
Molecular Weight:406.6325
Molecular Formula:C26H34O2Si
InChIKey:LULDICKSDSWIDF-DTQAZKPQSA-N
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Compound 20q
Molecular Weight:420.659
Molecular Formula:C27H36O2Si
InChIKey:CYSWGNWHEJBPPP-SAPNQHFASA-N
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Compound 20r
Molecular Weight:434.6856
Molecular Formula:C28H38O2Si
InChIKey:KGDKJFXDQPRHES-OBGWFSINSA-N
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Compound 20s
Molecular Weight:298.3777
Molecular Formula:C22H18O
InChIKey:AHJGQLQOLUOBFM-UHFFFAOYSA-N
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Compound 20t
Molecular Weight:278.3881
Molecular Formula:C20H22O
InChIKey:NJJVWIVEEAAOLS-UHFFFAOYSA-N
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Compound 20u
Molecular Weight:294.4629
Molecular Formula:C19H22OSi
InChIKey:ZMDZTJPEOXFECD-UHFFFAOYSA-N
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Compound 21
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 21c
Molecular Weight:228.3294
Molecular Formula:C16H20O
InChIKey:DEVCTJMQUYAXFS-UHFFFAOYSA-N
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Compound 21d
Molecular Weight:262.3456
Molecular Formula:C19H18O
InChIKey:BCPIZSNSEDEZBH-UHFFFAOYSA-N
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Compound 21e
Molecular Weight:276.3722
Molecular Formula:C20H20O
InChIKey:VDOPSXCLMOYCKL-UHFFFAOYSA-N
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Compound 21f
Molecular Weight:288.3829
Molecular Formula:C21H20O
InChIKey:SWHQPICYPVJXDY-UHFFFAOYSA-N
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Compound 21g
Molecular Weight:354.441
Molecular Formula:C25H22O2
InChIKey:WQLKEUOECPJUMO-UHFFFAOYSA-N
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Compound 21i
Molecular Weight:248.319
Molecular Formula:C18H16O
InChIKey:MCIOMAXCDRSPFP-UHFFFAOYSA-N
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Compound 21j
Molecular Weight:306.3551
Molecular Formula:C20H18O3
InChIKey:LRUHKKWMMUQJHU-KEZACMBGSA-N
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Compound 21k
Molecular Weight:288.3829
Molecular Formula:C21H20O
InChIKey:QQOCMMYGGAKHNF-UHFFFAOYSA-N
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Compound 21l
Molecular Weight:354.441
Molecular Formula:C25H22O2
InChIKey:BRHYKLDKYINXLJ-UHFFFAOYSA-N
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Compound 21m
Molecular Weight:454.6753
Molecular Formula:C30H34O2Si
InChIKey:BEXCHWOWEXMTOZ-UHFFFAOYSA-N
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Compound 21n
Molecular Weight:468.7018
Molecular Formula:C31H36O2Si
InChIKey:NEEPYTCWUYPPGV-UHFFFAOYSA-N
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Compound 21o
Molecular Weight:392.6059
Molecular Formula:C25H32O2Si
InChIKey:MLYCMMVZGHYDGO-UHFFFAOYSA-N
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Compound 21p
Molecular Weight:406.6325
Molecular Formula:C26H34O2Si
InChIKey:WKDFYOUQPIWUEK-UHFFFAOYSA-N
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Compound 21q
Molecular Weight:420.659
Molecular Formula:C27H36O2Si
InChIKey:FMLFTYWSAWHQSH-UHFFFAOYSA-N
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Compound 21r
Molecular Weight:434.6856
Molecular Formula:C28H38O2Si
InChIKey:OIXSXYRAGQFGQZ-UHFFFAOYSA-N
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Compound 20v
Molecular Weight:256.3826
Molecular Formula:C18H24O
InChIKey:MQDCWELHOKQSJU-GQCTYLIASA-N
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Compound 21v
Molecular Weight:256.3826
Molecular Formula:C18H24O
InChIKey:KMNIQAWNUHRERI-GQCTYLIASA-N
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Compound 21w
Molecular Weight:242.356
Molecular Formula:C17H22O
InChIKey:ONFRVDIYAICBKN-UHFFFAOYSA-N
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Compound 21x
Molecular Weight:242.356
Molecular Formula:C17H22O
InChIKey:LAUBTMHOEVJABP-HWKANZROSA-N
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Compound 25
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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  1. 1 - 72