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Ethylene Glycol: A Powerful Catalyst-Free Medium for C[BOND]C Bond-Forming Reactions

  1. Yun-Lin Liu1,
  2. Xing-Ping Zeng1,
  3. Prof. Dr. Jian Zhou1,2,*

Article first published online: 4 JUN 2012

DOI: 10.1002/asia.201200289

Issue

Chemistry – An Asian Journal

Chemistry – An Asian Journal

Volume 7, Issue 8, pages 1759–1763, August 2012

Additional Information

How to Cite

Liu, Y.-L., Zeng, X.-P. and Zhou, J. (2012), Ethylene Glycol: A Powerful Catalyst-Free Medium for C[BOND]C Bond-Forming Reactions. Chem. Asian J., 7: 1759–1763. doi: 10.1002/asia.201200289

Author Information

  1. 1

    Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663N, Zhongshan Road, Shanghai 200062 (China), Fax: (+86) 21-62234560

  2. 2

    State Key Laboratory of Elemento-organic Chemistry, Nankai University, Tianjin 300071 (P. R. China)

*Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663N, Zhongshan Road, Shanghai 200062 (China), Fax: (+86) 21-62234560

Publication History

  1. Issue published online: 12 JUL 2012
  2. Article first published online: 4 JUN 2012
  3. Manuscript Received: 3 APR 2012

Funded by

  • NSFC. Grant Numbers: 20902025, 21172075
  • Innovation Program of SMEC. Grant Number: 12ZZ046
  • Shanghai Pujiang Program. Grant Number: 10J1403100
  • Fundamental Research Funds for the Central Universities. Grant Number: ECNU 11043
  • 973 program. Grant Number: 2011CB808600

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Keywords:

  • C[BOND]C coupling;
  • ethylene glycol;
  • homogeneous reactions;
  • solvent effects;
  • Strecker reaction
Thumbnail image of graphical abstract

A good EG: Ethylene glycol (EG) is a catalyst-free medium that can promote the highly efficient Strecker reaction of α-CF2H or α-CF3 ketoimines and TMSCN. EG was used in several reactions, including the catalyst-free Morita–Baylis–Hillman reaction.

Featured Compounds

Compound 1
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 1a
Molecular Weight:279.2571
Molecular Formula:C15H12F3NO
InChIKey:PQGWMIMWOGQFEQ-RGEXLXHISA-N
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Compound 1x
Molecular Weight:293.2837
Molecular Formula:C16H14F3NO
InChIKey:DCPVUKPNQWOQLH-HKWRFOASSA-N
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Compound 2
Molecular Weight:99.2065
Molecular Formula:C4H9NSi
InChIKey:Not Available
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Compound 3a
Molecular Weight:306.2824
Molecular Formula:C16H13F3N2O
InChIKey:SCNKXMLRCGDSDV-UHFFFAOYSA-N
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Compound 3x
Molecular Weight:320.309
Molecular Formula:C17H15F3N2O
InChIKey:STTFBSOTMSIAOD-UHFFFAOYSA-N
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Compound 4
Molecular Weight:500.305
Molecular Formula:C17H8F12N2S
InChIKey:RWXWQJYJWJNJNW-UHFFFAOYSA-N
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Compound 11
Molecular Weight:123.1525
Molecular Formula:C7H9NO
InChIKey:BHAAPTBBJKJZER-UHFFFAOYSA-N
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Compound 1r
Molecular Weight:285.3047
Molecular Formula:C15H18F3NO
InChIKey:GHCBJOKNYXEZDM-RGEXLXHISA-N
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Compound 3r
Molecular Weight:312.3301
Molecular Formula:C16H19F3N2O
InChIKey:OGTQIAMYGZGZDM-UHFFFAOYSA-N
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Compound 1b
Molecular Weight:309.2831
Molecular Formula:C16H14F3NO2
InChIKey:YEIXMQOSRZFPJQ-HKWRFOASSA-N
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Compound 1c
Molecular Weight:309.2831
Molecular Formula:C16H14F3NO2
InChIKey:PXZUOXSQFVDKCI-HKWRFOASSA-N
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Compound 1d
Molecular Weight:313.702
Molecular Formula:C15H11ClF3NO
InChIKey:CXVHOUACTNFTLA-ZHZULCJRSA-N
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Compound 1e
Molecular Weight:358.153
Molecular Formula:C15H11BrF3NO
InChIKey:MAOAEFGLGQZRPB-ZHZULCJRSA-N
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Compound 1f
Molecular Weight:297.2476
Molecular Formula:C15H11F4NO
InChIKey:DEEHMLWGGYQOHQ-ZHZULCJRSA-N
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Compound 1g
Molecular Weight:285.285
Molecular Formula:C13H10F3NOS
InChIKey:USMGPSBEYXMJRV-ATVHPVEESA-N
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Compound 1h
Molecular Weight:217.1877
Molecular Formula:C10H10F3NO
InChIKey:JWYVMWMPDGALGS-AUWJEWJLSA-N
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Compound 1i
Molecular Weight:307.3102
Molecular Formula:C17H16F3NO
InChIKey:QLXPGGCFHGPSAC-PGMHBOJBSA-N
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Compound 1j
Molecular Weight:261.2666
Molecular Formula:C15H13F2NO
InChIKey:GIEUMOICSKMWQH-JXAWBTAJSA-N
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Compound 1k
Molecular Weight:275.2932
Molecular Formula:C16H15F2NO
InChIKey:LXMWXFHSFZDKAE-CYVLTUHYSA-N
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Compound 1l
Molecular Weight:275.2932
Molecular Formula:C16H15F2NO
InChIKey:DLDHFJOSODUGBI-CYVLTUHYSA-N
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Compound 1m
Molecular Weight:295.712
Molecular Formula:C15H12ClF2NO
InChIKey:QSUKTPCPCFDMFW-RGEXLXHISA-N
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Compound 1n
Molecular Weight:291.2926
Molecular Formula:C16H15F2NO2
InChIKey:WAQMUXFABUKQNN-CYVLTUHYSA-N
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Compound 1o
Molecular Weight:225.2857
Molecular Formula:C15H15NO
InChIKey:WATIYJMFKFSKGZ-FOWTUZBSSA-N
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Compound 1p
Molecular Weight:287.3551
Molecular Formula:C20H17NO
InChIKey:AOYNFODYHKOEKG-UHFFFAOYSA-N
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Compound 3
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 3b
Molecular Weight:336.3084
Molecular Formula:C17H15F3N2O2
InChIKey:YFGILTAYBCEMRF-UHFFFAOYSA-N
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Compound 3c
Molecular Weight:336.3084
Molecular Formula:C17H15F3N2O2
InChIKey:AZPGXQIFZRYYPR-UHFFFAOYSA-N
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Compound 3d
Molecular Weight:340.727
Molecular Formula:C16H12ClF3N2O
InChIKey:JIESHVBMEUHYEA-UHFFFAOYSA-N
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Compound 3e
Molecular Weight:385.178
Molecular Formula:C16H12BrF3N2O
InChIKey:SXGVFCOFQGJPFP-UHFFFAOYSA-N
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Compound 3f
Molecular Weight:324.2729
Molecular Formula:C16H12F4N2O
InChIKey:JQGTYNLNSVHKNQ-UHFFFAOYSA-N
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Compound 3g
Molecular Weight:312.31
Molecular Formula:C14H11F3N2OS
InChIKey:JZWGQBAKKRLTHN-UHFFFAOYSA-N
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Compound 3h
Molecular Weight:244.213
Molecular Formula:C11H11F3N2O
InChIKey:VBHCIOGDFULZCC-UHFFFAOYSA-N
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Compound 3i
Molecular Weight:334.3356
Molecular Formula:C18H17F3N2O
InChIKey:GQFKREZJKRDIIB-UHFFFAOYSA-N
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Compound 3j
Molecular Weight:288.292
Molecular Formula:C16H14F2N2O
InChIKey:MBJGKKKZHXJTPL-UHFFFAOYSA-N
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Compound 3k
Molecular Weight:302.3185
Molecular Formula:C17H16F2N2O
InChIKey:JVTBXIAMQYCDPT-UHFFFAOYSA-N
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Compound 3l
Molecular Weight:302.3185
Molecular Formula:C17H16F2N2O
InChIKey:VICGOQROPFWYGH-UHFFFAOYSA-N
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Compound 3m
Molecular Weight:322.737
Molecular Formula:C16H13ClF2N2O
InChIKey:NRXXGVIWYZECMJ-UHFFFAOYSA-N
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Compound 3n
Molecular Weight:318.3179
Molecular Formula:C17H16F2N2O2
InChIKey:SFRAFKZMOGYVJO-UHFFFAOYSA-N
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Compound 3o
Molecular Weight:252.311
Molecular Formula:C16H16N2O
InChIKey:WFKXBVVHUWWFIU-UHFFFAOYSA-N
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Compound 3p
Molecular Weight:314.3804
Molecular Formula:C21H18N2O
InChIKey:INIRFQYQJHZPEL-UHFFFAOYSA-N
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Compound 3q
Molecular Weight:336.3084
Molecular Formula:C17H15F3N2O2
InChIKey:LPYGYIRTKKIIFR-UHFFFAOYSA-N
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Compound 3s
Molecular Weight:314.3459
Molecular Formula:C16H21F3N2O
InChIKey:UOVMBKZWAYMRRP-UHFFFAOYSA-N
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Compound 3t
Molecular Weight:334.3356
Molecular Formula:C18H17F3N2O
InChIKey:JULMEIUJVCHVGK-UHFFFAOYSA-N
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Compound 3u
Molecular Weight:338.2995
Molecular Formula:C17H14F4N2O
InChIKey:NGTRWZSSWJJPBQ-UHFFFAOYSA-N
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Compound 3v
Molecular Weight:354.754
Molecular Formula:C17H14ClF3N2O
InChIKey:LFEDCLBDDJKYPL-UHFFFAOYSA-N
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Compound 3w
Molecular Weight:334.3356
Molecular Formula:C18H17F3N2O
InChIKey:WUYYFZOPDSYLFW-UHFFFAOYSA-N
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Compound 3y
Molecular Weight:294.3396
Molecular Formula:C16H20F2N2O
InChIKey:YLDHNJXMJMKMMM-UHFFFAOYSA-N
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Compound 3z
Molecular Weight:338.3506
Molecular Formula:C20H16F2N2O
InChIKey:OVPZICAMBOBSRX-UHFFFAOYSA-N
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Compound 5
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 5a
Molecular Weight:161.1574
Molecular Formula:C9H7NO2
InChIKey:VCYBVWFTGAZHGH-UHFFFAOYSA-N
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Compound 6
Molecular Weight:56.0633
Molecular Formula:C3H4O
InChIKey:HGINCPLSRVDWNT-UHFFFAOYSA-N
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Compound 7
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 7a
Molecular Weight:217.2206
Molecular Formula:C12H11NO3
InChIKey:YVFXAGOJBXIVQM-UHFFFAOYSA-N
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Compound 7b
Molecular Weight:251.666
Molecular Formula:C12H10ClNO3
InChIKey:MIYHZKDISYJLFW-UHFFFAOYSA-N
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Compound 7c
Molecular Weight:231.2472
Molecular Formula:C13H13NO3
InChIKey:FYHWQDBNUSTCMZ-UHFFFAOYSA-N
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Compound 7d
Molecular Weight:235.2111
Molecular Formula:C12H10FNO3
InChIKey:UDVXGESFPPYYFJ-UHFFFAOYSA-N
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Compound 7e
Molecular Weight:360.986
Molecular Formula:C11H7Br2NO3
InChIKey:KIQLFHNBEIXJIP-UHFFFAOYSA-N
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Compound 7f
Molecular Weight:296.117
Molecular Formula:C12H10BrNO3
InChIKey:ODTFMEYMLRZQAV-UHFFFAOYSA-N
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Compound 7g
Molecular Weight:296.117
Molecular Formula:C12H10BrNO3
InChIKey:BXWHENOWXLFTPP-UHFFFAOYSA-N
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Compound 7h
Molecular Weight:327.762
Molecular Formula:C18H14ClNO3
InChIKey:JERNHEIBMQVWFO-UHFFFAOYSA-N
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Compound 8
Molecular Weight:228.3106
Molecular Formula:C11H14F2OSi
InChIKey:DCDOQXGTFOHOCH-UHFFFAOYSA-N
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Compound 9
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 5i
Molecular Weight:181.576
Molecular Formula:C8H4ClNO2
InChIKey:XHDJYQWGFIBCEP-UHFFFAOYSA-N
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Compound 5j
Molecular Weight:161.1574
Molecular Formula:C9H7NO2
InChIKey:VAJCSPZKMVQIAP-UHFFFAOYSA-N
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Compound 9a
Molecular Weight:317.2868
Molecular Formula:C17H13F2NO3
InChIKey:VSCPIDHBHYFTOI-UHFFFAOYSA-N
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Compound 9b
Molecular Weight:337.705
Molecular Formula:C16H10ClF2NO3
InChIKey:UOQMVOBDESDQBX-UHFFFAOYSA-N
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Compound 9c
Molecular Weight:317.2868
Molecular Formula:C17H13F2NO3
InChIKey:IUXJRNYMKQOWAL-UHFFFAOYSA-N
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Compound 10
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 10a
Molecular Weight:106.1219
Molecular Formula:C7H6O
InChIKey:HUMNYLRZRPPJDN-UHFFFAOYSA-N
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Compound 10b
Molecular Weight:72.1057
Molecular Formula:C4H8O
InChIKey:AMIMRNSIRUDHCM-UHFFFAOYSA-N
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Compound 12
Molecular Weight:253.2943
Molecular Formula:C13H19NO4
InChIKey:LJXTYJXBORAIHX-UHFFFAOYSA-N
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Compound 13
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 13a
Molecular Weight:213.275
Molecular Formula:C14H15NO
InChIKey:Not Available
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Compound 13b
Molecular Weight:179.2588
Molecular Formula:C11H17NO
InChIKey:FYGQPDOYMGONFR-UHFFFAOYSA-N
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