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Keywords:

  • C[BOND]C bond formation;
  • C[BOND]H activation;
  • copper;
  • cycloaddition;
  • nitrones

Abstract

A copper-catalyzed migratory oxidative-coupling reaction between nitrones and various ethers/amines exhibited high functional-group tolerance. Even in aqueous media, the reaction proceeded efficiently. For practical use of this catalysis, a unique sequential Huisgen cycloaddition was demonstrated. Mechanistic investigations revealed that the reaction proceeded through oxidative catalytic activation of ethers/amines to afford iminium/oxonium intermediates by concurrent dual one-electron abstractions by copper(II) and oxyl radicals.

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Featured Compounds

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  1. 1 - 38
Compound 1
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 1a
Molecular Weight:193.1992
Molecular Formula:C10H11NO3
InChIKey:QCRWWMKODGJVDG-FLIBITNWSA-N
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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:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 2a
Molecular Weight:232.3166
Molecular Formula:C12H24O4
InChIKey:NMWPSPWREHKJRC-UHFFFAOYSA-N
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Compound 2b
Molecular Weight:198.3019
Molecular Formula:C12H22O2
InChIKey:OPQGBPADLAMZNZ-UHFFFAOYSA-N
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Compound 2c
Molecular Weight:170.2487
Molecular Formula:C10H18O2
InChIKey:IYMKLYPAYFEUGT-UHFFFAOYSA-N
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Compound 2d
Molecular Weight:196.286
Molecular Formula:C12H20O2
InChIKey:UXGIURGCTWITMW-UHFFFAOYSA-N
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Compound 2e
Molecular Weight:214.3013
Molecular Formula:C12H22O3
InChIKey:CUXSWIMIQHJJFC-UHFFFAOYSA-N
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Compound 2f
Molecular Weight:216.3172
Molecular Formula:C12H24O3
InChIKey:DTJOZGLLEHAUME-UHFFFAOYSA-N
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Compound 2g
Molecular Weight:234.334
Molecular Formula:C15H22O2
InChIKey:VDEPYOWPLQICCN-UHFFFAOYSA-N
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Compound 2h
Molecular Weight:518.5513
Molecular Formula:C24H38O12
InChIKey:AYNYAWYZBMMIJI-WHCFWRGISA-N
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Compound 2i
Molecular Weight:474.5897
Molecular Formula:C26H38N2O6
InChIKey:HUPASPVKFVFEAD-FQEVSTJZSA-N
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Compound 2j
Molecular Weight:451.5531
Molecular Formula:C24H37NO7
InChIKey:KXUKKVFZZJSZTK-SFHVURJKSA-N
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Compound 3aa
Molecular Weight:423.4999
Molecular Formula:C22H33NO7
InChIKey:JNTANHRKBPLPTR-HZHRSRAPSA-N
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Compound 3ab
Molecular Weight:389.4852
Molecular Formula:C22H31NO5
InChIKey:PYTUOWOWFKHLDF-KQWNVCNZSA-N
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Compound 3ab'
Molecular Weight:389.4852
Molecular Formula:C22H31NO5
InChIKey:HSIZZEQHLQWAFA-HZHRSRAPSA-N
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Compound 3ac
Molecular Weight:361.4321
Molecular Formula:C20H27NO5
InChIKey:HZKWZOWGONLCKH-FYJGNVAPSA-N
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Compound 3ad
Molecular Weight:387.4694
Molecular Formula:C22H29NO5
InChIKey:ISGATTIEMQZHND-KQWNVCNZSA-N
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Compound 3ae
Molecular Weight:405.4846
Molecular Formula:C22H31NO6
InChIKey:YXMWFOARLYPUEP-OEAKJJBVSA-N
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Compound 3af
Molecular Weight:407.5005
Molecular Formula:C22H33NO6
InChIKey:AMDMBMONLFWDGM-XQNSMLJCSA-N
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Compound 3ag
Molecular Weight:425.5173
Molecular Formula:C25H31NO5
InChIKey:SXRCQFULEZBGNS-NLRVBDNBSA-N
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Compound 3ah
Molecular Weight:709.7347
Molecular Formula:C34H47NO15
InChIKey:CPMHFYCJMVNBLD-ZOWQPXKNSA-N
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Compound 3ai
Molecular Weight:665.7731
Molecular Formula:C36H47N3O9
InChIKey:WXFPPBKWBOHALQ-XNJAMTHASA-N
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Compound 3aj
Molecular Weight:642.7364
Molecular Formula:C34H46N2O10
InChIKey:QOWTYEYIXSYBBT-UKIJMLNFSA-N
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Compound 2k
Molecular Weight:144.2114
Molecular Formula:C8H16O2
InChIKey:QVHATYNRLSVGKG-UHFFFAOYSA-N
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Compound 2l
Molecular Weight:72.1057
Molecular Formula:C4H8O
InChIKey:WYURNTSHIVDZCO-UHFFFAOYSA-N
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Compound 2m
Molecular Weight:121.1796
Molecular Formula:C8H11N
InChIKey:Not Available
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Compound 3ak
Molecular Weight:335.3948
Molecular Formula:C18H25NO5
InChIKey:RYQFZOTZXFSFSX-XDHOZWIPSA-N
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Compound 3al
Molecular Weight:263.2891
Molecular Formula:C14H17NO4
InChIKey:GASUZXGFAAHKFD-XNTDXEJSSA-N
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Compound 3am
Molecular Weight:312.363
Molecular Formula:C18H20N2O3
InChIKey:ZWPYEMDBYBQHAZ-DEDYPNTBSA-N
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Compound 1b
Molecular Weight:259.3004
Molecular Formula:C15H17NO3
InChIKey:HYFFZOYXHKIQFA-SSZFMOIBSA-N
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Compound 4
Molecular Weight:511.6147
Molecular Formula:C30H33N5O3
InChIKey:ZAXWMDMPOIAYIH-FADJLKOXSA-N
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Compound 2n
Molecular Weight:188.264
Molecular Formula:C10H20O3
InChIKey:AZLLKFGZCNUVBD-UHFFFAOYSA-N
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Compound 9
Molecular Weight:186.2481
Molecular Formula:C10H18O3
InChIKey:KGMVFMYSANCNAH-UHFFFAOYSA-N
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Compound 2o
Molecular Weight:177.2429
Molecular Formula:C11H15NO
InChIKey:VVGHYJTYYXOIGG-UHFFFAOYSA-N
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Compound 10
Molecular Weight:352.4699
Molecular Formula:C22H28N2O2
InChIKey:MJZIOEMNNMMPOC-UHFFFAOYSA-N
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Compound 11
Molecular Weight:265.305
Molecular Formula:C14H19NO4
InChIKey:XUJHZUPPALVPAM-XNTDXEJSSA-N
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