Copper-Catalyzed Aerobic Oxidative Intramolecular Alkene C–H Amination Leading to <i>N</i>-Heterocycles

Lu, Juyou; Jin, Ya; Liu, Hongxia; Jiang, Yuyang; Fu, Hua

doi:10.1021/ol2013395

Cited by 78 publications

(31 citation statements)

References 84 publications

(25 reference statements)

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“…102 Specifically, pyridyl substituted 3-methyleneisoindolin-1-ones were treated with catalytic copper(II) trifluoroacetate under air to afford the polycyclic N -heterocycles in good yield (Scheme 50). Limitations to the method include little allowance for structural changes in the substrate and the requirement of several equivalents of pivalic acid.…”

Section: Reactions Of Hydrocarbonsmentioning

confidence: 99%

Aerobic Copper-Catalyzed Organic Reactions

et al. 2013

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24 peroxide [Cu I (pyr)(tpb)] 10 mol % TBHP, 1 atm O 2 , 1:2 AcOH/pyr, rt, 24 h ∼2.5 26 74 g 35 25 n-hexane aldehyde CuCl 2 , 18-crown-6 1 atm O 2 , MeCHO, CH 2 Cl 2 , 70 °C, 24 h 2.4 91 h 9 34a 26 n-decane aldehyde Cu II Cl 16 Pc-AM(PS) 3 equiv of PhCHO, MeCN, 1 atm O 2 , 50 °C 15.4 100 i 61 a See Chart 2 for ligand structures. b Also 28% cyclohexene. c Also 26% cyclohexene. d Mixture of alcohol and hydroperoxide. e Remainder of product is cyclohexene. f Approximately 93:7 of 1-adamantol/2-adamantol. g Approximately 98:2 of 1-adamantol/2-adamantol. h Afforded oxidation products in an approximately 1:1 ratio at the 2-and 3-positions. i Mixture of decanones.

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Section: Reactions Of Hydrocarbonsmentioning

confidence: 99%

Aerobic Copper-Catalyzed Organic Reactions

et al. 2013

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“…Fu and co-workers have developed a similar strategy for the intramolecular oxidative amination of vinylic C À H bonds. [97] By treating substituted 3-benzylidene-2-pyridin-2ylmethyl-2,3-dihydro-isoindol-1-ones with 20 mol % Cu-(O 2 CCF 3 ) 2 donating groups led to slightly higher yields than those containing electron-withdrawing substituents, and the reaction was tolerant of C-Cl/Br bonds.…”

Section: Oxidative Annulation Reactionsmentioning

confidence: 99%

Copper‐Catalyzed Aerobic Oxidative CH Functionalizations: Trends and Mechanistic Insights

2011

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The selective oxidation of C-H bonds and the use of O(2) as a stoichiometric oxidant represent two prominent challenges in organic chemistry. Copper(II) is a versatile oxidant, capable of promoting a wide range of oxidative coupling reactions initiated by single-electron transfer (SET) from electron-rich organic molecules. Many of these reactions can be rendered catalytic in Cu by employing molecular oxygen as a stoichiometric oxidant to regenerate the active copper(II) catalyst. Meanwhile, numerous other recently reported Cu-catalyzed C-H oxidation reactions feature substrates that are electron-deficient or appear unlikely to undergo single-electron transfer to copper(II). In some of these cases, evidence has been obtained for the involvement of organocopper(III) intermediates in the reaction mechanism. Organometallic C-H oxidation reactions of this type represent important new opportunities for the field of Cu-catalyzed aerobic oxidations.

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“…The corresponding N-heterocycles 1,4-dihydropyrazine derivatives were obtained in good to excellent yields with wide functional group tolerance [183]. Bi, Zhang et al reported a novel Cu(OTf ) 2 -catalyzed preparation of benzoxazine derivatives from readily available N-para-tolylamides in the presence of Selectfluor and water through the intermolecular C-H-activated dehydrogenative cross-coupling reaction (Scheme 8.111).…”

Section: Copper-catalyzed Synthesis Of 14-dihydropyrazine Derivativesmentioning

confidence: 99%