- O-Perfluoropyridin-4-yl Oximes: Iminyl Radical Precursors for Photo-or Thermal-Induced N-O Cleavage in C(sp2)-C(sp3) Bond Formation
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O-Perfluoropyridin-4-yl group was first installed onto cycloketone oximes as a new electrophore, which was proven to be efficient iminyl radical precursors under photocatalytic and thermal conditions. A range of O-perfluoropyridin-4-yl oximes were successfully utilized in C(sp2)-C(sp3) bond formations of quinoxalin-2(1H)-ones and alkenes, providing facile accesses to a range of functionalized alkylnitriles.
- Hu, Yuan-Zhuo,Li, Xu-Jie,Xia, Peng-Ju,Xiang, Hao-Yue,Yang, Hua,Ye, Zhi-Peng
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p. 3538 - 3547
(2020/03/23)
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- Photoinduced, Copper-Catalyzed Three-Component Annulation of gem-Dialkylthio Enynes
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Photoinduced, copper-catalyzed three-component radical annulation of gem-dialkylthio enynes, cyclobutanone oxime esters, and boronic acids was achieved, forming highly functionalized aryl thienyl sulfides with both good chemo- and diastereoselectivities. The reaction proceeds through a domino sequence involving cyanoalkyl radical-mediated intramolecular annulation of gem-dialkylthio enyne, alkenyl radical-promoted C(sp3)-S bond cleavage, and sulfur-centered radical-trapped Cu(II)-facilitated C-S cross-coupling. The protocol features simultaneous establishment of cyanoalkyl, cyclopentanone, and thiophene moieties and a thioether C-S bond in one pot with broad substrate scopes and versatile functional group tolerance under mild conditions.
- Lou, Jiang,Ma, Juan,Xu, Bao-Hua,Zhou, Yong-Gui,Yu, Zhengkun
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supporting information
p. 5202 - 5206
(2020/07/15)
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- Iminyl Radical-Triggered Intermolecular Distal C(sp3)-H Heteroarylation via 1,5-Hydrogen-Atom Transfer (HAT) Cascade
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An efficient iron-catalyzed intermolecular remote C(sp3)-H heteroarylation of alkyl ketones has been developed via an iminyl radical-triggered 1,5-hydrogen-atom transfer (HAT) cascade. This protocol was amenable to a wide variety of alkyl ketones and heteroaryls, thus providing a straightforward method for the late-stage functionalization of alkylketones and heteroaryls.
- Gu, Yu-Rui,Duan, Xin-Hua,Chen, Li,Ma, Zhi-Yong,Gao, Pin,Guo, Li-Na
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p. 917 - 920
(2019/02/14)
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- Carbonylation of tertiary carbon radicals: synthesis of lactams
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Herein, we disclose an interesting iron-catalyzed approach for the carbonylation of a tertiary carbon radical. The tertiary carbon radical generated from a 1,5-hydrogen atom transfer can be captured by CO gas smoothly. Various six-membered lactams were constructed chemo-selectively in high yields.
- Yin, Zhiping,Zhang, Zhuan,Zhang, Youcan,Dixneuf, Pierre H.,Wu, Xiao-Feng
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p. 4655 - 4658
(2019/05/09)
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- Amidyl Radical Directed Remote Allylation of Unactivated sp3 C?H Bonds by Organic Photoredox Catalysis
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The development of visible-light-mediated allylation of unactivated sp3 C?H bonds is reported. The remote allylation was directed by the amidyl radical, which was generated by photocatalytic fragmentation of a pre-functionalized amide precursor. Both aromatic and aliphatic amide derivatives could successfully deliver the remote C?H allylation products in good yields. A variety of electron deficient allyl sulfone systems could be used as δ-carbon radical acceptor.
- Wu, Kui,Wang, Lushun,Colón-Rodríguez, Sonivette,Flechsig, Gerd-Uwe,Wang, Ting
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supporting information
p. 1774 - 1778
(2019/01/16)
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- Iminyl Radical-Mediated Controlled Hydroxyalkylation of Remote C(sp3)-H Bond via Tandem 1,5-HAT and Difunctionalization of Aryl Alkenes
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A visible-light mediated γ-hydroxyalkylation of ketones via C(sp3)-H functionalization has been developed under redox neutral conditions. This protocol relies on the iminyl radical-triggered 1,5-HAT followed by oxyalkylation of alkenes, wherein C?C and C?O bonds were constructed in one step. This three-component reaction features mild conditions, wide substrate scope and excellent functional group tolerance, thus providing a facile and highly efficient access to complex valuable ketones. (Figure presented.).
- Ma, Zhi-Yong,Guo, Li-Na,Gu, Yu-Rui,Chen, Li,Duan, Xin-Hua
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p. 4341 - 4347
(2018/10/20)
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