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Literature DB >> 26997205

Metal-free C(sp(3))-H functionalization: oxidative carbo-oxygenation of α-diazo carbonyls via radical dediazotization.

Nan-Nan Wang¹, Wen-Juan Hao, Tian-Shu Zhang, Guigen Li, Ya-Nan Wu, Shu-Jiang Tu, Bo Jiang.

Abstract

A novel three-component carbo-oxygenation of α-diazo carbonyls for flexible synthesis of unprecedented α-aminooxy-β-amino ketones has been established through metal-free C(sp(3))-H functionalization from readily accessible N,N-dimethylanilines and N-hydroxyphthalimide. The reaction pathway involves an in situ-generated phthalimide N-oxyl radical-triggered dediazotization/radical coupling sequence, leading to C-O and C-C bond formation.

Entities: Chemical Species

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Year: 2016 PMID： 26997205 PMCID： PMC4818971 DOI： 10.1039/c6cc00816j

Source DB: PubMed Journal: Chem Commun (Camb) ISSN： 1359-7345 Impact factor: 6.222

61 in total

1. Catalytic C-H Activation of sp(3) C-H Bonds in alpha-Position to a Nitrogen Atom-Two New Approaches I thank Professor E. Winterfeldt for his generous support of my research.

Authors: Sven Doye
Journal: Angew Chem Int Ed Engl Date: 2001-09-17 Impact factor: 15.336

2. Reactivity and mechanistic insight into visible-light-induced aerobic cross-dehydrogenative coupling reaction by organophotocatalysts.

Authors: Qiang Liu; Ya-Nan Li; Hui-Hui Zhang; Bin Chen; Chen-Ho Tung; Li-Zhu Wu
Journal: Chemistry Date: 2011-12-08 Impact factor: 5.236

Metal-free C(sp(3))-H functionalization: oxidative carbo-oxygenation of α-diazo carbonyls via radical dediazotization.

1. Catalytic C-H Activation of sp(3) C-H Bonds in alpha-Position to a Nitrogen Atom-Two New Approaches I thank Professor E. Winterfeldt for his generous support of my research.

2. Reactivity and mechanistic insight into visible-light-induced aerobic cross-dehydrogenative coupling reaction by organophotocatalysts.

3. From C(sp2)-H to C(sp3)-H: systematic studies on transition metal-catalyzed oxidative C-C formation.

4. Total synthesis of kinamycins C, F, and J.

5. The redox-neutral approach to C-H functionalization.

6. Functionalization of organic molecules by transition-metal-catalyzed C(sp3)-H activation.

Review 7. Nitroxide-mediated radical processes.

Review 8. Selective functionalisation of saturated C-H bonds with metalloporphyrin catalysts.

9. Late metal carbene complexes generated by multiple C-H activations: examining the continuum of M=C bond reactivity.

10. Catalytic arylsulfonyl radical-triggered 1,5-enyne-bicyclizations and hydrosulfonylation of α,β-conjugates.

1. Copper-Catalyzed Annulation-Cyanotrifluoromethylation of 1,6-Enynes Toward 1-Indanones via a Radical Process.

2. A Carbene-Extended ATRA Reaction.

3. Synthesis of N-alkoxyphthalimide derivatives via PIDA-promoted cross dehydrogenative coupling reaction.