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Literature DB >> 32643945

Strain-Promoted Oxidation of Methylenecyclopropane Derivatives using N-Hydroxyphthalimide and Molecular Oxygen in the Dark.

Abstract

The hydroperoxidation of alkylidenecyclopropanes and other strained alkenes using an N-hydroxylamine and molecular oxygen occurred in the absence of catalyst, initiator, or light. The oxidation reaction proceeds through a radical pathway that is initiated by autoxidation of the alkene substrate. The hydroperoxides were converted to their corresponding alcohols and ketones under mild conditions.

Entities: Chemical Species

Year: 2020 PMID： 32643945 PMCID： PMC7368818 DOI： 10.1021/acs.orglett.0c02075

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

28 in total

1. Alkane Oxidation with Molecular Oxygen Using a New Efficient Catalytic System: N-Hydroxyphthalimide (NHPI) Combined with Co(acac)(n)() (n = 2 or 3).

Authors: Yasutaka Ishii; Takahiro Iwahama; Satoshi Sakaguchi; Kouichi Nakayama; Yutaka Nishiyama
Journal: J Org Chem Date: 1996-07-12 Impact factor: 4.354

2. An oxygen-deficient perovskite as selective catalyst in the oxidation of alkyl benzenes.

Authors: A Aguadero; H Falcon; J M Campos-Martin; S M Al-Zahrani; J L G Fierro; J A Alonso
Journal: Angew Chem Int Ed Engl Date: 2011-05-31 Impact factor: 15.336

3. Strain-promoted oxidative annulation of arynes and cyclooctynes with benzamides: palladium-catalyzed C-H/N-H activation for the synthesis of N-heterocycles.

Authors: Xianglong Peng; Weiguo Wang; Chao Jiang; Di Sun; Zhenghu Xu; Chen-Ho Tung
Journal: Org Lett Date: 2014-10-02 Impact factor: 6.005

Review 4. Catalytic Aerobic Oxidation of C(sp³ )-H Bonds.

Authors: Hans Sterckx; Bénédicte Morel; Bert U W Maes
Journal: Angew Chem Int Ed Engl Date: 2019-04-08 Impact factor: 15.336

5. Copper(I)-Catalyzed Oxidation of Alkenes Using Molecular Oxygen and Hydroxylamines: Synthesis and Reactivity of α-Oxygenated Ketones.

Authors: Alexander A Andia; Matthew R Miner; K A Woerpel
Journal: Org Lett Date: 2015-05-08 Impact factor: 6.005

6. N-Hydroxyphthalimide: a new photoredox catalyst for [4+1] radical cyclization of N-methylanilines with isocyanides.

Authors: Arvind K Yadav; Lal Dhar S Yadav
Journal: Chem Commun (Camb) Date: 2016-08-23 Impact factor: 6.222

7. Molecule-induced peroxide homolysis.

Authors: Natascia Turrà; Ulrich Neuenschwander; Ive Hermans
Journal: Chemphyschem Date: 2013-04-04 Impact factor: 3.102

8. Metal-free, NHPI catalyzed oxidative cleavage of C-C double bond using molecular oxygen as oxidant.

Authors: Riyuan Lin; Feng Chen; Ning Jiao
Journal: Org Lett Date: 2012-08-02 Impact factor: 6.005

9. A new route to lactam precursors from cycloalkanes: direct production of nitrosocycloalkanes or cycloalkanone oximes by using tert-butyl nitrite and N-hydroxyphthalimide.

Authors: Tomotaka Hirabayashi; Satoshi Sakaguchi; Yasutaka Ishii
Journal: Angew Chem Int Ed Engl Date: 2004-02-20 Impact factor: 15.336

Strain-Promoted Oxidation of Methylenecyclopropane Derivatives using N-Hydroxyphthalimide and Molecular Oxygen in the Dark.

1. Alkane Oxidation with Molecular Oxygen Using a New Efficient Catalytic System: N-Hydroxyphthalimide (NHPI) Combined with Co(acac)(n)() (n = 2 or 3).

2. An oxygen-deficient perovskite as selective catalyst in the oxidation of alkyl benzenes.

3. Strain-promoted oxidative annulation of arynes and cyclooctynes with benzamides: palladium-catalyzed C-H/N-H activation for the synthesis of N-heterocycles.

Review 4. Catalytic Aerobic Oxidation of C(sp³ )-H Bonds.

5. Copper(I)-Catalyzed Oxidation of Alkenes Using Molecular Oxygen and Hydroxylamines: Synthesis and Reactivity of α-Oxygenated Ketones.

6. N-Hydroxyphthalimide: a new photoredox catalyst for [4+1] radical cyclization of N-methylanilines with isocyanides.

7. Molecule-induced peroxide homolysis.

8. Metal-free, NHPI catalyzed oxidative cleavage of C-C double bond using molecular oxygen as oxidant.

9. A new route to lactam precursors from cycloalkanes: direct production of nitrosocycloalkanes or cycloalkanone oximes by using tert-butyl nitrite and N-hydroxyphthalimide.

10. Epidithiodiketopiperazines: Strain-Promoted Thiol-Mediated Cellular Uptake at the Highest Tension.

1. Chemiluminescence-promoted oxidation of alkyl enol ethers by NHPI under mild conditions and in the dark.

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

Review 4. Catalytic Aerobic Oxidation of C(sp3 )-H Bonds.

Review 4. Catalytic Aerobic Oxidation of C(sp³ )-H Bonds.