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Literature DB >> 22276612

Intermolecular Ritter-type C-H amination of unactivated sp3 carbons.

Quentin Michaudel¹, Damien Thevenet, Phil S Baran.

Abstract

Intermolecular Ritter-type C-H amination of unactivated sp(3) carbons has been developed. This new reaction proceeds under mild conditions using readily available reagents and an inexpensive source of nitrogen (acetonitrile). A broad scope of substrates can be aminated with this method since many functional groups are tolerated. This reaction also allows for the direct, innate C-H amination of a variety of hydrocarbons such as cyclohexane without the need of prefunctionalization or installation of a directing group.

Entities: Chemical Gene Species

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Year: 2012 PMID： 22276612 PMCID： PMC3277284 DOI： 10.1021/ja212020b

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

29 in total

1. Highly regioselective amination of unactivated alkanes by hypervalent sulfonylimino-λ³-bromane.

Authors: Masahito Ochiai; Kazunori Miyamoto; Takao Kaneaki; Satoko Hayashi; Waro Nakanishi
Journal: Science Date: 2011-04-22 Impact factor: 47.728

Review 2. Catalytic C-H amination: recent progress and future directions.

Authors: Florence Collet; Robert H Dodd; Philippe Dauban
Journal: Chem Commun (Camb) Date: 2009-07-07 Impact factor: 6.222

Review 3. Selectfluor: mechanistic insight and applications.

Authors: Paul T Nyffeler; Sergio Gonzalez Durón; Michael D Burkart; Stéphane P Vincent; Chi-Huey Wong
Journal: Angew Chem Int Ed Engl Date: 2004-12-27 Impact factor: 15.336

4. Efficient diastereoselective intermolecular rhodium-catalyzed C-H amination.

Authors: Chungen Liang; Fabien Robert-Peillard; Corinne Fruit; Paul Müller; Robert H Dodd; Philippe Dauban
Journal: Angew Chem Int Ed Engl Date: 2006-07-10 Impact factor: 15.336

Review 5. Bystanding F+ oxidants enable selective reductive elimination from high-valent metal centers in catalysis.

Authors: Keary M Engle; Tian-Sheng Mei; Xisheng Wang; Jin-Quan Yu
Journal: Angew Chem Int Ed Engl Date: 2011-01-24 Impact factor: 15.336

6. Investigations in the transition metal catalyzed aziridination of olefins, amination, and other insertion reactions with Bromamine-T as the source of nitrene.

Authors: B M Chanda; R Vyas; A V Bedekar
Journal: J Org Chem Date: 2001-01-12 Impact factor: 4.354

7. Expanding the scope of C-H amination through catalyst design.

Authors: Christine G Espino; Kristin Williams Fiori; Mihyong Kim; J Du Bois
Journal: J Am Chem Soc Date: 2004-12-01 Impact factor: 15.419

8. Total synthesis of eudesmane terpenes by site-selective C-H oxidations.

Authors: Ke Chen; Phil S Baran
Journal: Nature Date: 2009-05-13 Impact factor: 49.962

9. 1,3-Diol synthesis via controlled, radical-mediated C-H functionalization.

Authors: Ke Chen; Jeremy M Richter; Phil S Baran
Journal: J Am Chem Soc Date: 2008-05-16 Impact factor: 15.419

10. Amination of benzylic C-H bonds by arylazides catalyzed by CoII-porphyrin complexes: a synthetic and mechanistic study.

Authors: Fabio Ragaini; Andrea Penoni; Emma Gallo; Stefano Tollari; Claudia Li Gotti; Marta Lapadula; Enrica Mangioni; Sergio Cenini
Journal: Chemistry Date: 2003-01-03 Impact factor: 5.236

39 in total

1. Electrophotocatalytic diamination of vicinal C-H bonds.

Authors: Tao Shen; Tristan H Lambert
Journal: Science Date: 2021-02-04 Impact factor: 47.728

2. An efficient three-component synthesis of highly functionalized tetrahydroacenaphtho[1,2-b]indolone derivatives catalyzed by L-proline.

Authors: Juan-Juan Zhang; Xian Feng; Xue-Cheng Liu; Zhi-Bin Huang; Da-Qing Shi
Journal: Mol Divers Date: 2014-08-24 Impact factor: 2.943

Review 3. Copper-Promoted Functionalization of Organic Molecules: from Biologically Relevant Cu/O₂ Model Systems to Organometallic Transformations.

Authors: Rachel Trammell; Khashayar Rajabimoghadam; Isaac Garcia-Bosch
Journal: Chem Rev Date: 2019-01-30 Impact factor: 60.622

10. Simultaneous structure-activity studies and arming of natural products by C-H amination reveal cellular targets of eupalmerin acetate.

Authors: Jing Li; Justin S Cisar; Cong-Ying Zhou; Brunilda Vera; Howard Williams; Abimael D Rodríguez; Benjamin F Cravatt; Daniel Romo
Journal: Nat Chem Date: 2013-05-19 Impact factor: 24.427

Intermolecular Ritter-type C-H amination of unactivated sp3 carbons.

1. Highly regioselective amination of unactivated alkanes by hypervalent sulfonylimino-λ³-bromane.

Review 2. Catalytic C-H amination: recent progress and future directions.

Review 3. Selectfluor: mechanistic insight and applications.

4. Efficient diastereoselective intermolecular rhodium-catalyzed C-H amination.

Review 5. Bystanding F+ oxidants enable selective reductive elimination from high-valent metal centers in catalysis.

6. Investigations in the transition metal catalyzed aziridination of olefins, amination, and other insertion reactions with Bromamine-T as the source of nitrene.

7. Expanding the scope of C-H amination through catalyst design.

8. Total synthesis of eudesmane terpenes by site-selective C-H oxidations.

9. 1,3-Diol synthesis via controlled, radical-mediated C-H functionalization.

10. Amination of benzylic C-H bonds by arylazides catalyzed by CoII-porphyrin complexes: a synthetic and mechanistic study.

1. Electrophotocatalytic diamination of vicinal C-H bonds.

2. An efficient three-component synthesis of highly functionalized tetrahydroacenaphtho[1,2-b]indolone derivatives catalyzed by L-proline.

Review 3. Copper-Promoted Functionalization of Organic Molecules: from Biologically Relevant Cu/O₂ Model Systems to Organometallic Transformations.

4. A Highly Selective Vanadium Catalyst for Benzylic C-H Oxidation.

5. Direct C-C Bond Formation from Alkanes Using Ni-Photoredox Catalysis.

6. Directed amination of non-acidic arene C-H bonds by a copper-silver catalytic system.

7. Metal-Catalyzed and Metal-Free Intermolecular Amination of Light Alkanes and Benzenes.

8. Copper-catalyzed oxidative amination and allylic amination of alkenes.

9. Fe(III)/NaBH4-mediated free radical hydrofluorination of unactivated alkenes.

10. Simultaneous structure-activity studies and arming of natural products by C-H amination reveal cellular targets of eupalmerin acetate.

Review 2. Catalytic C-H amination: recent progress and future directions.

Review 3. Selectfluor: mechanistic insight and applications.

Review 5. Bystanding F+ oxidants enable selective reductive elimination from high-valent metal centers in catalysis.

Review 3. Copper-Promoted Functionalization of Organic Molecules: from Biologically Relevant Cu/O2 Model Systems to Organometallic Transformations.

Review 3. Copper-Promoted Functionalization of Organic Molecules: from Biologically Relevant Cu/O₂ Model Systems to Organometallic Transformations.