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Literature DB >> 24000186

Selective intermolecular amination of C-H bonds at tertiary carbon centers.

Jennifer L Roizen¹, David N Zalatan, J Du Bois.

Abstract

C-H insertion: A method for intermolecular amination of tertiary CH bonds is described that uses limiting amounts of substrate and a convenient phenol-derived nitrogen source. Structure-selectivity and mechanistic studies suggest that steric interaction between the substrate and active oxidant is the principal determinant of product selectivity.

Entities: CellLine Chemical Disease Gene

Keywords: C-H insertion; amination; amines; isotope effect; rhodium

Mesh：

Substances：

Year: 2013 PMID： 24000186 PMCID： PMC5483380 DOI： 10.1002/anie.201304238

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

30 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

3. Catalytic intermolecular amination of C-H bonds: method development and mechanistic insights.

Authors: Kristin Williams Fiori; J Du Bois
Journal: J Am Chem Soc Date: 2007-01-24 Impact factor: 15.419

4. Intermolecular C-H amination of complex molecules: insights into the factors governing the selectivity.

Authors: Camille Lescot; Benjamin Darses; Florence Collet; Pascal Retailleau; Philippe Dauban
Journal: J Org Chem Date: 2012-08-28 Impact factor: 4.354

5. A diruthenium catalyst for selective, intramolecular allylic C-H amination: reaction development and mechanistic insight gained through experiment and theory.

Authors: Mark Edwin Harvey; Djamaladdin G Musaev; J Du Bois
Journal: J Am Chem Soc Date: 2011-10-07 Impact factor: 15.419

6. A unique and highly efficient method for catalytic olefin aziridination.

Authors: Kiran Guthikonda; J Du Bois
Journal: J Am Chem Soc Date: 2002-11-20 Impact factor: 15.419

7. Metal-catalyzed nitrogen-atom transfer methods for the oxidation of aliphatic C-H bonds.

Authors: Jennifer L Roizen; Mark Edwin Harvey; J Du Bois
Journal: Acc Chem Res Date: 2012-04-30 Impact factor: 22.384

8. Toward a synthetically useful stereoselective C-H amination of hydrocarbons.

Authors: Chungen Liang; Florence Collet; Fabien Robert-Peillard; Paul Müller; Robert H Dodd; Philippe Dauban
Journal: J Am Chem Soc Date: 2007-12-12 Impact factor: 15.419

9. Diastereotopos-differentiation in the Rh-catalyzed amination of benzylic methylene groups in the α-position to a stereogenic center.

Authors: Anike Nörder; Sarah A Warren; Eberhardt Herdtweck; Stefan M Huber; Thorsten Bach
Journal: J Am Chem Soc Date: 2012-08-06 Impact factor: 15.419

10. Complex N-heterocycle synthesis via iron-catalyzed, direct C-H bond amination.

Authors: Elisabeth T Hennessy; Theodore A Betley
Journal: Science Date: 2013-05-03 Impact factor: 47.728

25 in total

1. Mechanism and Dynamics of Intramolecular C-H Insertion Reactions of 1-Aza-2-azoniaallene Salts.

Authors: Xin Hong; Daniel A Bercovici; Zhongyue Yang; Nezar Al-Bataineh; Ramya Srinivasan; Ram C Dhakal; K N Houk; Matthias Brewer
Journal: J Am Chem Soc Date: 2015-07-07 Impact factor: 15.419

2. Convergent and Biomimetic Enantioselective Total Synthesis of (-)-Communesin F.

Authors: Stephen P Lathrop; Matthew Pompeo; Wen-Tau T Chang; Mohammad Movassaghi
Journal: J Am Chem Soc Date: 2016-06-14 Impact factor: 15.419

3. Alkylation of Sulfonamides with Trichloroacetimidates under Thermal Conditions.

Authors: Daniel R Wallach; John D Chisholm
Journal: J Org Chem Date: 2016-08-10 Impact factor: 4.354

4. Concise Synthesis of (-)-Hodgkinsine, (-)-Calycosidine, (-)-Hodgkinsine B, (-)-Quadrigemine C, and (-)-Psycholeine via Convergent and Directed Modular Assembly of Cyclotryptamines.

Authors: Petra Lindovska; Mohammad Movassaghi
Journal: J Am Chem Soc Date: 2017-11-20 Impact factor: 15.419

Selective intermolecular amination of C-H bonds at tertiary carbon centers.

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

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

3. Catalytic intermolecular amination of C-H bonds: method development and mechanistic insights.

4. Intermolecular C-H amination of complex molecules: insights into the factors governing the selectivity.

5. A diruthenium catalyst for selective, intramolecular allylic C-H amination: reaction development and mechanistic insight gained through experiment and theory.

6. A unique and highly efficient method for catalytic olefin aziridination.

7. Metal-catalyzed nitrogen-atom transfer methods for the oxidation of aliphatic C-H bonds.

8. Toward a synthetically useful stereoselective C-H amination of hydrocarbons.

9. Diastereotopos-differentiation in the Rh-catalyzed amination of benzylic methylene groups in the α-position to a stereogenic center.

10. Complex N-heterocycle synthesis via iron-catalyzed, direct C-H bond amination.

1. Mechanism and Dynamics of Intramolecular C-H Insertion Reactions of 1-Aza-2-azoniaallene Salts.

2. Convergent and Biomimetic Enantioselective Total Synthesis of (-)-Communesin F.

3. Alkylation of Sulfonamides with Trichloroacetimidates under Thermal Conditions.

4. Concise Synthesis of (-)-Hodgkinsine, (-)-Calycosidine, (-)-Hodgkinsine B, (-)-Quadrigemine C, and (-)-Psycholeine via Convergent and Directed Modular Assembly of Cyclotryptamines.

5. Sulfamate Esters Guide Selective Radical-Mediated Chlorination of Aliphatic C-H Bonds.

Review 6. Applications of Nonenzymatic Catalysts to the Alteration of Natural Products.

7. Discovery of C13-Aminobenzoyl Cycloheximide Derivatives that Potently Inhibit Translation Elongation.

8. Total Synthesis and Stereochemical Assignment of (-)-Psychotridine.

Review 9. Transition-Metal-Catalyzed Selective Functionalization of C(sp³ )-H Bonds in Natural Products.

10. Enantioselective Intermolecular C-H Amination Directed by a Chiral Cation.

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

Review 6. Applications of Nonenzymatic Catalysts to the Alteration of Natural Products.

Review 9. Transition-Metal-Catalyzed Selective Functionalization of C(sp3 )-H Bonds in Natural Products.

Review 9. Transition-Metal-Catalyzed Selective Functionalization of C(sp³ )-H Bonds in Natural Products.