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Literature DB >> 11322540

The persistent radical effect in organic synthesis.

Abstract

The persistent radical effect (PRE) is a principle that explains the highly selective cross-coupling between a persistent and a transient radical when both species are formed at equal rates. In this paper, the concept of the PRE is briefly discussed. Applications of the PRE in different reactions such as Co-mediated radical addition and cyclization reactions, Kharasch reactions catalyzed by transition metals, the Barton reaction, and our nitroxide-mediated tin-free radical cyclizations are presented. Some future perspectives for the PRE in organic synthesis are also provided.

Entities: Chemical

Year: 2001 PMID： 11322540 DOI： 10.1002/1521-3765(20010316)7:6<1159::aid-chem1159>3.0.co;2-i

Source DB: PubMed Journal: Chemistry ISSN： 0947-6539 Impact factor: 5.236

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Cited

45 in total

1. Forging C(sp³)-C(sp³) Bonds with Carbon-Centered Radicals in the Synthesis of Complex Molecules.

Authors: Spencer P Pitre; Nicholas A Weires; Larry E Overman
Journal: J Am Chem Soc Date: 2019-01-04 Impact factor: 15.419

Review 2. Synthesis of Tri- and Difluoromethoxylated Compounds by Visible-Light Photoredox Catalysis.

Authors: Johnny W Lee; Katarzyna N Lee; Ming-Yu Ngai
Journal: Angew Chem Int Ed Engl Date: 2019-05-28 Impact factor: 15.336

3. A Radical Approach to Anionic Chemistry: Synthesis of Ketones, Alcohols, and Amines.

Authors: Shengyang Ni; Natalia M Padial; Cian Kingston; Julien C Vantourout; Daniel C Schmitt; Jacob T Edwards; Monika M Kruszyk; Rohan R Merchant; Pavel K Mykhailiuk; Brittany B Sanchez; Shouliang Yang; Matthew A Perry; Gary M Gallego; James J Mousseau; Michael R Collins; Robert J Cherney; Pavlo S Lebed; Jason S Chen; Tian Qin; Phil S Baran
Journal: J Am Chem Soc Date: 2019-04-16 Impact factor: 15.419

Review 4. The electron is a catalyst.

Authors: Armido Studer; Dennis P Curran
Journal: Nat Chem Date: 2014-09 Impact factor: 24.427

5. Design of a Photoredox Catalyst that Enables the Direct Synthesis of Carbamate-Protected Primary Amines via Photoinduced, Copper-Catalyzed N-Alkylation Reactions of Unactivated Secondary Halides.

Authors: Jun Myun Ahn; Jonas C Peters; Gregory C Fu
Journal: J Am Chem Soc Date: 2017-12-04 Impact factor: 15.419

6. Oxodealkenylative Cleavage of Alkene C(sp³ )-C(sp² ) Bonds: A Practical Method for Introducing Carbonyls into Chiral Pool Materials.

Authors: Andrew J Smaligo; Jason Wu; Nikolas R Burton; Allison S Hacker; Aslam C Shaikh; Jason C Quintana; Ruoxi Wang; Changmin Xie; Ohyun Kwon
Journal: Angew Chem Int Ed Engl Date: 2019-12-02 Impact factor: 15.336

The persistent radical effect in organic synthesis.

1. Forging C(sp³)-C(sp³) Bonds with Carbon-Centered Radicals in the Synthesis of Complex Molecules.

Review 2. Synthesis of Tri- and Difluoromethoxylated Compounds by Visible-Light Photoredox Catalysis.

3. A Radical Approach to Anionic Chemistry: Synthesis of Ketones, Alcohols, and Amines.

Review 4. The electron is a catalyst.

5. Design of a Photoredox Catalyst that Enables the Direct Synthesis of Carbamate-Protected Primary Amines via Photoinduced, Copper-Catalyzed N-Alkylation Reactions of Unactivated Secondary Halides.

6. Oxodealkenylative Cleavage of Alkene C(sp³ )-C(sp² ) Bonds: A Practical Method for Introducing Carbonyls into Chiral Pool Materials.

7. Redox-Neutral TEMPO Catalysis: Direct Radical (Hetero)Aryl C-H Di- and Trifluoromethoxylation.

8. Roles of Iron Complexes in Catalytic Radical Alkene Cross-Coupling: A Computational and Mechanistic Study.

Review 9. Some aspects of radical cascade and relay reactions.

Review 10. Catalyzing Electrosynthesis: A Homogeneous Electrocatalytic Approach to Reaction Discovery.

The persistent radical effect in organic synthesis.

1. Forging C(sp3)-C(sp3) Bonds with Carbon-Centered Radicals in the Synthesis of Complex Molecules.

Review 2. Synthesis of Tri- and Difluoromethoxylated Compounds by Visible-Light Photoredox Catalysis.

3. A Radical Approach to Anionic Chemistry: Synthesis of Ketones, Alcohols, and Amines.

Review 4. The electron is a catalyst.

5. Design of a Photoredox Catalyst that Enables the Direct Synthesis of Carbamate-Protected Primary Amines via Photoinduced, Copper-Catalyzed N-Alkylation Reactions of Unactivated Secondary Halides.

6. Oxodealkenylative Cleavage of Alkene C(sp3 )-C(sp2 ) Bonds: A Practical Method for Introducing Carbonyls into Chiral Pool Materials.

7. Redox-Neutral TEMPO Catalysis: Direct Radical (Hetero)Aryl C-H Di- and Trifluoromethoxylation.

8. Roles of Iron Complexes in Catalytic Radical Alkene Cross-Coupling: A Computational and Mechanistic Study.

Review 9. Some aspects of radical cascade and relay reactions.

Review 10. Catalyzing Electrosynthesis: A Homogeneous Electrocatalytic Approach to Reaction Discovery.

1. Forging C(sp³)-C(sp³) Bonds with Carbon-Centered Radicals in the Synthesis of Complex Molecules.

6. Oxodealkenylative Cleavage of Alkene C(sp³ )-C(sp² ) Bonds: A Practical Method for Introducing Carbonyls into Chiral Pool Materials.