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Literature DB >> 28097790

Visible-Light-Mediated Remote Aliphatic C-H Functionalizations through a 1,5-Hydrogen Transfer Cascade.

Abstract

A redox-neutral, light-mediated functionalization of unactivated C(sp3 )-H bonds via iminyl radicals is presented here. A 1,5-H transfer followed by the functionalization of a C(sp2 )-H bond takes place in aqueous media producing a variety of elaborated fused ketones. Mechanistic investigations have revealed 1,5-H transfer as the reversible, rate-determining step in this transformation. Divergent scaffolds are also accessible via C(sp3 )-N bond formation upon a careful choice of the reaction additives.

Entities: Chemical Species

Keywords: 1,5-H transfer; C−H functionalization; dihydro-2H-pyrrole; photoredox reactions; tetralone

Year: 2017 PMID： 28097790 DOI： 10.1002/anie.201609885

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

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Cited

28 in total

10. Palladium-Catalyzed Atom-Transfer Radical Cyclization at Remote Unactivated C(sp³ )-H Sites: Hydrogen-Atom Transfer of Hybrid Vinyl Palladium Radical Intermediates.

Authors: Maxim Ratushnyy; Marvin Parasram; Yang Wang; Vladimir Gevorgyan
Journal: Angew Chem Int Ed Engl Date: 2018-02-06 Impact factor: 15.336

Visible-Light-Mediated Remote Aliphatic C-H Functionalizations through a 1,5-Hydrogen Transfer Cascade.

1. General, Mild, and Selective Method for Desaturation of Aliphatic Amines.

2. Heck Reaction of Electronically Diverse Tertiary Alkyl Halides.

3. Sulfamate Esters Guide C(3)-Selective Xanthylation of Alkanes.

4. Catalytic Alkene Difunctionalization via Imidate Radicals.

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

6. Directed β C-H Amination of Alcohols via Radical Relay Chaperones.

7. Remote Allylation of Unactivated C(sp³)-H Bonds Triggered by Photogenerated Amidyl Radicals.

8. Remote C-H Functionalization via Selective Hydrogen Atom Transfer.

9. General, Auxiliary-Enabled Photoinduced Pd-Catalyzed Remote Desaturation of Aliphatic Alcohols.

10. Palladium-Catalyzed Atom-Transfer Radical Cyclization at Remote Unactivated C(sp³ )-H Sites: Hydrogen-Atom Transfer of Hybrid Vinyl Palladium Radical Intermediates.