Kaur, Jaspreet and Barham, Joshua P. (2022) Site-Selective C(sp(3))-H Functionalizations Mediated by Hydrogen Atom Transfer Reactions via alpha-Amino/alpha-Amido Radicals. SYNTHESIS-STUTTGART, 54 (06). pp. 1461-1477. ISSN 0039-7881, 1437-210X
Full text not available from this repository. (Request a copy)Abstract
Amines and amides, as N-containing compounds, are ubiquitous in pharmaceutically-active scaffolds, natural products, agrochemicals, and peptides. Amides in nature bear a key responsibility for imparting three-dimensional structure, such as in proteins. Structural modifications to amines and amides, especially at their positions. to N, bring about profound changes in biological activity oftentimes leading to more desirable pharmacological profiles of small drug molecules. A number of recent developments in synthetic methodology for the functionalizations of amines and amides omit the need of their directing groups or pre-functionalizations, achieving direct activation of the otherwise relatively benign C(sp(3))-H bonds. to N. Among these, hydrogen atom transfer (HAT) has proven a very powerful platform for the selective activation of amines and amides to their alpha-amino and alpha-amido radicals, which can then be employed to furnish C-C and C-X (X = heteroatom) bonds. The abilities to both form these radicals and control their reactivity in a site-selective manner is of utmost importance for such chemistries to witness applications in late-stage functionalization. Therefore, this review captures contemporary HAT strategies to realize chemo- and regioselective amine and amide alpha-C(sp(3))-H functionalization, based on bond strengths, bond polarities, reversible HAT equilibria, traceless electrostatic-directing auxiliaries, and steric effects of in situ-generated HAT agents.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | LATE-STAGE FUNCTIONALIZATION; H BOND FUNCTIONALIZATION; 1,4-ADDITION REACTIONS; PHOTOREDOX CATALYSIS; AMINOALKYL RADICALS; N-DEMETHYLATION; TERTIARY-AMINES; LIGHT; ARYLATION; AMIDOALKYLATION; C-H functionalization; hydrogen atom transfer; N-radical cation; alpha-amino radical; alpha-amido radical; photocatalysis; regioselectivity; late-stage functionalization |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie |
| Depositing User: | Petra Gürster |
| Date Deposited: | 12 Oct 2023 06:23 |
| Last Modified: | 29 Feb 2024 14:47 |
| URI: | https://pred.uni-regensburg.de/id/eprint/56680 |
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