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Literature DB >> 18213987

Synthesis using aromatic homolytic substitution--recent advances.

Abstract

This critical review aims at presenting recent developments in intramolecular aromatic homolytic substitution which has become one of the common methodologies in modern synthesis. The application of Bu3SnH-mediated cyclisations have proved especially useful. The critical review illustrates the mechanistic considerations required for planning synthetic applications and a wide range of synthetic protocols and natural product syntheses are shown. The latest evidence for the mechanisms involved in aromatic homolytic substitution are presented. (152 references).

Entities: Chemical

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Year: 2007 PMID： 18213987 DOI： 10.1039/b605183a

Source DB: PubMed Journal: Chem Soc Rev ISSN： 0306-0012 Impact factor: 54.564

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Cited

15 in total

1. Radical additions to aromatic residues in peptides facilitate unexpected side chain and backbone losses.

Authors: Xing Zhang; Ryan R Julian
Journal: J Am Soc Mass Spectrom Date: 2014-02-01 Impact factor: 3.109

2. Palladium-catalyzed, ring-forming aromatic C-H alkylations with unactivated alkyl halides.

Authors: Alexander R O Venning; Patrick T Bohan; Erik J Alexanian
Journal: J Am Chem Soc Date: 2015-03-16 Impact factor: 15.419

3. Practical radical cyclizations with arylboronic acids and trifluoroborates.

Authors: Jonathan W Lockner; Darryl D Dixon; Rune Risgaard; Phil S Baran
Journal: Org Lett Date: 2011-09-16 Impact factor: 6.005

4. Nickel-catalyzed, ring-forming aromatic C-H alkylations with unactivated alkyl halides.

Authors: Quentin D Tercenio; Erik J Alexanian
Journal: Tetrahedron Date: 2019-05-25 Impact factor: 2.457

5. Radical-based regioselective C-H functionalization of electron-deficient heteroarenes: scope, tunability, and predictability.

Authors: Fionn O'Hara; Donna G Blackmond; Phil S Baran
Journal: J Am Chem Soc Date: 2013-07-30 Impact factor: 15.419

6. Transition-Metal (Pd, Ni, Mn)-Catalyzed C-C Bond Constructions Involving Unactivated Alkyl Halides and Fundamental Synthetic Building Blocks.

Authors: Megan R Kwiatkowski; Erik J Alexanian
Journal: Acc Chem Res Date: 2019-03-25 Impact factor: 22.384

Synthesis using aromatic homolytic substitution--recent advances.

1. Radical additions to aromatic residues in peptides facilitate unexpected side chain and backbone losses.

2. Palladium-catalyzed, ring-forming aromatic C-H alkylations with unactivated alkyl halides.

3. Practical radical cyclizations with arylboronic acids and trifluoroborates.

4. Nickel-catalyzed, ring-forming aromatic C-H alkylations with unactivated alkyl halides.

5. Radical-based regioselective C-H functionalization of electron-deficient heteroarenes: scope, tunability, and predictability.

6. Transition-Metal (Pd, Ni, Mn)-Catalyzed C-C Bond Constructions Involving Unactivated Alkyl Halides and Fundamental Synthetic Building Blocks.

7. Direct alkylation of heteroaryls using potassium alkyl- and alkoxymethyltrifluoroborates.

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

9. Amine α-heteroarylation via photoredox catalysis: a homolytic aromatic substitution pathway.

10. Electrochemical oxidative decarboxylation and 1,2-aryl migration towards the synthesis of 1,2-diaryl ethers.