Generation of aryl radicals from arylboronic acids by manganese(III) acetate: Synthesis of biaryls and heterobiaryls

Date

2003-01-24

Author

Demir, Ayhan Sıtkı
Reis, O
Emrullahoglu, M

Metadata

Show full item record

This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

Item Usage Stats

61
views

0
downloads

The efficient generation of aryl radicals from arylboronic acids by manganese(III) acetate is described. In aromatic solvents, in situ generated aryl radicals afford the corresponding biaryls in very good yields. This method works selectively, and yields are better than those from similar, previously described methods. Arylboronic acids carrying sensitive functional groups also work efficiently.

Subject Keywords

Thiophenes, Hydrocarbons, Lipids, Aromatic compounds, Organic compounds

URI

https://hdl.handle.net/11511/58029

Journal

JOURNAL OF ORGANIC CHEMISTRY

DOI

https://doi.org/10.1021/jo026466c

Collections

Department of Chemistry, Article

Suggestions

OpenMETU
Core

Novel conversion of thiols into disulfides, via S-nitrosothiol intermediates using trichloronitromethane Demir, Ayhan Sıtkı; Igdir, AC; Mahasneh, AS (1999-10-15) An efficient oxidative coupling of thiols to give disulfides via thionitrite (S-nitrosothiol) intermediate is described using trichloronitromethane as an efficient reagent in organic solvents and water. Cysteine and glutathione are converted into the corresponding disulfides in water in high yields.
Synthesis of 1,2,3,5- tetrasubstituted pyrrole derivatives via 5-exo-dig type cyclization and stereoselective functionalisation of ferrocene derivatives Kayalar, Metin; Demir, Ayhan Sıtkı; Department of Chemistry (2005) A convenient and new method for the synthesis of 1,2,3,5-tetrasubstituted pyrrole derivatives starting from 1,3,-dicarbonyl compounds through acid catalyzed cyclization reaction is described. Alkylation of 1,3-dicarbonyl compound with propargyl bromide followed by one step cyclization with the introduction of primary amines in the presence of catalytic amount of triflouroacetic acid (TFA) affords the corresponding pyrrole derivatives in high yields. The investigations on the studies of developing a new meth...
Reactions of 2-substituted epichlorohydrins Tanyeli, Cihangir; Akhmedov, IM; Ozgul, E; Kandemir, CG (Informa UK Limited, 1996-01-01) 2-Substituted epichlorohydrins have been synthesized by starting with 1,2-dichloro acetone and various alkyl and aryl halides via dichlorohydrins followed by cyclization. The reactive 2-substituted epichlorohydrins were subjected to nucleophilic attacking of azide and cyanide ions to afford corresponding beta-azido alcohols and alpha,beta-unsaturated nitriles.
Synthesis of 2,3-disubstituted thiophenes from ketoalkynes Vatansever, Erol Can; Balcı, Metin; Department of Chemistry (2013) Synthesis of thiophene containing compounds are of particular interest in synthetic organic chemistry. Besides the importance for synthetic organic chemistry, thiophene derivatives are used in applied research such as drug synthesis and study of functional materials. In this thesis, a new methodology for developing of 2,3-disubstituted thiophenes was developed. This methodology utilizes readily available compounds in a two-step synthesis to provide a facile access to the 2,3-disubstituted thiophenes. In the...
Generation of acyl anion equivalents from acylphosphonates via phosphonate-phosphate rearrangement: A highly practical method for cross-benzoin reaction Demir, Ayhan Sıtkı; Reis, O; Igdir, AC; Esiringu, I; Eymur, S (American Chemical Society (ACS), 2005-12-09) Acylphosphonates are potent acyl anion precursors that generate acyl anion equivalents under the promotion of cyanide anion via phosphonate-phosphate rearrangement. These anions readily react with aldehydes to provide cross-benzoin products. In this way it is possible to synthesize a variety of aromatic-aromatic, aromatic-aliphatic, and aliphatic-aromatic benzoins. Moreover the reaction of benzoylphosphonate with potent electrophile 2,2,2-trifluoroacetophenone provided the corresponding aldehyde-ketone coup...

Citation Formats

A. S. Demir, O. Reis, and M. Emrullahoglu, “Generation of aryl radicals from arylboronic acids by manganese(III) acetate: Synthesis of biaryls and heterobiaryls,” JOURNAL OF ORGANIC CHEMISTRY, pp. 578–580, 2003, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/58029.