Manganese(III) acetate-mediated oxidative coupling of phenylhydrazines with furan and thiophene: a novel method for hetero biaryl coupling

Date

2002-09-30

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

257
views

0
downloads

A convenient new method for the arylation of furan and thiophene with arylhydrazine and manganese(III) acetate is described. Oxidation of arylhydrazines with Mn(III) acetate in furan or thiophene affords the corresponding 2-aryl-substituted furans and thiophenes in good yield using commercially available materials; access to 2-substituted heterobiaryls works selectively, and coupling occurs with loss of the hydrazine moiety.

Subject Keywords

Organic Chemistry, Biochemistry, Drug Discovery

URI

https://hdl.handle.net/11511/57696

Journal

TETRAHEDRON

DOI

https://doi.org/10.1016/s0040-4020(02)01001-3

Collections

Department of Chemistry, Article

Suggestions

OpenMETU
Core

Indium triflate-catalyzed coupling of indoles with acyl phosphonates: synthesis of bis(indolyl)methane phosphonates Dasbasi, Teslima; Polat-Cakir, Sidika; Abdullah, Meysun; Demir, Ayhan Sıtkı (Elsevier BV, 2011-05-13) The coupling reaction of N-methylindole with alkyl and aryl phosphonate is described. The reaction works in the presence of 10 mol % of indium triflate and furnished bis(indolyl)methane phosphonates in good yield and high selectivity.
Highly efficient and selective olefination of acyl phosphonates with ethyl diazoacetate catalyzed by a cobalt(II) porphyrin complex Erturk, Erkan; Demir, Ayhan Sıtkı (Elsevier BV, 2008-08-04) The cobalt(II) porphyrin complex (CoTPP) was found to be an efficient catalyst for the Wittig type olefination of acyl phosphonates with ethyl diazoacetate (EDA) in the presence of triphenylphosphine (Ph(3)P). By using this one pot methodology under mild conditions, densely functionalized vinyl phosphonates were obtained in high yields and high E/Z selectivities in relatively short reaction times. A rather broad substrate spectrum and steric influence on the reaction rate were observed.
Manganese(III) acetate mediated oxidative coupling of phenylhdrazines with furan and thiophene Emrullahoğlu, Mustafa; Demir, Ayhan Sıtkı; Department of Chemistry (2003) A convenient new method for the arylation of furan and thiophene with arylhydrazine and manganese(III) acetate is described. Oxidation of arylhydrazines with Mn(III) acetate in furan or thiophene affords the corresponding 2-aryl-substituted furans and thiophenes in good yield using commercially available materials; access to 2-substituted heterobiaryls works selectively, and coupling occurs with loss of the hydrazine moiety.
Manganese(III) acetate-mediated synthesis of biaryls under microwave irradiation Demir, Ayhan Sıtkı; Findik, Hamide; SAYGILI, NEZİRE; Subasi, N. Tuna (Elsevier BV, 2010-02-06) Manganese(Ill) acetate (Mn(OAc)(3))-mediated synthesis of biaryls and heterobiaryls starting from arylboronic acid was developed under microwave irradiation in high yields Microwaves were also used for the synthesis of Mn(OAc)(3) from KMnO4 and acetic acid Additional irradiation of this in situ generated Mn(OAc)3 with arylboronic acids, which in turn furnished the biaryls in high yields In a one pot reaction This IS superior from the point of view of yield, short reaction time, sensitive functional group to...
Manganese(III) acetate promoted acetoxylation of various α,β-unsaturated cyclopentanones Tanyeli, Cihangir; Turkut, Engin; SEZEN, Bengü (Elsevier BV, 2003-02-10) We describe the results of manganese(III) acetate based regioselective oxidation of various alpha,beta-unsaturated cyclopentanones leading to alpha'-acetoxy alpha,beta-unsaturated cyclopentanones in good yields. Products due to monophenyl and diphenyl substituted dimerization have been identified as byproducts of the reaction.

Citation Formats

A. S. Demir, O. Reis, and M. Emrullahoglu, “Manganese(III) acetate-mediated oxidative coupling of phenylhydrazines with furan and thiophene: a novel method for hetero biaryl coupling,” TETRAHEDRON, pp. 8055–8058, 2002, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/57696.