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

被引：42
|
作者：
Demir, AS [1 ]
Reis, Ö [1 ]
Emrullahoglu, M [1 ]
机构：
[1] Middle E Tech Univ, Dept Chem, TR-06531 Ankara, Turkey
来源：
TETRAHEDRON | 2002年 / 58卷 / 40期
关键词：
arylcoupling; thiophene; furan; manganese(III) acetate;
D O I：
10.1016/S0040-4020(02)01001-3
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：8055 / 8058
页数：4
相关论文
共 10 条
  • [1] Manganese(III) acetate-mediated oxidative coupling of phenylhydrazines with benzene:: a novel method for biaryl coupling
    Demir, AS
    Reis, Ö
    Özgül-Karaaslan, E
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (22): : 3042 - 3045
  • [2] Manganese(III) acetate-mediated oxidative free radical cyclisations
    Hulcoop, DG
    Burton, JW
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 229 : U509 - U509
  • [3] Manganese(III) Acetate-mediated Oxidative Cyclization of α-Methylstyrene and trans-Stilbene with β-Ketosulfones
    Bouhlel, Ahlem
    Curti, Christophe
    Tabele, Clemence
    Vanelle, Patrice
    MOLECULES, 2013, 18 (04): : 4293 - 4307
  • [4] Novel and efficient oxidative biaryl coupling reaction of alkylarenes using a hypervalent iodine(III) reagent
    Tohma, H
    Iwata, M
    Maegawa, T
    Kita, Y
    TETRAHEDRON LETTERS, 2002, 43 (50) : 9241 - 9244
  • [5] [60]Fullerene-fused lactones: Manganese(III) acetate-mediated synthesis and novel reductive ring opening
    Wang, GW
    Li, FB
    Zhang, TH
    ORGANIC LETTERS, 2006, 8 (07) : 1355 - 1358
  • [6] An efficient oxidative coupling method for synthesis of novel diastereomeric biaryl diols derived from estrone
    Feng, Jie
    Yang, Xin-Bin
    Lang, Shuai
    Zhang, Ji
    Yu, Xiao-Qi
    TETRAHEDRON LETTERS, 2013, 54 (04) : 355 - 357
  • [7] Manganese(III) Acetate-Mediated Cyclization of Diarylmethylenecyclopropa[b]naphthalenes: A Method for the Synthesis of 1,2-Benzanthracene Derivatives
    Cao, Jian
    Miao, Maozhong
    Chen, Wanli
    Wu, Luling
    Huang, Xian
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (22): : 9329 - 9337
  • [8] MANGANESE(III) ACETATE-MEDIATED ONE-POT SYNTHESIS OF SOME NOVEL MACROLIDES FROM LONG-CHAIN FATTY-ACIDS
    AHMED, MA
    MUSTAFA, J
    OSMAN, SM
    JOURNAL OF CHEMICAL RESEARCH-S, 1991, (02): : 48 - 49
  • [9] A novel and efficient oxidative biaryl coupling reaction of phenol ether derivatives using a combination of hypervalent iodine(III) reagent and heteropoly acid
    Hamamoto, H
    Anilkumar, G
    Tohma, H
    Kita, Y
    CHEMICAL COMMUNICATIONS, 2002, (05) : 450 - 451
  • [10] A mechanistic study of manganese(III) acetate-mediated phosphonyl group additions to [60]and [70]-fullerenes: the oxidative-ion-transfer mechanism vs. free radical addition
    Tumanskii, Boris L.
    Sabirov, Denis S.
    Lyakhovetsky, Yury I.
    DALTON TRANSACTIONS, 2016, 45 (42) : 16838 - 16849
1