Abstract
Arylations of various quinones with several arylboronic acids have been developed. The reactions proceed readily at ambient temperature using iron(II) oxalate as a catalyst and potassium persulfate as a co-oxidant. The mechanism is presumed to proceed through a nucleophilic radical addition to the quinone with in situ reoxidation of the resulting dihydroquinone.
References
1.
Nowicka B.
, and
Kruk J.
Biochim. Biophys. Acta , 2010 , 1797 , 1587 .
2.
Ferreira I.C.F.R.
,
Vaz J.A.
,
Vasconcelos M.H.
, and
Martins A.
, Minireviews Med. Chem. , 2010 , 10 , 424 .
3.
Dandawate P.R.
,
Vyas A.C.
,
Padhye S.B.
,
Singh M.W.
, and
Baruah J.B.
, Mini-Reviews Med. Chem. , 2010 , 10 , 436 .
4.
Bishop K.J.M.
,
Klajin R.
, and
Grzybowski B.A.
, Angew. Chem. Int. Ed. , 2006 , 45 , 5348 .
5.
Lana E.J.L.
,
Carazza F.
, and
de Oliveira R.A.
, Helv. Chim. Acta , 2004 , 87 , 1825 .
6.
Gan X.
,
Jiang W.
,
Wang W.
, and
Hu L.
, Org. Lett. , 2009 , 11 , 589 .
7.
Molina M.T.
,
Navarro C.
,
Moreno A.
, and
Csákÿ A.G.
Org. Lett. , 2009 , 11 , 4938 .
8.
Demchuk O.M.
, and
Pietrusiewicz K.M.
, Synlett , 2009 , 7 , 1149 .
9.
Luthy M.
,
Darmency V.
, and
Renaud P.
, Eur. J. Org. Chem. , 2011 , 547 .
10.
Fujiwara Y.
,
Domingo V.
,
Seiple I.B.
,
Giantassio R.
,
Bel M.D.
, and
Baran P.S.
, J. Am. Chem. Soc. , 2011 , 133 , 3292 .
11.
Seiple I.B.
,
Su S.
,
Rodriguez R.A.
,
Giantassio R.
,
Fujiwara Y.
,
Sobel A.L.
, and
Baran P.S.
, J. Am. Chem. Soc. , 2010 , 132 , 13194 .
12.
Sun C.-L.
,
Li B.-J.
, and
Shi Z.-J.
, Chem. Rev. , 2011 , 111 , 1293 .
13.
Correa A.
,
Mancheno O.G.
, and
Bolm C.
, Chem. Soc. Rev. , 2008 , 37 , 1108 .
14.
Yoshikai N.
,
Mieczkowski A.
,
Matsumoto A.
,
Ilies L.
, and
Nakamura E.
, J. Am. Chem. Soc. , 2010 , 132 , 5568 .
15.
Wang J.
,
Wang S.
,
Wang G.
,
Zhang J.
, and
Yu X.-Q.
, Chem. Commun. , 2012 , 48 , 11769 .
16.
Komeyama K.
,
Kashihara T.
, and
Takaki K.
, Tetrahedron Lett. , 2013 , 54 , 1084 .
17.
Murahashi S.I.
,
Miyaguchi N.
,
Noda S.
,
Naota T.
,
Fujii A.
,
Inubushi Y.
, and
Komiya N.
, Eur. J. Org. Chem. , 2011 , 5355 .
18.
Yamamoto Y.
, Adv. Synth. Catal. , 2010 , 352 , 478 .
19.
Zhao S.
,
Narang A.
,
Ding X.
, and
Eadon G.
, Chem. Res. Toxicol. , 2004 , 17 , 502 .
20.
Kvalnes D.E.
, J. Am. Chem. Soc. , 1934 , 56 , 2478 .
21.
Cain B.F.
, J. Chem. Soc. , 1961 , 936 .
22.
Irvine S.
,
Kerr W.J.
,
McPherson A.R.
, and
Pearson C.M.
, Tetrahedron , 2008 , 64 , 926 .
