Abstract
Herein, we present a method to access a series of 1,5-functionalized
anthracenes through Kumada coupling. All syntheses start from readily
available 1,5-dichloroanthracene. The so-formed anthracenes are
further derivatized to enable, for example, attachment to supramolecular
systems.
Key words
Grignard reaction - Kumada coupling - cross
coupling - anthracene - nickel
References
<A NAME="RT36111SS-1">1 </A>
Fritzsche J.
C.
R. Hebd. Seances Acad. Sci.
1867,
69:
1035
<A NAME="RT36111SS-2A">2a </A>
Becker HD.
Chem. Rev.
1993,
93:
145
<A NAME="RT36111SS-2B">2b </A>
Bouas-Laurent H.
Castellan A.
Desvergne J.-P.
Lapouyade R.
Chem. Soc. Rev.
2000,
29:
43
<A NAME="RT36111SS-2C">2c </A>
Bouas-Laurent H.
Castellan A.
Desvergne J.-P.
Lapouyade R.
Chem. Soc. Rev.
2001,
30:
248
<A NAME="RT36111SS-3A">3a </A>
Zhang G.
Zhang D.
Ziao X.
Ai X.
Zhang J.
Zhu D.
Chem. Eur. J.
2006,
12:
1067
<A NAME="RT36111SS-3B">3b </A>
Kim SK.
Singh NJ.
Kim SJ.
Kim HG.
Kim JK.
Lee JW.
Kim KS.
Yoon J.
Org. Lett.
2003,
5:
2083
<A NAME="RT36111SS-3C">3c </A>
Kim YK.
Lee HN.
Singh NJ.
Choi HJ.
Xue JY.
Kim KS.
Yoon J.
Hyun MH.
J. Org. Chem.
2008,
73:
301
<A NAME="RT36111SS-3D">3d </A>
Nishimura G.
Maehara H.
Shiraishi Y.
Hirai T.
Chem. Eur. J.
2008,
14:
259
<A NAME="RT36111SS-3E">3e </A>
Shirtcliff LD.
Xu H.
Diederich F.
Eur.
J. Org. Chem.
2010,
846
<A NAME="RT36111SS-3F">3f </A>
Kaanumalle LS.
Gibb CLD.
Gibb BC.
Ramamurthy V.
J.
Am. Chem. Soc.
2005,
127:
3674
<A NAME="RT36111SS-3G">3g </A>
Jayaraj N.
Zhao Y.
Parthasarathy A.
Porel M.
Liu RSH.
Ramamurthy V.
Langmuir
2009,
25:
10575
<A NAME="RT36111SS-3H">3h </A>
Tosic O.
Mattay J.
Eur. J. Org. Chem.
2011,
371
<A NAME="RT36111SS-4A">4a </A>
Schäfer C.
Eckel R.
Ros R.
Mattay J.
Anselmetti D.
J. Am. Chem. Soc.
2007,
129:
1488
<A NAME="RT36111SS-4B">4b </A>
Schäfer C.
Strübe F.
Bringmann S.
Mattay J.
Photochem.
Photobiol. Sci.
2008,
7:
1457
<A NAME="RT36111SS-4C">4c </A>
Molard Y.
Bassani DM.
Desvergne J.-P.
Moran N.
Tucker JHR.
J. Org. Chem.
2006,
71:
8523
<A NAME="RT36111SS-4D">4d </A>
Okada M.
Harada A.
Macromolecules
2003,
36:
9701
<A NAME="RT36111SS-4E">4e </A>
Toyota S.
Kuga M.
Takatsu A.
Goichi M.
Iwanaga T.
Chem. Commun.
2008,
1323
<A NAME="RT36111SS-4F">4f </A>
Cao D.
Meier H.
Angew. Chem. Int. Ed.
2001,
40:
186 ; Angew. Chem. 2001 , 113 , 193
<A NAME="RT36111SS-4G">4g </A>
Gassensmith JJ.
Baumes JM.
Eberhard J.
Smith BD.
Chem.
Commun.
2009,
2517
<A NAME="RT36111SS-4H">4h </A>
Gassensmith JJ.
Arunkumar E.
Barr L.
Baumes JM.
DiVittorio KM.
Johnson JR.
Noll BC.
Smith BD.
J.
Am. Chem. Soc.
2007,
129:
15054
<A NAME="RT36111SS-5">5 </A>
Schäfer C.
Herrmann F.
Mattay J.
Beilstein
J. Org. Chem.
2008,
4:
41 ;
doi: 10.3762/bjoc.4.41
<A NAME="RT36111SS-6">6 </A>
Fages F.
Desvergne J.-P.
Frisch I.
Bouas-Laurent H.
J. Chem. Soc.,
Chem. Commun.
1988,
1414
<A NAME="RT36111SS-7A">7a </A>
Toyota S.
Goichi M.
Kotani M.
Angew. Chem. Int. Ed.
2004,
43:
2248 ; Angew. Chem. 2004 , 116 , 2298
<A NAME="RT36111SS-7B">7b </A>
Vögtle F.
Koch H.
Rissanen K.
Chem. Ber.
1992,
125:
2129
<A NAME="RT36111SS-7C">7c </A>
Brettar J.
Gisselbrecht J.-P.
Gross M.
Solladié N.
Chem. Commun.
2001,
733
<A NAME="RT36111SS-7D">7d </A>
Bar AK.
Gole B.
Ghosh S.
Mukherjee PS.
Dalton Trans.
2009,
6701
<A NAME="RT36111SS-7E">7e </A>
Ghosh S.
Chakrabarty R.
Mukherjee PS.
Inorg.
Chem.
2009,
48:
549
<A NAME="RT36111SS-7F">7f </A>
Katz HE.
J. Org. Chem.
1989,
54:
2179
<A NAME="RT36111SS-7G">7g </A>
Kauffman JM.
Synthesis
2001,
197
<A NAME="RT36111SS-7H">7h </A>
Effenberger F.
Heid S.
Merkle R.
Zimmermann P.
Synthesis
1995,
1115
<A NAME="RT36111SS-7I">7i </A>
Yagodkin E.
Douglas CJ.
Tetrahedron Lett.
2010,
51:
3037
<A NAME="RT36111SS-7J">7j </A>
Rein R.
Gross M.
Solladié N.
Chem. Commun.
2004,
1992
<A NAME="RT36111SS-7K">7k </A>
Flamingni L.
Talarico AM.
Ventura B.
Rein R.
Solladié N.
Chem.
Eur. J.
2006,
12:
701
<A NAME="RT36111SS-7L">7l </A>
House HO.
Hrabie JA.
VanDerveer D.
J. Org. Chem.
1986,
51:
921
<A NAME="RT36111SS-7M">7m </A>
Synthesis of 1,5-dichloroanthra-cene
(1 ) is analogous to the described synthesis7l of
1,8-dichloroanthracene.
<A NAME="RT36111SS-8A">8a </A>
Rosen BM.
Quasdorf KW.
Wilson DA.
Zhang N.
Resmerita A.-M.
Garg NK.
Percec V.
Chem.
Rev.
2011,
111:
1346
<A NAME="RT36111SS-8B">8b </A>
Jana R.
Pathak TP.
Sigman MS.
Chem. Rev.
2011,
111:
1417
<A NAME="RT36111SS-9A">9a </A>
Clar E.
Mackay CC.
Tetrahedron
1972,
28:
5049
<A NAME="RT36111SS-9B">9b </A>
Cristol SJ.
Caspar ML.
J.
Org. Chem.
1967,
33:
2020
For examples from numerous reports
in the literature, see:
<A NAME="RT36111SS-10A">10a </A>
Martinez GR.
Garcia F.
Catalani LH.
Cadet J.
Oliveira MCB.
Ronsein GE.
Miyamoto S.
Medeiros MHG.
Di Mascio P.
Tetrahedron
2006,
62:
10762
<A NAME="RT36111SS-10B">10b </A>
Barton DHR.
Hui RAHF.
Lester DJ.
Ley SV.
Tetrahedron Lett.
1979,
3331
<A NAME="RT36111SS-10C">10c </A>
Koeberg-Telder A.
Cerfontain H.
Tetrahedron
Lett.
1974,
3535
<A NAME="RT36111SS-10D">10d </A>
Tanko JM.
Wang Y.
Chem. Commun.
1997,
2387
<A NAME="RT36111SS-11A">11a </A>
Kitagawa K.
Inoue A.
Shinokubo H.
Oshima K.
Angew.
Chem. Int. Ed.
2000,
39:
2481 ; Angew. Chem. 2000 , 112 , 2594
<A NAME="RT36111SS-11B">11b </A>
Inoue A.
Kitagawa K.
Shinikubo H.
Oshima K.
J. Org. Chem.
2001,
66:
4333
<A NAME="RT36111SS-12">12 </A>
Lau SYW.
Hughes G.
O’Shea PD.
Davies IW.
Org. Lett.
2007,
9:
2239
<A NAME="RT36111SS-13">13 </A>
Cashman JR.
Voelker T.
Zhang H.-T.
O’Donnell JM.
J. Med.
Chem.
2009,
52:
1530
<A NAME="RT36111SS-14">14 </A>
Sakata Y.
Toyoda T.
Misumi S.
Tetrahedron
Lett.
1992,
33:
5077
<A NAME="RT36111SS-15">15 </A>
Bringmann S., Brodbeck R., Hartmann
R., Schäfer C., Mattay J. to be published
<A NAME="RT36111SS-16">16 </A>
Palazzott MC,
Rakow NA, and
Wendland MS. inventors; Fluorescent chemical sensor, U.S.
Pat. Appl. Publ. G01N 33/50 20060101
G01N033/50.
<A NAME="RT36111SS-17">17 </A>
Osuka A.
Fujikane D.
Shinmori H.
Kobatake S.
Irie M.
J.
Org. Chem.
2001,
66:
3913