Abstract
1,2-Diaryl-substituted acenaphthylene derivatives were prepared simply via Suzuki-Miyaura coupling in good or excellent yields. By applying this method, acenaphthylene-1,2-bis(p -quinone methide) with two 3,5-di-tert -butyl-4-oxocyclohexadienylidene units, which is a stable deep purple crystalline substance with a very broad absorption in the whole visible region and relatively low reduction potential, was prepared and characterized.
Key words
arenes - chromophores - cross-coupling - quinines - Suzuki reaction
References and Notes
1a Wu Y.-T.
Siegel JS.
Chem. Rev.
2006,
106:
4843
1b Tsefrikas VM.
Scott LT.
Chem. Rev.
2006,
106:
4868
1c Echavarren AM.
Gomez-Lor B.
Gonzalez JJ.
de Frutos O.
Synlett
2003,
585
2a Neudorff WD.
Schulte N.
Lentz D.
Schlüter AD.
Org. Lett.
2001,
3:
3115
2b Gourdon A.
Eur. J. Org. Chem.
1998,
2797
3a Bachmann WE.
Chu EJ.-H.
J. Am. Chem. Soc.
1936,
58:
1118
3b Bartlett PD.
Brown RF.
J. Am. Chem. Soc.
1940,
62:
2927
3c Lai YH.
Chen P.
J. Chem. Soc., Perkin Trans. 2
1989,
1665
3d Lai YH.
Chen P.
Cui YX.
J. Chem. Soc., Perkin Trans. 2
1996,
1655
3e Schank K.
Beck H.
Buschlinger M.
Eder J.
Heisel T.
Pistorius S.
Wagner C.
Helv. Chim. Acta
2000,
83:
801
4a Kurata H.
Tanaka T.
Oda M.
Chem. Lett.
1999,
749
4b Kurata H.
Shimoyama T.
Matsumoto K.
Kawase T.
Oda M.
Bull. Chem. Soc. Jpn.
2001,
74:
1327
4c Kurata H.
Takehara Y.
Kawase T.
Oda M.
Chem. Lett.
2003,
32:
538
4d Kawase T.
Minami Y.
Nishigaki N.
Okano S.
Kurata H.
Oda M.
Angew. Chem. Int. Ed.
2005,
44:
316
4e Kurata H.
Takehara Y.
Matsumoto K.
Kawase T.
Oda M.
Chem. Lett.
2005,
34:
1660
4f Kurata H.
Kim S.
Matsumoto K.
Kawase T.
Oda M.
Chem. Lett.
2007,
36:
386
5a Hassan J.
Sevignon M.
Gozzi C.
Schuz E.
Lemaire M.
Chem. Rev.
2002,
102:
1359
5b Bellina F.
Carpita A.
Rossi R.
Synthesis
2004,
2419
6 4 have been reported: Begum RA.
Sharp PR.
Organometallics
2005,
24:
2670
7 Dyker G.
Merz K.
Oppel IM.
Muth E.
Synlett
2007,
897
8 Trost BM.
Brittelli DR.
J. Org. Chem.
1967,
32:
2620
9 In agreement with literature reports,
[3c 7 1 H NMR spectra of 1e and 1f show the presence of 1:1 mixtures of rotational isomers.
10 5 was prepared by reaction of 4-bromo-2,6-di-tert -butylphenol with tert -BuLi (3 equiv) and subsequently with tri(isopropoxy)borane (4 equiv). Compound 5 was obtained as a mixture with the corresponding boroxane formed by dehydration.Compound 5 : white powder. 1 H NMR (270 MHz, CDCl3 ): δ = 7.54 (s, 2 H), 5.48 (s, 1 H), 4.40 (s, 2 H), 1.47 (s 18 H).The boroxane: white powder. 1 H NMR (270 MHz, CDCl3 ): δ = 8.10 (s, 6 H), 5.59 (s, 3 H), 1.53 (s, 54 H). The trimethylsilyl-protected derivative of 5 was synthesized by Satoh et al.: Satoh Y.
Shi C.
Synthesis
1994,
1146
11 Kurata H.
Tanaka T.
Sauchi T.
Kawase T.
Oda M.
Chem. Lett.
1997,
947
12 Crystallographic data of 3 : C40 H46 O2 , M = 558.80, monoclinic, P 21 /c , a = 21.040 (9), b = 13.717 (6), c = 24.053 (10) Å, β = 103.24 (4)°, V = 6757 (17) Å3 , Z = 8, D
c = 1.098 g cm-3 , 64264 reflections measured, 15373 unique (R
int = 0.145) used in refinement. R1 = 0.058 [I > 2σ (I )], wR = 0.155 (all data). T = 200 K. X-ray data have been deposited at the Cambridge Crystallographic Data Centre (CCDC-649872). Copies of the data can be obtained free of charge at www.ccdc.cam.uk/data_request/cif or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ [fax: +44 (1223)336033; e-mail: deposit@ccdc.cam.ac.uk].
13 Variable-temperature NMR measurement of 3 was performed in a bromobenzene-d
5 solution. The coalescence temperature of the tert -butyl signals was 78 ± 3 °C.
14 Measurements were carried out in DMF solution at r.t. using a glassy carbon electrode with tetrabutylammonium perchlorate as the supporting electrolyte.
15 Richter F.
J. Org. Chem.
1960,
25:
356
