References and Notes
<A NAME="RW00811ST-1A">1a</A>
Lawrence SA.
Amines:
Synthesis Properties and Application
Cambridge
University Press;
Cambridge:
2004.
<A NAME="RW00811ST-1B">1b</A>
Suwanprasop S.
Nhujak T.
Roengsumran S.
Petsom A.
Ind. Eng. Chem. Res.
2004,
43:
4973
<A NAME="RW00811ST-2A">2a</A>
Gujadhur R.
Venkataraman D.
Kintigh JT.
Tetrahedron Lett.
2001,
42:
4791
<A NAME="RW00811ST-2B">2b</A>
Kelkar AA.
Patil NM.
Chaudhari RV.
Tetrahedron Lett.
2002,
43:
7143
<A NAME="RW00811ST-2C">2c</A>
Zhang H.
Cai Q.
Ma D.
J.
Org. Chem.
2005,
70:
5164
<A NAME="RW00811ST-2D">2d</A>
Rao H.
Fu H.
Jiang Y.
Zhao Y.
J. Org. Chem.
2005,
70:
8107
<A NAME="RW00811ST-2E">2e</A>
Kantam ML.
Venkanna GT.
Sridhar C.
Sreedhar B.
Choudary BM.
J. Org. Chem.
2006,
71:
9522
<A NAME="RW00811ST-2F">2f</A>
Guo X.
Rao H.
Fu H.
Jiang Y.
Zhao Y.
Adv. Synth.
Catal.
2006,
348:
2197
<A NAME="RW00811ST-2G">2g</A>
Rao H.
Jin Y.
Fu H.
Jiang Y.
Zhao Y.
Chem. Eur.
J.
2006,
12:
3636
<A NAME="RW00811ST-2H">2h</A>
Liu Y.
Bai Y.
Zhang J.
Li Y.
Jiao J.
Qi X.
Eur.
J. Org. Chem.
2007,
6084
<A NAME="RW00811ST-2I">2i</A>
Rout L.
Jammi S.
Punniyamurthy T.
Org.
Lett.
2007,
9:
3397
<A NAME="RW00811ST-2J">2j</A>
He C.
Chen H.
Cheng J.
Liu C.
Liu W.
Li Q.
Lei A.
Angew. Chem. Int. Ed.
2008,
47:
6414
<A NAME="RW00811ST-2K">2k</A>
Altman RA.
Anderson KW.
Buchwald SL.
J. Org. Chem.
2008,
73:
5167
<A NAME="RW00811ST-2L">2l</A>
Yang C.-T.
Fu Y.
Huang Y.-B.
Yi J.
Guo
Q.-X.
Liu L.
Angew. Chem. Int. Ed.
2009,
48:
7398
<A NAME="RW00811ST-2M">2m</A>
Lin B.
Liu M.
Ye Z.
Ding J.
Wu H.
Cheng J.
Org. Biomol.
Chem.
2009,
7:
869
<A NAME="RW00811ST-2N">2n</A>
Zhu X.
Su L.
Huang L.
Chen G.
Wang J.
Song H.
Wan Y.
Eur. J. Org. Chem.
2009,
635
<A NAME="RW00811ST-2O">2o</A>
Xie J.
Zhu X.
Huang M.
Meng F.
Chen W.
Wan Y.
Eur.
J. Org. Chem.
2010,
3219
For pertinent reviews on Cu-catalyzed
coupling reactions, see:
<A NAME="RW00811ST-3A">3a</A>
Ley SV.
Thomas AW.
Angew. Chem. Int.
Ed.
2003,
42:
5400
<A NAME="RW00811ST-3B">3b</A>
Beletskaya IP.
Cheprakov AV.
Coord.
Chem. Rev.
2004,
248:
2337
<A NAME="RW00811ST-3C">3c</A>
Evano G.
Blanchard N.
Toumi M.
Chem.
Rev.
2008,
108:
3054
<A NAME="RW00811ST-3D">3d</A>
Ma D.
Cai Q.
Acc. Chem. Res.
2008,
41:
1450
<A NAME="RW00811ST-3E">3e</A>
Monnier F.
Taillefer M.
Angew. Chem. Int. Ed.
2008,
47:
3096
<A NAME="RW00811ST-3F">3f</A>
Monnier F.
Taillefer M.
Angew. Chem. Int. Ed.
2009,
48:
6954
<A NAME="RW00811ST-4A">4a</A>
Wolfe JP.
Buchwald SL.
J. Org. Chem.
1997,
62:
6066
<A NAME="RW00811ST-4B">4b</A>
Li GY.
Zheng G.
Noonan AF.
J.
Org. Chem.
2001,
66:
8677
<A NAME="RW00811ST-4C">4c</A>
Huang X.
Anderson KW.
Zim D.
Jiang L.
Klapars A.
Buchwald SL.
J. Am. Chem. Soc.
2003,
125:
6653
<A NAME="RW00811ST-4D">4d</A>
Urgaonkar S.
Verkade JG.
J. Org. Chem.
2004,
69:
9135
<A NAME="RW00811ST-4E">4e</A>
Hill LL.
Moore LR.
Huang R.
Craciun R.
Vincent AJ.
Dixon DA.
Chou J.
Woltermann CJ.
Shaughnessy KH.
J. Org. Chem.
2006,
71:
5117
<A NAME="RW00811ST-4F">4f</A>
Surry DS.
Buchwald SL.
J.
Am. Chem. Soc.
2007,
129:
10354
<A NAME="RW00811ST-4G">4g</A>
So CM.
Zhou Z.
Lau CP.
Kwong FY.
Angew. Chem. Int. Ed.
2008,
47:
6402
<A NAME="RW00811ST-4H">4h</A>
Fors BP.
Watson DA.
Biscoe MR.
Buchwald
SL.
J.
Am. Chem. Soc.
2008,
130:
13552
<A NAME="RW00811ST-4I">4i</A>
Manolikakes G.
Gavryushin A.
Knochel P.
J.
Org. Chem.
2008,
73:
1429
<A NAME="RW00811ST-4J">4j</A>
Fors BP.
Krattiger P.
Strieter E.
Buchwald
SL.
Org.
Lett.
2008,
10:
3505
<A NAME="RW00811ST-4K">4k</A>
Hill LL.
Smith JM.
Brown WS.
Moore LR.
Guevera P.
Pair ES.
Porter J.
Chou J.
Wolterman CJ.
Craciun R.
Dixon DA.
Shaughnessy KH.
Tetrahedron
2008,
64:
6920
<A NAME="RW00811ST-4L">4l</A>
Fors BP.
Davis NR.
Buchwald SL.
J. Am. Chem. Soc.
2009,
131:
5766
<A NAME="RW00811ST-4M">4m</A>
Ruan J.
Shearer L.
Mo J.
Bacsa J.
Zanotti-Gerosa A.
Hancock F.
Wua X.
Xiao J.
Org. Biomol.
Chem.
2009,
7:
3236
<A NAME="RW00811ST-4N">4n</A>
Komáromia A.
Nováka Z.
Adv.
Synth. Catal.
2010,
352:
1523
For pertinent reviews on Pd-catalyzed
coupling reactions, see:
<A NAME="RW00811ST-5A">5a</A>
Schlummer B.
Scholz U.
Adv. Synth. Catal.
2004,
346:
1599
<A NAME="RW00811ST-5B">5b</A>
Buchwald SL.
Mauger C.
Mignani G.
Scholz U.
Adv. Synth.
Catal.
2006,
348:
23
<A NAME="RW00811ST-5C">5c</A>
Surry DS.
Buchwald SL.
Angew.
Chem. Int. Ed.
2008,
47:
6338
<A NAME="RW00811ST-5D">5d</A>
Hartwig JF.
Acc. Chem. Res.
2008,
41:
1534
<A NAME="RW00811ST-6A">6a</A>
Tamura M.
Kochi JK.
J.
Am. Chem. Soc.
1971,
93:
1487
<A NAME="RW00811ST-6B">6b</A>
Tamura M.
Kochi JK.
Synthesis
1971,
303
<A NAME="RW00811ST-6C">6c</A>
Tamura M.
Kochi JK.
J. Organomet. Chem.
1971,
31:
289
<A NAME="RW00811ST-7A">7a</A>
Plietker B.
Angew. Chem. Int. Ed.
2006,
45:
6053
<A NAME="RW00811ST-7B">7b</A>
Taillefer M.
Xia N.
Ouali A.
Angew.
Chem. Int. Ed.
2007,
46:
934
<A NAME="RW00811ST-7C">7c</A>
Song R.
Deng C.
Xie Y.
Li J.
Tetrahedron Lett.
2007,
48:
7845
<A NAME="RW00811ST-7D">7d</A>
Guo D.
Huang H.
Xu J.
Jiang H.
Liu H.
Org. Lett.
2008,
10:
4513
<A NAME="RW00811ST-7E">7e</A>
Du Y.
Chang J.
Reiner J.
Zhao K.
J. Org. Chem.
2008,
73:
2007
<A NAME="RW00811ST-7F">7f</A>
Wang Z.
Zhang Y.
Fu H.
Jiang Y.
Zhao Y.
Org. Lett.
2008,
10:
1863
<A NAME="RW00811ST-7G">7g</A>
Swapna K.
Kumar AV.
Reddy VP.
Rao KR.
J. Org. Chem.
2009,
74:
7514
<A NAME="RW00811ST-7H">7h</A>
Li P.
Zhang Y.
Wang L.
Chem.
Eur. J.
2009,
15:
2045
<A NAME="RW00811ST-7I">7i</A>
Mao J.
Xie G.
Zhan J.
Hua Q.
Shi D.
Adv. Synth.
Catal.
2009,
351:
1268
<A NAME="RW00811ST-7J">7j</A>
Lee HW.
Chan ASC.
Kwong FY.
Tetrahedron Lett.
2009,
50:
5868
<A NAME="RW00811ST-8A">8a</A>
Wang Z.
Fu H.
Jiang Y.
Zhao Y.
Synlett
2008,
2540
<A NAME="RW00811ST-8B">8b</A>
Guo D.
Huang H.
Zhou Y.
Xu J.
Jiang H.
Chen K.
Liu H.
Green Chem.
2010,
12:
276
<A NAME="RW00811ST-9">9</A>
General Procedure
for the Synthesis of Diaryl Ethers
A Schlenk tube
equipped with a magnetic stir bar was charged with p-toluidine
(2a, 0.75 mmol, 80 mg), K2CO3 (138
mg, 1 mmol), Fe(acac)3 (34.4 mg, 20 mo%), and Cu(OAc)2˙H2O
(20 mg, 20 mol%). Under a nitrogen atmosphere, bromobenzene
(1a, 0.5 mmol, 78.0 mg) was added followed
by dry DMF (0.8 mL). The reaction mixture was then heated in an
oil bath of 135 ˚C. After being stirred at this temperature
for 20 h, the mixture was cooled to r.t. and diluted with Et2O.
The resulting suspension was directly filtered through a pad of
Celite, the filtrate was concentrated, and the crude mixtures were
purified by column chroma-tography on silica gel using PE-EtOAc
solvent mixture as the eluent.
4-Methyl-
N
-phenylaniline
(3a)
¹H NMR (400 MHz, CDCl3): δ = 7.22
(t, J = 7.7
Hz, 2 H), 7.07 (d, J = 8.3
Hz, 2 H), 6.94-7.00 (m, 4 H), 6.87 (t, J = 7.3 Hz,
1 H), 5.58 (br s, 1 H), 2.29 (s, 3 H). ¹³C
NMR (100 MHz, CDCl3): δ = 144.35, 140.68,
131.34, 130.30, 129.75, 120.71, 119.31, 117.26, 21.15. HRMS (EI+): m/z calcd for C13H13N [M+]:
183.1048; found: 183.1051.
Ethyl 1-
p
-Tolyl-1
H
-imidazole-4-carboxylate
(Table 3, Entry 5)
¹H NMR (400
MHz, CDCl3): δ = 7.93 (s, 1 H), 7.82
(s, 1 H), 7.30 (s, 4 H), 4.41 (q, J = 7.1
Hz, 2 H), 2.42 (s, 3 H), 1.41 (t, J = 7.1
Hz, 3 H). ¹³C NMR (75 MHz, CDCl3): δ = 163.25, 138.99,
136.77, 135.30, 134.50, 131.02, 124.56, 122.02, 61.17, 21.481, 14.87.
HRMS (EI+): m/z calcd
for C13H14N2O2 [M+]:
230.1055; found: 230.1058.