References and Notes
1
Kleemann A.
Engel J.
Kutscher B.
Reichert D. In Pharmaceutical
Substances: Syntheses, Patents, Application
4th
ed.:
Thieme;
Stuttgart:
2001.
See, for example:
2a
Sundermeir M.
Zapf A.
Beller M.
Eur.
J. Inorg. Chem.
2003,
3513
2b
Anderson BA.
Bell EC.
Ginah FO.
Harn NK.
Pagh LM.
Wepsiec JP.
J. Org. Chem.
1998,
63:
8224
2c
Maligres PE.
Waters MS.
Fleitz F.
Askin D.
Tetrahedron
Lett.
1999,
40:
8193
2d
Jin F.
Confalone PN.
Tetrahedron Lett.
2000,
41:
3271
3a
Herrman WA.
Broßmer C.
Öfele K.
Priermeier T.
Beller M.
Fisher H.
Angew. Chem., Int. Ed. Engl.
1995,
34:
1844
3b
Beller M.
Fisher H.
Herrman WA.
Broßmer C.
Angew. Chem., Int.
Ed. Engl.
1995,
34:
1848
3c
Zapf A.
Beller M.
Chem. Eur. J.
2001,
7:
2908
3d
Sundermeier M.
Zapf A.
Mutyala S.
Baumann W.
Sans J.
Weiss S.
Beller M.
Chem. Eur. J.
2003,
9:
1828
3e
Littke A.
Soumeillant M.
Kaltenbach RF.
Cherney RJ.
Tarby CM.
Kiau S.
Org.
Lett.
2007,
9:
1711
4
Gooßen LJ.
Rodriguez N.
Gooßen K.
Angew. Chem. Int. Ed.
2008,
47:
2
For recent examples, see:
5a
Myers AG.
Tanaka D.
Mannion MR.
J. Am. Chem. Soc.
2002,
124:
11250
5b
Hu P.
Kan J.
Su W.
Hong M.
Org. Lett.
2009,
11:
2341
5c
Tanaka D.
Myers AG.
Org. Lett.
2004,
6:
433
For recent examples, see:
6a
Baudoin O.
Angew.
Chem. Int. Ed.
2007,
46:
2
6b
Gooßen LJ.
Rodriguez N.
Lange PP.
Linder C.
Angew.
Chem. Int. Ed.
2009,
48:
1
6c
Becht J.-M.
Catala C.
Le Drian C.
Wagner A.
Org. Lett.
2007,
9:
1781
6d
Gooßen LJ.
Zimmermann B.
Knauber T.
Angew. Chem. Int. Ed.
2008,
47:
7103
7a
Voutchkova A.
Coplin A.
Leadbeater NE.
Crabtree RH.
Chem. Commun.
2008,
6312
7b
Wang C.
Piel I.
Glorius F.
J.
Am. Chem. Soc.
2009,
131:
4194
8a
Gooßen LJ.
Deng G.
Levy LM.
Science
2006,
313:
662
8b
Gooßen LJ.
Rodriguez N.
Melzer B.
Linder C.
Deng G.
Levy LM.
J. Am. Chem. Soc.
2007,
129:
4824
8c
Moon J.
Jeong M.
Nam H.
Ju J.
Moon JH.
Jung HM.
Lee S.
Org.
Lett.
2008,
10:
945
8d
Shang R.
Fu Y.
Li JB.
Zhang SL.
Guo QX.
Liu L.
J. Am. Chem. Soc.
2009,
131:
5738
8e
Shang R.
Fu Y.
Wang Y.
Xu Q.
Yu HZ.
Liu L.
Angew. Chem. Int. Ed.
2009,
48:
9350
9a
Waetzig SR.
Tunge JA.
J. Am. Chem. Soc.
2007,
129:
14860
9b
Fields WH.
Khan AK.
Sabat M.
Chruma JJ.
Org.
Lett.
2008,
10:
5131
9c
Pi SF.
Tang BX.
Li JH.
Liu YL.
Liang Y.
Org.
Lett.
2009,
11:
2309
10a
Bueler CA.
Pearson DE.
Survey of Organic Synthesis
Wiley
Interscience;
New York:
1970.
p.951
10b
Vorbrüggen H.
Tetrahedron Lett.
1968,
13:
1631
11a
Miller CS.
Org. Synth., Coll.
Vol. III
1955,
646
11b
Lücke J.
Winkler RE.
Chimia
1971,
25:
94
11c
Hulkenberg A.
Troost JJ.
Tetrahedron Lett.
1982,
23:
1505
12a
Sekiya A.
Ishikawa N.
Chem.
Lett.
1975,
277
12b
Sundermeier M.
Zapf A.
Mutyala S.
Baumann W.
Sans J.
Weiss S.
Beller M.
Chem. Eur. J.
2003,
9:
1828
13
Sakakibara Y.
Sasaki K.
Okuda F.
Hokimoto A.
Ueda T.
Sakai M.
Takagi K.
Bull. Chem. Soc. Jpn.
2004,
77:
1013
14
Allentoff AJ.
Markus B.
Duelfer T.
Wu A.
Jones L.
Ciszewska G.
Ray T.
J. Labelled
Compd. Radiopharm.
2000,
43:
1075
15
Ellis GP.
Rommey-Alexander TM.
Chem. Rev.
1987,
87:
779
16a
Jin F.
Confalone PN.
Tetrahedron
Lett.
2000,
41:
3271
16b
Ramnauth J.
Bhardwaj N.
Renton P.
Rakhit S.
Maddaford SP.
Synlett
2003,
2237
17
Sundermeier M.
Zapf A.
Beller M.
Angew.
Chem. Int. Ed.
2003,
42:
1661
18
Carr G.
Whittaker D.
J. Chem. Soc., Perkin Trans.
2
1989,
359
19
General Procedure
for the Preparation of Aryl Nitriles 2
Arene carboxylic
acid (250 mg, 1 equiv), Ag2CO3 (3 equiv), and
palladium trifluoroacetate (0.2 equiv) were suspended in DMSO-DMF
(95:5, 5 mL) under air. The reaction mixture is heated at 100 ˚C,
then, cyclohexanone cyanohydrin
(1 equiv) diluted in DMSO-DMF
(95:5, 5 mL) was added dropwise with a syringe pump. The reaction
mixture rapidly turned black, was further heated for 1 h, then was
cooled, poured into EtOAc, and filtered. The filtrate was washed sequentially
with aq NaHCO3 (1 M), H2O and brine, then was
dried over MgSO4, filtered, and concentrated. Chromatography
of the residue on silica gel (EtOAc-heptane) gave the desired
product. Compounds 2a-l are known compounds.
Compound 2m: white solid, mp 69.6 ˚C. ¹H
NMR (400 MHz, CDCl3): δ = 2.47 (s,
3 H), 3.84 (s, 3 H), 3.88 (s, 3 H), 6.30 (s, 1 H), 6.38 (s, 1 H)
ppm.¹³C NMR (100 MHz, CDCl3): δ = 20.81,
55.51, 55.90, 94.67, 95.70, 106.87, 116.05, 145.25, 163.81, 164.51
ppm. IR (NaCl): 2972, 2212, 1606, 1577, 1468, 1425, 1336, 1304,
1238, 1209, 1153, 1095, 1053, 935, 853, 830 cm-¹.
HRMS: m/z calcd for [M + H]+:178.0868;
found:178.0863.
Compound 2n: white
solid, mp 168.8 ˚C. ¹H NMR
(400 MHz, CDCl3): δ = 3.96 (s, 3 H),
3.97 (s, 3 H), 6.46 (s, 1 H), 7.68 (s, 1 H) ppm.¹³C
NMR (100 MHz, CDCl3): δ = 56.28, 56.47,
94.68, 95.68, 102.20, 116.12, 138.78, 160.41, 162.52. IR (NaCl):
2989, 2224, 1595, 1561, 1492, 1471, 1433, 1386, 1317, 1284, 1221,
1161, 1020, 896, 838, 780 cm-¹. HRMS: m/z calcd for [M + Na]+:263.9636;
found:263.9644.
20
Procedure for
the Preparation of 3h
¹³C-Labeled
9-anthracenecarboxylic acid was prepared in two steps. ¹³C-Labeled
9-anthracenecarbonitrile was first prepared from ¹³C-labeled
cyclohexanone cyanohydrin according to the procedure described above.
After purification, the ¹³C-labeled
nitrile was hydrolyzed under basic conditions: ¹³C-labeled
nitrile (1 mmol) was reacted overnight at 80 ˚C
with aq KOH (10 mL, 40% w/w) and abs. EtOH (10
mL). The mixture was acidified to pH 3 (HCl solution) and extracted
by EtOAc. The organic phase was concentrated, and the residue was
purified by reversed-phase chromatography with MeOH-H2O
(70:30) to afford product 3h; mp 212-214 ˚C. ¹H
NMR (400 MHz, CDCl3): δ = 8.61 (s,
1 H), 8.34 (d, 2 H, J = 8.8
Hz), 8.07 (d, 2 H, J = 8.8
Hz), 7.62 (t, 2 H, J = 7.2
Hz), 7.54 (t, 2 H, J = 7.2
Hz) ppm. ¹³C NMR (100 MHz, CDCl3): δ = 171.38
(¹³CO2H), 131.23, 130.96,
129.96, 128.47, 127.68, 126.80, 125.50, 124.96 ppm. IR (KBr): 3200-2700,
2761, 2623, 1680, 1626, 1557, 1523, 1487, 1447, 1425, 1399, 1343,
1319, 1292, 1266, 1254, 1229, 1177, 1154, 1142, 1020, 992, 917,
891, 857, 847, 793, 738, 723, 639, 596, 559, 513 cm-¹.
HRMS: m/z calcd for C14
¹³CH10O2Na:
246.0578; found: 246.0581.
