References and Notes
-
1a
Gul W.
Hamann MT.
Life
Sci.
2005,
78:
442
-
1b
Pindur U.
Lemster T.
Curr. Med. Chem.
2001,
8:
1681
-
1c
Fan H.
Peng J.
Hamann MT.
Hu J.-F.
Chem. Rev.
2008,
108:
264
-
1d
Gupton JT.
Topics in Heterocyclic Chemistry
Vol.
2:
Lee M.
Springer;
Berlin / Heidelberg:
2006.
p.53-92
-
1e
Galm U.
Hager MH.
Van Lanen SG.
Ju J.
Thorson JS.
Shen B.
Chem. Rev.
2005,
105:
739
-
1f
Lisowski V.
Léonce S.
Kraus-Berthier L.
Santos JS.-d O.
Pierré A.
Atassi G.
Caignard D.-H.
Renard P.
Rault S.
J. Med. Chem.
2004,
47:
1448
-
2a
Abbiati G.
Casoni A.
Canevari V.
Nava D.
Rossi E.
Org. Lett.
2006,
8:
4839
-
2b
Hwang SJ.
Cho SH.
Chang S.
J. Am. Chem. Soc.
2008,
130:
16158
-
2c
Campo MA.
Larock RC.
J.
Org. Chem.
2002,
67:
5616
-
2d
Ren h.
Knochel P.
Angew. Chem. Int. Ed.
2006,
45:
3462
-
For reviews on the use of arynes
in organic synthesis, see:
-
3a
Peña D.
Pérez D.
Guitián E.
Angew.
Chem. Int. Ed.
2006,
45:
3579
-
3b
Kessar SV.
Comprehensive Organic Synthesis
Vol.
4:
Trost BM.
Fleming I.
Pergamon Press;
New York:
1991.
p.483-515
-
4a For
the application of arynes in total synthesis, see: Allan KA.
Stoltz BM.
J.
Am. Chem. Soc.
2008,
130:
17270
-
4b
Tambar UK.
Ebner DC.
Stoltz BM.
J. Am. Chem. Soc.
2006,
128:
11752
-
4c
Sato Y.
Tamura T.
Mori M.
Angew.
Chem. Int. Ed.
2004,
43:
2436
-
For selected examples of aryne reactions
with nucleophiles, see:
-
5a
Liu ZJ.
Larock RC.
J. Org. Chem.
2006,
71:
3198 ; and references therein
-
5b
Yoshida H.
Watanabe M.
Ohshita J.
Kunai A.
Chem. Commun.
2005,
3292
-
5c
Tambar UK.
Stoltz BM.
J.
Am. Chem. Soc.
2005,
127:
5340
-
5d
Gilmore CD.
Allan KM.
Stoltz BM.
J. Am. Chem. Soc.
2008,
130:
1558
-
5e
Bronner SM.
Bahnck KB.
Garg NK.
Org. Lett.
2009,
11:
1007
- 6
Zhao J.
Larock RC.
J. Org. Chem.
2007,
72:
583
-
7a
Ramtohul YK.
Chartrand A.
Org.
Lett.
2007,
9:
1029
-
7b
Blackburn T.
Ramtohul YK.
Synlett
2008,
1159
- 8
Bailey AS.
Scott PW.
Vandrevala MH.
J. Chem. Soc., Perkin Trans. 1
1980,
97
- 9
Yoshihara T.
Druzhinin SI.
Zachariasse KA.
J. Am. Chem. Soc.
2004,
126:
8535
- 10
Himeshima Y.
Sonoda T.
Kobayashi H.
Chem.
Lett.
1983,
1211
-
11a
Yoshida H.
Shirakawa E.
Honda Y.
Hiyama T.
Angew.
Chem. Int. Ed.
2002,
41:
3247
-
11b
Yoshida H.
Fukushima H.
Ohshita J.
Kunai A.
J. Am. Chem. Soc.
2006,
128:
11040
12
Representative
Experimental Procedure - 5
H
-Indolo[1,2-
a
]indol-5-one (10a)
To
a solution of ethyl 1H-indole-2-carboxylate 9a (76 mg, 0.40 mmol) and TMAF (94 mg,
1.0 mmol) in THF (4 mL) was added 2-(trimethylsilyl)phenyl trifluoromethane-sulfonate
(2a, 107 µL, 0.44 mmol) in an
oven-dried 8 mL glass vial. The reaction mixture was stirred at
r.t. for 1 h, monitored by TLC. The solvent was evaporated, the
residue was diluted with H2O (2 mL) and extracted with
CH2Cl2 (3 × 2 mL;
the organic phase was separated using an organic phase separator
cartridge). The solvent was evaporated and the product was purified
by Combi-flash (ISCO) on silica gel column (10 g) using a gradient
elution of 0-2% EtOAc-hexanes over 3
min, followed by 2-4% EtOAc-hexanes over 25
min) to afford the title product (66 mg, 75% yield) as
a solid. ¹H NMR (500 MHz, acetone-d
6): δ = 7.80
(d, 1 H, J = 8.4
Hz), 7.74 (d, 1 H, J = 8.1
Hz), 7.70 (d, 1 H, J = 7.9 Hz),
7.66-7.60 (m, 2 H), 7.50-7.44 (m, 1 H), 7.21 (s,
1 H), 7.19 (d, 1 H, J = 7.3
Hz), 7.18-7.13 (m, 1 H). ¹³C
NMR (126 MHz, acetone-d
6): δ = 181.5,
146.3, 136.7, 136.5, 135.0, 133.6, 130.0, 128.9, 125.7, 125.4, 124.9,
122.9, 112.8, 112.5, 108.0. HRMS (ESI, MH+): m/z calcd for C15H10NO: 220.0757;
found: 220.0755.