Abstract
We have established the optimal conditions for the Wittig reaction for synthesizing α-bromoacrylates with a high selectivity, and developed a simple and efficient one-pot procedure for preparing various conjugated acetylenic carboxylates in moderate to high yields.
Key words
α-bromoacrylate - conjugated acetylenic carboxylate - aldehyde - Wittig reaction
References and Notes
1a Liu Z.
Larock RC.
Angew. Chem. Int. Ed.
2007,
46:
2535
1b Yavari I.
Souri S.
Sirouspour M.
Djahaniani H.
Synthesis
2006,
3243
1c Armenise D.
De Laurentis N.
Roato A.
Morlacchi F.
J. Heterocycl. Chem.
2006,
43:
1371
1d Raad I.
Terreux R.
Richomme P.
Matera E.-L.
Dumontet C.
Raynaud J.
Guilet D.
Bioorg. Med. Chem.
2006,
14:
6979
1e Rubina M.
Conley M.
Gevorgyan V.
J. Am. Chem. Soc.
2006,
128:
5818
1f Burton RR.
Tam W.
Tetrahedron Lett.
2006,
47:
7185
2a Stefani HA.
Cella R.
Doerr FA.
de Pereira CMP.
Gomes FP.
Zeni G.
Tetrahedron Lett.
2005,
46:
2001
2b Fürst M.
Rück-Braun K.
Synlett
2002,
1991
2c Böttcher A.
Becker H.
Brunner M.
Preiss T.
Henkelmann J.
De Bakker C.
Gleiter R.
J. Chem. Soc., Perkin Trans. 1
1999,
3555
3a Zou G.
Zhu J.
Tang J.
Tetrahedron Lett.
2003,
44:
8709
3b Radhakrishnan U.
Stang PJ.
Org. Lett.
2001,
3:
859
3c Kang S.-K.
Yoon S.-K.
Kim Y.-M.
Org. Lett.
2001,
3:
2697
3d Sakamoto T.
Shiga F.
Yasuhara A.
Uchiyama D.
Kondo Y.
Yamanaka H.
Synthesis
1992,
746
4a Hashmi A.
Stephen K.
Grundl MA.
Nass AR.
Naumann F.
Bats JW.
Bolte M.
Eur. J. Org. Chem.
2001,
4705
4b Newman MS.
Merrill SH.
J. Am. Chem. Soc.
1955,
77:
5549
5a Kobrich G.
Buck P.
In Chemistry of Acetylenes
Viehe HG.
Marcel Dekker;
New York:
1969.
p.99
5b Schuda PF.
Heimann MR.
J. Org. Chem.
1982,
47:
2484
5c Kobrich G.
Angew. Chem., Int. Ed. Engl.
1965,
4:
49
6a Hendrickson JB.
Hussoin MS.
Synthesis
1989,
217
6b Kitazume T.
Ishikawa N.
Chem. Lett.
1980,
9:
1327
7a Barma DK.
Kundu A.
Zhang H.
Mioskowski C.
Falck JR.
J. Am Chem. Soc.
2003,
125:
3218
7b Ramanarayanan GV.
Shukla VG.
Akamanchi KG.
Synlett
2002,
2059
7c Forti L.
Ghelfi F.
Pagnoni UM.
Tetrahedron Lett.
1995,
36:
3023
7d Kowalski CJ.
Weber AE.
Fields KW.
J. Org. Chem.
1982,
47:
5088
7e Dunn GL.
Dipasquo VJ.
Hoover JRE.
J. Org. Chem.
1968,
33:
1454
7f Bordwell FG.
Wellman KM.
J. Org. Chem.
1963,
28:
2544
8a Zhang X.
Qing F.
Yu Y.
J. Org. Chem.
2000,
65:
7075
8b Tago K.
Kogen H.
Tetrahedron
2000,
56:
8825
8c Sano S.
Ando T.
Yokoyama K.
Nagao Y.
Synlett
1998,
777
8d Braun NA.
Buerkle U.
Feth MP.
Klein I.
Spitzner D.
Eur. J. Org. Chem.
1998,
1569
8e Huang Z.-Z.
Wu L.-L.
Zhu L.-S.
Huang X.
Synth. Commun.
1996,
26:
677
8f Zapata A.
Ferrer GF.
Synth. Commun.
1986,
16:
1611
8g Karrenbrock F.
Schaefer HJ.
Tetrahedron Lett.
1979,
2913
8h Chan TH.
Moreland M.
Tetrahedron Lett.
1978,
515
8i Villieras J.
Perriot P.
Normant JF.
Synthesis
1978,
31
8j Denney DB.
Ross ST.
J. Org. Chem.
1962,
27:
998
9 Burton DJ.
Greenwald JR.
Tetrahedron Lett.
1967,
1535
10 Olpp T.
Brückner R.
Synthesis
2004,
2135
11a Mitchell TN. In
Metal -Catalyzed Cross-Coupling Reactions
Diederich F.
Stang PJ.
Wiley-VCH;
Weinheim:
1998.
11b Chemler SR.
Trauner D.
Danishefsky SJ.
Angew. Chem. Int. Ed.
2001,
40:
4544
11c Boudier A.
Bromm LO.
Lotz M.
Knochel P.
Angew. Chem. Int. Ed.
2000,
39:
4414
11d Poli G.
Giambastiani G.
Heumann A.
Tetrahedron
2000,
56:
5959
12a Tanaka K.
Mori H.
Yamamoto M.
Katsumura S.
J. Org. Chem.
2001,
66:
3099
12b Tanaka K.
Katsumura S.
Org. Lett.
2000,
2:
373
12c Tago K.
Kogen H.
Org. Lett.
2000,
2:
1975
12d Trost BM.
Probst GD.
Schoop A.
J. Am. Chem. Soc.
1998,
120:
9228
12e Sai H.
Ogiku T.
Nishitani T.
Hiramatsu H.
Horikawa H.
Iwasaki T.
Synthesis
1995,
582
13a Suzuki I.
Tsuchiya Y.
Shigenaga A.
Nemoto H.
Shibuya M.
Tetrahedron Lett.
2002,
43:
6779
13b Dai W.-M.
Wu A.
Lee MYH.
Lai KW.
Tetrahedron Lett.
2001,
42:
4215
13c Dai W.-M.
Wu J.
Fong KC.
Lee MYH.
Lau CW.
J. Org. Chem.
1999,
64:
5062
14a Nowak I.
Robins MJ.
J. Org. Chem.
2007,
72:
2678
14b Zhang X.
Qing F.-L.
Yu Y.
J. Org. Chem.
2000,
65:
7075
15a Bartsch RA.
Cho BR.
Pugia MJ.
J. Org. Chem.
1987,
52:
5494
15b Lee JG.
Bartsch RA.
J. Am. Chem. Soc.
1979,
101:
228
16
Typical Procedure : To a mixture of Ph3 P (1.31 g, 5 mmol) and Br3 CCO2 Et (0.81 g, 2.5 mmol) in THF (6 mL) under argon was added a solution of p -nitrobenzaldehyde (0.19 g, 1.25 mmol). After heating at reflux for 3 h, the reaction mixture was cooled to r.t. A mixture of NaNH2 (0.78 g, 1.88 mmol) and t -BuOK (0.21 g, 1.88 mmol) in THF (3 mL) was added to the reaction mixture. After stirring at r.t. for 2 h, the mixture was diluted with Et2 O, washed with brine, and dried over anhyd MgSO4 . After evaporation of the solvent, the residue was separated by column chromatography on silica gel (hexane-EtOAc, 9:1) affording the product in 82% yield; mp 122-123 °C (lit.
[3d 1 H NMR (300 MHz, CDCl3 ): δ = 8.31 (d, J = 9.0 Hz, 2 H), 7.78 (d, J = 9.0 Hz, 2 H), 4.37 (q, J = 7.0 Hz, 2 H), 1.38 (t, J = 7.0 Hz, 3 H).
