References
Reviews:
1a
Johnson CR.
Aldrichimica Acta
1985,
18:
3
1b
Johnson CR.
Acc. Chem. Res.
1973,
6:
341
1c
Pyne SG.
Sulfur Rep.
1992,
12:
57
1d
Reggelin M.
Zur C.
Synthesis
2000,
1
Selected examples:
2a
Pyne SG.
Dong Z.
Skelton BW.
White AW.
J. Org. Chem.
1997,
62:
2337
2b
Reggelin M.
Heinrich T.
Angew. Chem. Int. Ed.
1998,
37:
2883 ; Angew. Chem. 1998, 110, 3005
2c
Bosshammer S.
Gais H.-J.
Synthesis
1998,
919
2d
Paquette LA.
Gao Z.
Ni Z.
Smith GF.
J. Am. Chem. Soc.
1998,
120:
2543
2e
Harmata M.
Kahraman M.
Jones DE.
Pavri N.
Weatherwax SE.
Tetrahedron
1998,
54:
9995
3a
Bolm C.
Felder M.
Müller J.
Synlett
1992,
439
3b
Bolm C.
Felder M.
Tetrahedron Lett.
1993,
34:
6041
3c
Bolm C.
Müller J.
Schlingloff G.
Zehnder M.
Neuburger M.
J. Chem. Soc., Chem. Commun.
1993,
182
3d
Bolm C.
Seger A.
Felder M.
Tetrahedron Lett.
1993,
34:
8079
3e
Bolm C.
Felder M.
Synlett
1994,
655
3f
Bolm C.
Müller P.
Tetrahedron Lett.
1995,
36:
1625
3g
Bolm C.
Müller P.
Acta Chem. Scand.
1996,
50:
305
4a
Bolm C.
Kahmann JD.
Moll G.
Tetrahedron Lett.
1997,
38:
1169
4b
Bolm C.
Moll G.
Kahmann JD.
Chem.-Eur. J.
2001,
7:
1118
4c
Bolm C.
Müller D.
Hackenberger CHP.
Org. Lett.
2002,
4:
893
5a
Bolm C.
Hildebrand JP.
Tetrahedron Lett.
1998,
39:
5731
5b
Bolm C.
Hildebrand JP.
J. Org. Chem.
2000,
65:
169
5c
Bolm C.
Hildebrand JP.
Rudolph J.
Synthesis
2000,
911
6
Bolm C.
SimiÊ O.
J. Am. Chem. Soc.
2001,
123:
3830
7a
Bolm C.
SimiÊ O.
Martin M.
Synlett
2001,
1878
7b For the use of a related compound, see also: Harmata M.
Ghosh SK.
Org. Lett.
2001,
3:
3321
8 Bolm, C.; Martin, M.; SimiÊ, O.; Verrucci, M., submitted for publication.
9 In a typical experiment [Pd2(dba)3] (36.0 mg, 0.04 mmol) and rac-BINAP (50.0 mg, 0.08 mmol) were dissolved in 20 mL of toluene under an argon atmosphere and refluxed for 10 min. After cooling of the resulting red solution to room temperature, NaO-tBu (384 mg, 4.06 mmol), sulfoximine 1a (776.0 mg, 5.0 mmol), and 2,2′-dibromobiphenyl (312.0 mg, 1.0 mmol) were added and stirring was continued under reflux for an additional 20 h. The suspension was diluted with diethyl ether at room temperature and filtered through a plug of celite. After removing the volatile compounds, the product was directly purified by column chromatography (silica, pentane-ethyl acetate 3:1, Rf = 0.49) furnishing 7a (300 mg, 0.98 mmol, 98%) as a colorless solid, which could be crystallized in ethyl acetate. Mp: 229 °C; [α]D = +62.6
(c = 1, CHCl3). 1H NMR (400 MHz, CDCl3): δ 4.27 (d, J = 15 Hz, 1 H, CH
a
Hb), 4.44 (d, J = 15 Hz, 1 H, CHa
H
b
), 6.68 (d, J = 8 Hz, 1 H, CH
aryl
), 7.15-7.65 (m, 13 H, CH
aryl
).
13C NMR (100 MHz, CDCl3): δ 58.5, 123.3, 127.0, 127.8, 128.4, 128.7, 129.1, 129.7, 129.8, 130.1, 133.5, 135.7, 140.0, 142.3. MS: m/z (%) 305 (M+, 24), 180(100), 152(28). IR (KBr): 685, 724, 768, 782, 810, 872, 995, 1018, 1026, 1109, 1144, 1176, 1206, 1240, 1258, 1281, 1434, 1445, 1475, 1592, 2906, 2972, 3054, 3099 cm-1. Anal. calcd for C19H15NOS: C, 74.73; H, 4.95; N, 4.59; found: C, 74.76;
H, 5.06; N, 4.54.
10 Unless indicated otherwise, [Pd2(dba)3] was used as the catalyst.
11
Lee S.
Hartwig JF.
J. Org. Chem.
2001,
66:
3402
For a selection of recent Pd-catalyzed arylations of CH-acidic substrates, see:
12a
Culkin DA.
Hartwig JF.
J. Am. Chem. Soc.
2001,
123:
5816
12b
Lee S.
Beare NA.
Hartwig JF.
J. Am. Chem. Soc.
2001,
123:
8410
12c
Stauffer SR.
Beare NA.
Stambuli JP.
Hartwig JF.
J. Am. Chem. Soc.
2001,
123:
4641
12d
Gaertzen O.
Buchwald SL.
J. Org. Chem.
2002,
67:
465
12e
Moradi WA.
Buchwald SL.
J. Am. Chem. Soc.
2001,
123:
7996
12f
Vogl EM.
Buchwald SL.
J. Org. Chem.
2002,
67:
106
12g
Hamada T.
Chieffi A.
Åhman J.
Buchwald SL.
J. Am. Chem. Soc.
2002,
124:
1261
12h
Honda T.
Namiki H.
Satoh F.
Org. Lett.
2001,
3:
631
13 Isolated 1-bromo-2-N-[S-methyl-S-phenylsulfonimidoyl]-benzene also did not cyclize when subjected to the typical coupling conditions described in ref.
[9]
14
Harmata M.
Pavri N.
Angew. Chem. Int. Ed.
1999,
38:
2419
