-
2
-
-
77950294229
-
-
Also see ref 8 for other medicinal uses of sulfonamides.
-
(b) Also see ref 8 for other medicinal uses of sulfonamides.
-
-
-
-
4
-
-
35848967589
-
-
Paladium catalyst: (a) Ikawa, T.; Barder, T. E.; Biscoe, M. R.; Buchwald, S. L. J. Am. Chem. Soc. 2007, 129, 13001-13007.
-
(2007)
J. Am. Chem. Soc.
, vol.129
, pp. 13001-13007
-
-
Ikawa, T.1
Barder, T.E.2
Biscoe, M.R.3
Buchwald, S.L.4
-
5
-
-
77950249101
-
-
(b) Fors, B. P.; Dooleweerdt, K.; Zeng, Q.; Buchwald, S. L. Tetrahedron 2006, 62, 6042-6049.
-
(2006)
Tetrahedron
, vol.62
, pp. 6042-6049
-
-
Fors, B.P.1
Dooleweerdt, K.2
Zeng, Q.3
Buchwald, S.L.4
-
6
-
-
0034794463
-
-
(c) Klapars, A.; Antilla, J. C.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7727-7729.
-
(2001)
J. Am. Chem. Soc.
, vol.123
, pp. 7727-7729
-
-
Klapars, A.1
Antilla, J.C.2
Huang, X.3
Buchwald, S.L.4
-
7
-
-
0037178121
-
-
(d) Klapars, A.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 7421-7428.
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 7421-7428
-
-
Klapars, A.1
Huang, X.2
Buchwald, S.L.3
-
8
-
-
77950199825
-
-
(e) Enguehard-Gueiffier, C.; Thery, I.; Gueiffier, A.; Buchwald, S. L. Tetrahedron 2009, 65, 6576-6583.
-
(2009)
Tetrahedron
, vol.65
, pp. 6576-6583
-
-
Enguehard-Gueiffier, C.1
Thery, I.2
Gueiffier, A.3
Buchwald, S.L.4
-
9
-
-
0344496782
-
-
(a) Burton, G.; Cao, P.; Li, G.; Rivera, R. Org. Lett. 2003, 23, 4373-4376.
-
(2003)
Org. Lett.
, vol.23
, pp. 4373-4376
-
-
Burton, G.1
Cao, P.2
Li, G.3
Rivera, R.4
-
10
-
-
1642603915
-
-
(b) Steinhuebel, D.; Palucki, M.; Askin, D.; Dolling, U. Tetrahedron Lett. 2004, 45, 3305-3307.
-
(2004)
Tetrahedron Lett.
, vol.45
, pp. 3305-3307
-
-
Steinhuebel, D.1
Palucki, M.2
Askin, D.3
Dolling, U.4
-
11
-
-
45449118071
-
-
(c) Anjanappa, P.; Mullick, D.; Selvakumar, K.; Sivakumar, M. Tetrahedron Lett. 2008, 49, 4585-4587.
-
(2008)
Tetrahedron Lett.
, vol.49
, pp. 4585-4587
-
-
Anjanappa, P.1
Mullick, D.2
Selvakumar, K.3
Sivakumar, M.4
-
12
-
-
0032492942
-
-
For the coupling between aryl boronic acids and sulfonamides see: (a) Chan, D. M. T.; Monaco, K. L.; Wang, R.-P.; Winters, M. P. Tetrahedron Lett. 1998, 39, 2933-2936.
-
(1998)
Tetrahedron Lett.
, vol.39
, pp. 2933-2936
-
-
Chan, D.M.T.1
Monaco, K.L.2
Wang, R.-P.3
Winters, M.P.4
-
14
-
-
0035858723
-
-
For the coupling of aryl halides and sulfonamides under the classic Goldberg reaction conditions see
-
(c) Lam, P. Y. S.; Vincent, G.; Clark, C. G.; Deudon, S.; Jadhav, P. K. Tetrahedron Lett. 2001, 42, 3415-3418. For the coupling of aryl halides and sulfonamides under the classic Goldberg reaction conditions see:
-
(2001)
Tetrahedron Lett.
, vol.42
, pp. 3415-3418
-
-
Lam, P.Y.S.1
Vincent, G.2
Clark, C.G.3
Deudon, S.4
Jadhav, P.K.5
-
15
-
-
0037436943
-
-
For examples of catalytic coupling of aryl halides and sulfonamides
-
(d) He, H.; Wu, Y.-J. Tetrahedron Lett. 2003, 44, 3385-3386. For examples of catalytic coupling of aryl halides and sulfonamides
-
(2003)
Tetrahedron Lett.
, vol.44
, pp. 3385-3386
-
-
He, H.1
Wu, Y.-J.2
-
16
-
-
1242270595
-
-
see: (e) Deng, W.; Wang, Y.-.F.; Zou, Y.; Liu, L.; Guo, Q.-X. Tetrahedron Lett. 2004, 45, 2311-2315.
-
(2004)
Tetrahedron Lett.
, vol.45
, pp. 2311-2315
-
-
Deng, W.1
Wang, Y.-F.2
Zou, Y.3
Liu, L.4
Guo, Q.-X.5
-
17
-
-
25444455340
-
-
(f) Deng, W.; Liu, L.; Zhang, C.; Liu, M.; Guo, Q.-X. Tetrahedron Lett. 2005, 46, 7295-7298.
-
(2005)
Tetrahedron Lett.
, vol.46
, pp. 7295-7298
-
-
Deng, W.1
Liu, L.2
Zhang, C.3
Liu, M.4
Guo, Q.-X.5
-
18
-
-
71049189682
-
-
During the course of the preparation of this manuscript, the coupling of pyridine derivatives and sulfonamides was repotted: Han, X. Tetrahedron Lett. 2010, 51, 360-362.
-
(2010)
Tetrahedron Lett.
, vol.51
, pp. 360-362
-
-
Han, X.1
-
19
-
-
0034738131
-
-
For an example of product inhibition associated with the use of primary sulfonamides
-
For examples of use of 2-aminopyridine as ligands in copper catalysis, see: (a) Fagan, P. J.; Hauptman, E.; Shapiro, R.; Casalnuovo, A. J. Am. Chem. Soc. 2000, 122, 5043-5505 For an example of product inhibition associated with the use of primary sulfonamides see:
-
(2000)
J. Am. Chem. Soc.
, vol.122
, pp. 5043-5505
-
-
Fagan, P.J.1
Hauptman, E.2
Shapiro, R.3
Casalnuovo, A.4
-
20
-
-
33744945513
-
-
For an example of sulfonamide chromium ligand
-
(b) Toto, P.; Gesquiere, J.-C.; Cousaert, N.; Deprez, B.; Willand, N. Tetrahedron Lett. 2006, 47, 4973-5497 For an example of sulfonamide chromium ligand see:
-
(2006)
Tetrahedron Lett.
, vol.47
, pp. 4973-5497
-
-
Toto, P.1
Gesquiere, J.-C.2
Cousaert, N.3
Deprez, B.4
Willand, N.5
-
21
-
-
70450191110
-
-
(c) Liu, X.; Henderson, J. A.; Sasaki, T.; Kishi, Y. J. Am. Chem. Soc. 2009, 131, 16678-16680.
-
(2009)
J. Am. Chem. Soc.
, vol.131
, pp. 16678-16680
-
-
Liu, X.1
Henderson, J.A.2
Sasaki, T.3
Kishi, Y.4
-
22
-
-
14844349847
-
-
CuI as additives in the Hiyama and Suzuki cross-coupling of 2-borono and trimediylsilane pyridine, see: (a) Pierrat, P.; Gros, P.; Fort, Y. Org. Lett. 2005, 7, 697-700.
-
(2005)
Org. Lett.
, vol.7
, pp. 697-700
-
-
Pierrat, P.1
Gros, P.2
Fort, Y.3
-
23
-
-
36749034246
-
-
(b) Jones, N. A.; Antoon, J. W.; Bowie, A. L., Jr.; Borak, J. B.; Stevens, E. P. J. Heterocycl. Chem. 2007, 44, 363-367.
-
(2007)
J. Heterocycl. Chem.
, vol.44
, pp. 363-367
-
-
Jones, N.A.1
Antoon, J.W.2
Bowie Jr.3
, A.L.4
Borak, J.B.5
Stevens, E.P.6
-
24
-
-
61449159817
-
-
(c) Deng, J. Z.; Paone, D. V.; Ginetti, A. T.; Kurihara, H.; Dreher, S. D.; Weissman, S. A.; Stauffer, S. R.; Burgey, C. S. Org. Lett. 2009, 11, 345-347.
-
(2009)
Org. Lett.
, vol.11
, pp. 345-347
-
-
Deng, J.Z.1
Paone, D.V.2
Ginetti, A.T.3
Kurihara, H.4
Dreher, S.D.5
Weissman, S.A.6
Stauffer, S.R.7
Burgey, C.S.8
-
26
-
-
70349786460
-
-
For recent reviews on copper catalysis, see: (a) Monnier, F.; Taillefer, M. Angew. Chem., Int. Ed. 2009, 48, 6954-6971.
-
(2009)
Angew. Chem., Int. Ed.
, vol.48
, pp. 6954-6971
-
-
Monnier, F.1
Taillefer, M.2
-
27
-
-
41149131770
-
-
(b) Canil, M.; SanMartin, R.; Dominguez, E. Chem. Soc. Rev. 2008, 37, 639-647.
-
(2008)
Chem. Soc. Rev.
, vol.37
, pp. 639-647
-
-
Canil, M.1
Sanmartin, R.2
Dominguez, E.3
-
29
-
-
34548296982
-
-
(d) Kienle, M.; Dubbaka, S. R.; Brade, K.; Knochel, P. Eur. J. Org. Chem. 2007, 4166-4176.
-
(2007)
Eur. J. Org. Chem.
, pp. 4166-4176
-
-
Kienle, M.1
Dubbaka, S.R.2
Brade, K.3
Knochel, P.4
-
33
-
-
0345708168
-
-
(g) Ley, S. V.; Thomas, A. W. Angew. Chem., Int. Ed. 2003, 42, 5400-5449.
-
(2003)
Angew. Chem., Int. Ed.
, vol.42
, pp. 5400-5449
-
-
Ley, S.V.1
Thomas, A.W.2
-
35
-
-
77950258220
-
-
The screening results are summarized in Table 1 in the SI.
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The screening results are summarized in Table 1 in the SI.
-
-
-
-
36
-
-
0141854366
-
-
Ma, D. W.; Cai, Q.; Zhang, H. Org. Lett. 2003, 5, 2453-2455.
-
(2003)
Org. Lett.
, vol.5
, pp. 2453-2455
-
-
Ma, D.W.1
Cai, Q.2
Zhang, H.3
-
37
-
-
0037009958
-
-
Antilla, J. C.; Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 11684-11688.
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 11684-11688
-
-
Antilla, J.C.1
Klapars, A.2
Buchwald, S.L.3
-
38
-
-
0033515805
-
-
(a) Kiyomori, A.; Marcoux, J.-F.; .Buchwald, S. L. Tetrahedron Lett. 1999, 40, 2657-2660.
-
(1999)
Tetrahedron Lett.
, vol.40
, pp. 2657-2660
-
-
Kiyomori, A.1
Marcoux, J.-F.2
Buchwald, S.L.3
-
40
-
-
46849092613
-
-
Altman, R. A.; Anderson, K. W.; Buchwald, S. L. J. Org. Chem. 2008, 73, 5167-5169.
-
(2008)
J. Org. Chem.
, vol.73
, pp. 5167-5169
-
-
Altman, R.A.1
Anderson, K.W.2
Buchwald, S.L.3
-
41
-
-
59049094555
-
-
Verrna, A. K.; Kesharwani, T.; Singh, J.; Tandon, V.; Larock, R. C. Angew. Chem., Int. Ed. 2009, 48, 1138-1143.
-
(2009)
Angew. Chem., Int. Ed.
, vol.48
, pp. 1138-1143
-
-
Verrna, A.K.1
Kesharwani, T.2
Singh, J.3
Tandon, V.4
Larock, R.C.5
-
42
-
-
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-
Typical experimental procedure: A dry vial was cooled to it under nitrogen, and was charged with copper(I) iodide (43.0 mg, 0.23 mmol), potassium carbonate (4.15 mg, 3.0 mmol), and p-toluene sulfonamide (257 mg, 1.50 mmol). Dry DMF (10 mL) was added, followed by ligand 1 (0.071 mL, 0.45 mmol) and 2-bromopyridine (286 mg, 1.80 mmol). The resulting blue suspension was stirred at it for 5 min, then heated to 100 °C for 16 h. The reaction mixture was then cooled to it, diluted with ethyl acetate (75 mL), then transferred to a separatory funnel and washed with 10% aqueous ammonium chloride. The aqueous phase was extracted with ethyl acetate (3 times 60 mL). The combined organic phases were washed with water (3 times 75 mL) and brine then dried over magnesium sulfate. All the volatiles were evaporated, and the resulting residue was purified by silica gel chromatography with a DCM/MeOH gradient.
-
Typical experimental procedure: A dry vial was cooled to it under nitrogen, and was charged with copper(I) iodide (43.0 mg, 0.23 mmol), potassium carbonate (4.15 mg, 3.0 mmol), and p-toluene sulfonamide (257 mg, 1.50 mmol). Dry DMF (10 mL) was added, followed by ligand 1 (0.071 mL, 0.45 mmol) and 2-bromopyridine (286 mg, 1.80 mmol). The resulting blue suspension was stirred at it for 5 min, then heated to 100 °C for 16 h. The reaction mixture was then cooled to it, diluted with ethyl acetate (75 mL), then transferred to a separatory funnel and washed with 10% aqueous ammonium chloride. The aqueous phase was extracted with ethyl acetate (3 times 60 mL). The combined organic phases were washed with water (3 times 75 mL) and brine then dried over magnesium sulfate. All the volatiles were evaporated, and the resulting residue was purified by silica gel chromatography with a DCM/MeOH gradient.
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-
-
-
43
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16244411305
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Recent experimental and theoretical studies have indicated that the rate-determining step of the arylation of amides with copper is the oxidative addition. We assumed that a similar reaction mechanism is operative: (a) Strieter, E. R.; Blackmond, D. G.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 4120-4125.
-
(2005)
J. Am. Chem. Soc.
, vol.127
, pp. 4120-4125
-
-
Strieter, E.R.1
Blackmond, D.G.2
Buchwald, S.L.3
-
44
-
-
34548591384
-
-
(b) Zhang, S.-L.; Liu, L.; Fu, Y.; Guo, Q.-X. Qrganometallics 2007, 26, 4546-4554.
-
(2007)
Qrganometallics
, vol.26
, pp. 4546-4554
-
-
Zhang, S.-L.1
Liu, L.2
Fu, Y.3
Guo, Q.-X.4
-
45
-
-
62649152953
-
-
(c) Strieter, E. R.; Bhayana, B.; Buchwald, S. L. J. Am. Chem. Soc. 2009, 131, 16720-16734.
-
(2009)
J. Am. Chem. Soc.
, vol.131
, pp. 16720-16734
-
-
Strieter, E.R.1
Bhayana, B.2
Buchwald, S.L.3
-
47
-
-
0030694323
-
-
Liu, G.; Cogan, D. A.; Ellman, J. A. J. Am. Chem. Soc. 1997, 119, 9913-9914.
-
(1997)
J. Am. Chem. Soc.
, vol.119
, pp. 9913-9914
-
-
Liu, G.1
Cogan, D.A.2
Ellman, J.A.3
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