-
4
-
-
67650626270
-
-
For selected representatives examples see
-
For selected representatives examples see:
-
-
-
-
6
-
-
27644449720
-
-
Provot O., Giraud A., Payrat J.-F., Alami M., and Brion J.-D. Tetrahedron Lett. 46 (2005) 8547
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(2005)
Tetrahedron Lett.
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Provot, O.1
Giraud, A.2
Payrat, J.-F.3
Alami, M.4
Brion, J.-D.5
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7
-
-
33644779598
-
-
Yamaguchi Y., Ochi T., Wakamiya T., Matsubara Y., and Yoshida Z. Org. Lett. 8 (2006) 717
-
(2006)
Org. Lett.
, vol.8
, pp. 717
-
-
Yamaguchi, Y.1
Ochi, T.2
Wakamiya, T.3
Matsubara, Y.4
Yoshida, Z.5
-
13
-
-
31544457039
-
-
See for an elegant example:
-
See for an elegant example:. Deng X., and Mani N.S. Org. Lett. 8 (2006) 269
-
(2006)
Org. Lett.
, vol.8
, pp. 269
-
-
Deng, X.1
Mani, N.S.2
-
14
-
-
33746494445
-
-
See for a relevant review:
-
See for a relevant review:. Schnürch M., Flasik R., Khan A.F., Spina M., Mihovilovic M.D., and Stanetty P. Eur. J. Org. Chem. (2006) 3283
-
(2006)
Eur. J. Org. Chem.
, pp. 3283
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-
Schnürch, M.1
Flasik, R.2
Khan, A.F.3
Spina, M.4
Mihovilovic, M.D.5
Stanetty, P.6
-
15
-
-
67650619946
-
-
For selected representative examples see
-
For selected representative examples see:
-
-
-
-
22
-
-
3543024496
-
-
Adjabeng G., Brenstrum T., Frampton C.S., Robertson A.J., Hillhouse J., McNulty J., and Capretta A. J. Org. Chem. 69 (2004) 5082
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(2004)
J. Org. Chem.
, vol.69
, pp. 5082
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Adjabeng, G.1
Brenstrum, T.2
Frampton, C.S.3
Robertson, A.J.4
Hillhouse, J.5
McNulty, J.6
Capretta, A.7
-
23
-
-
24344438930
-
-
Hierso J.-C., Fihri A., Amardeil R., Meunier P., Doucet H., and Santelli M. Tetrahedron 61 (2005) 9759
-
(2005)
Tetrahedron
, vol.61
, pp. 9759
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-
Hierso, J.-C.1
Fihri, A.2
Amardeil, R.3
Meunier, P.4
Doucet, H.5
Santelli, M.6
-
24
-
-
6444231126
-
-
Hierso J.-C., Fihri A., Amardeil R., Meunier P., Doucet H., Santelli M., and Ivanov V.V. Org. Lett. 6 (2004) 3473
-
(2004)
Org. Lett.
, vol.6
, pp. 3473
-
-
Hierso, J.-C.1
Fihri, A.2
Amardeil, R.3
Meunier, P.4
Doucet, H.5
Santelli, M.6
Ivanov, V.V.7
-
30
-
-
30944459979
-
-
Brenstrum T., Clattenburg J., Britten J., Zavorine S., Dyck J., Robertson A.J., McNulty J., and Capretta A. Org. Lett. 8 (2006) 103
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(2006)
Org. Lett.
, vol.8
, pp. 103
-
-
Brenstrum, T.1
Clattenburg, J.2
Britten, J.3
Zavorine, S.4
Dyck, J.5
Robertson, A.J.6
McNulty, J.7
Capretta, A.8
-
32
-
-
67650575552
-
-
For selected representatives examples see
-
For selected representatives examples see:
-
-
-
-
34
-
-
0344944884
-
-
Soheili A., Albaneze-Walker J., Murry J.A., Dormer P.G., and Hughes D.L. Org. Lett. 5 (2003) 4191
-
(2003)
Org. Lett.
, vol.5
, pp. 4191
-
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Soheili, A.1
Albaneze-Walker, J.2
Murry, J.A.3
Dormer, P.G.4
Hughes, D.L.5
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39
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0141856212
-
-
Ma Y., Song C., Jiang W., Wu Q., Wang Y., Liu X., and Andrus M.B. Org. Lett. 5 (2003) 3317
-
(2003)
Org. Lett.
, vol.5
, pp. 3317
-
-
Ma, Y.1
Song, C.2
Jiang, W.3
Wu, Q.4
Wang, Y.5
Liu, X.6
Andrus, M.B.7
-
46
-
-
67650575553
-
-
For selected representatives examples see
-
For selected representatives examples see:
-
-
-
-
54
-
-
33947202279
-
-
Li J.-H., Li J.-L., Wang D.-P., Pi S.-F., Xie Y.-X., Zhang M.-B., and Hu X.-C. J. Org. Chem. 72 (2007) 2053
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(2007)
J. Org. Chem.
, vol.72
, pp. 2053
-
-
Li, J.-H.1
Li, J.-L.2
Wang, D.-P.3
Pi, S.-F.4
Xie, Y.-X.5
Zhang, M.-B.6
Hu, X.-C.7
-
55
-
-
34547613945
-
-
Tang B.-X., Wang F., Li J.-H., Xie Y.-X., and Zhang M.-B. J. Org. Chem. 72 (2007) 6294
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(2007)
J. Org. Chem.
, vol.72
, pp. 6294
-
-
Tang, B.-X.1
Wang, F.2
Li, J.-H.3
Xie, Y.-X.4
Zhang, M.-B.5
-
58
-
-
67650606618
-
-
Efficient methodologies tested on a large variety of heteroaromatics are very scarce and employ sophisticated ligands and/or copper co-catalyst, see
-
Efficient methodologies tested on a large variety of heteroaromatics are very scarce and employ sophisticated ligands and/or copper co-catalyst, see:
-
-
-
-
61
-
-
67650575550
-
-
Yang F., Cui X., Li Y.-N., Ren G.-R., and Wu Y. Tetrahedron Lett. 46 (2007) 1717
-
(2007)
Tetrahedron Lett.
, vol.46
, pp. 1717
-
-
Yang, F.1
Cui, X.2
Li, Y.-N.3
Ren, G.-R.4
Wu, Y.5
-
65
-
-
60749123329
-
-
see also Ref. 2b
-
Torborg C., Huang J., Schulz T., Schäffner B., Zapf A., Spannenberg A., Börner A., and Beller M. Chem.-Eur. J. 15 (2009) 1329 see also Ref. 2b
-
(2009)
Chem.-Eur. J.
, vol.15
, pp. 1329
-
-
Torborg, C.1
Huang, J.2
Schulz, T.3
Schäffner, B.4
Zapf, A.5
Spannenberg, A.6
Börner, A.7
Beller, M.8
-
66
-
-
67650623974
-
-
note
-
2 €/mol, from small-scale commercial sources (Sigma-Aldrich 2009 lowest prices).
-
-
-
-
75
-
-
9944232860
-
-
Picquet M., Poinsot D., Stutzmann S., Tkatchenko I., Tommasi I., Wasserscheid P., and Zimmermann J. Top. Catal. 29 (2004) 139
-
(2004)
Top. Catal.
, vol.29
, pp. 139
-
-
Picquet, M.1
Poinsot, D.2
Stutzmann, S.3
Tkatchenko, I.4
Tommasi, I.5
Wasserscheid, P.6
Zimmermann, J.7
-
79
-
-
67650626263
-
-
note
-
4] is among the three cheapest ILs sold by Iolitec from a library of 500 ionic liquids of all current classes.
-
-
-
-
80
-
-
67650593483
-
-
Relevant examples are described
-
Relevant examples are described:
-
-
-
-
81
-
-
0000621561
-
-
Fukuyama T., Shinmen M., Nishitani S., Sato M., and Ryu I. Org. Lett. 4 (2002) 1691
-
(2002)
Org. Lett.
, vol.4
, pp. 1691
-
-
Fukuyama, T.1
Shinmen, M.2
Nishitani, S.3
Sato, M.4
Ryu, I.5
-
86
-
-
42449108650
-
-
Beaupérin M., Fayad E., Amardeil R., Cattey H., Richard P., Brandès S., Meunier P., and Hierso J.-C. Organometallics 27 (2008) 1506
-
(2008)
Organometallics
, vol.27
, pp. 1506
-
-
Beaupérin, M.1
Fayad, E.2
Amardeil, R.3
Cattey, H.4
Richard, P.5
Brandès, S.6
Meunier, P.7
Hierso, J.-C.8
-
87
-
-
67650647058
-
-
note
-
See GC and mass spectrum in Supplementary data.
-
-
-
-
88
-
-
67650584077
-
-
note
-
In Ref. 7e this coupling of 3-bromoquinoline is specially tricky (23% yield of 3-(phenylethynyl)quinoline in 24 h at 130 °C).
-
-
-
-
89
-
-
67650600487
-
-
In Ref. 7f the alkynylation of 3-bromofuran with the activated TMSacetylene from Pd/PPh3 in TMEDA as base and solvent in the presence of CuI is problematic 65% yield in 20 h at 80 °C
-
3 in TMEDA as base and solvent in the presence of CuI is problematic (65% yield in 20 h at 80 °C).
-
-
-
-
90
-
-
67650613832
-
-
Most often 2-halothiophenes couplings are reported, in Ref. 7b is underlined that 3-halothiophenes are more challenging susbtrates since, as electron-excessive heterocycles, thiophenes are more sensitive to halogen position.
-
Most often 2-halothiophenes couplings are reported, in Ref. 7b is underlined that 3-halothiophenes are more challenging susbtrates since, as electron-excessive heterocycles, thiophenes are more sensitive to halogen position.
-
-
-
-
91
-
-
67650581050
-
-
note
-
2.
-
-
-
-
92
-
-
67650630095
-
-
PCT Int. Appl, WO 2005044814, according to this report dihydro-2H-[1,5]benzodioxepin derivatives would be useful as inhibitors of human acetyl-coenzyme A carboxylase ACC, and stimulate fatty acid oxidation in liver and muscle, which might make them suitable as drugs for diabetes, obesity and dyslipidemia
-
Gobbi, L. C.; Gubler, M.; Neidhart, W.; Nettekoven, M. H. PCT Int. Appl., WO 2005044814, 2005, according to this report dihydro-2H-[1,5]benzodioxepin derivatives would be useful as inhibitors of human acetyl-coenzyme A carboxylase (ACC), and stimulate fatty acid oxidation in liver and muscle, which might make them suitable as drugs for diabetes, obesity and dyslipidemia.
-
(2005)
-
-
Gobbi, L.C.1
Gubler, M.2
Neidhart, W.3
Nettekoven, M.H.4
-
94
-
-
67650584076
-
-
4NBr gives only moderate yields of (phenylethynyl)-diheteroaromatics from bromides (43% from 2-Br-thiazole, 46% from 2-Br-pyrimidine, 48% from 2-Br-pyrazine) or from some heteroaromatic chlorides (19% from 2-Cl-pyridine), showing the challenges related to these couplings
-
4NBr gives only moderate yields of (phenylethynyl)-diheteroaromatics from bromides (43% from 2-Br-thiazole, 46% from 2-Br-pyrimidine, 48% from 2-Br-pyrazine) or from some heteroaromatic chlorides (19% from 2-Cl-pyridine), showing the challenges related to these couplings
-
-
-
-
95
-
-
0035914607
-
-
From 2-iodobenzothiazole only a 41% yield was reported for this reaction with Pd/CuI:
-
From 2-iodobenzothiazole only a 41% yield was reported for this reaction with Pd/CuI:. Kumar D., David W.M., and Kerwin S.M. Bioorg. Med. Chem. Lett. 11 (2001) 2971
-
(2001)
Bioorg. Med. Chem. Lett.
, vol.11
, pp. 2971
-
-
Kumar, D.1
David, W.M.2
Kerwin, S.M.3
-
96
-
-
67650585740
-
-
No system was reported, up to now, for this synthesis from aryl chloride in the absence of Cu, and only moderate yield was obtained
-
No system was reported, up to now, for this synthesis from aryl chloride in the absence of Cu, and only moderate yield was obtained:
-
-
-
-
99
-
-
54949124647
-
-
Reinhardt D., Ilgen F., Kralisch D., König B., and Kreisel G. Green Chem. 10 (2008) 1170
-
(2008)
Green Chem.
, vol.10
, pp. 1170
-
-
Reinhardt, D.1
Ilgen, F.2
Kralisch, D.3
König, B.4
Kreisel, G.5
-
100
-
-
0041705653
-
-
Suarez P.A.Z., Einloft S., Dullius J.E.L., de Souza R.F., and Dupont J. Polyhedron 15 (1996) 1271
-
(1996)
Polyhedron
, vol.15
, pp. 1271
-
-
Suarez, P.A.Z.1
Einloft, S.2
Dullius, J.E.L.3
de Souza, R.F.4
Dupont, J.5
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