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Miyaura, N.1
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0001480580
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Both base- and metal-catalyzed deboronation of boronic acids may occur under typical SMC reactions
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Both base- and metal-catalyzed deboronation of boronic acids may occur under typical SMC reactions. Kuivila, H. G., Reuwer, J. F., and Mangravite, J. A. Can. J. Chem. 1963, 41, 3081
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6
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77957700097
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While 2,3- and 2,4-difluorophenylboronic acids could be coupled using ligand SPhos at 80-90 °C, these conditions did not allow the efficient coupling of 1 or 2
-
While 2,3- and 2,4-difluorophenylboronic acids could be coupled using ligand SPhos at 80-90 °C, these conditions did not allow the efficient coupling of 1 or 2
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7
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16844367937
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Barder, T. E., Walker, S. D., Martinelli, J. R., and Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 4685
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8
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77957703524
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For some examples for the coupling of 2,6-difluorophenylboronic acid with vinyl triflates and aryl bromides, see
-
For some examples for the coupling of 2,6-difluorophenylboronic acid with vinyl triflates and aryl bromides, see
-
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11
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15044361867
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Palmer, B. D., Smaill, J. B., Rewcastle, G. W., Dobrusin, E. M., Kraker, A., Moore, C. W., Steinkampf, R. W., and Denny, W. A. Bioorg. Med. Chem. Lett. 2005, 15, 1931
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Palmer, B.D.1
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Kraker, A.5
Moore, C.W.6
Steinkampf, R.W.7
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12
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Billingsley, K. L., Anderson, K. W., and Buchwald, S. L. Angew. Chem., Int. Ed. 2006, 45, 3484
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Billingsley, K.L.1
Anderson, K.W.2
Buchwald, S.L.3
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16
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77957702874
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For some representative examples of the coupling of five-membered 2-heteroaromatic boronic acids, see
-
For some representative examples of the coupling of five-membered 2-heteroaromatic boronic acids, see
-
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17
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68349088939
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Kabri, Y., Gellis, A., and Vanelle, P. Eur. J. Org. Chem. 2009, 24, 4059
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Kabri, Y.1
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38849184650
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Gill, G. S., Grobelny, D. W., Chaplin, J. H., and Flynn, B. L. J. Org. Chem. 2008, 73, 1131
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Gill, G.S.1
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70349782152
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Organ, M., Çalimsiz, S., Sayah, M., Hoi, K., and Lough, A. Angew. Chem., Int. Ed. 2009, 48, 2383
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Organ, M.1
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Maeda, H., Haketa, Y., and Nakanishi, T. J. Am. Chem. Soc. 2007, 129, 13661
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Maeda, H.1
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James, C. A., Coelho, A. L., Gevaert, M., Forgione, P., and Snieckus, V. J. Org. Chem. 2009, 74, 4094
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James, C.A.1
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23
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77957695778
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2-heterocyclic MIDA boronates were successfully employed for SMCs (see ref 4a), but polyfluorophenyl MIDA boronates were not described. MIDA = N -methyliminodiacetic acid
-
2-heterocyclic MIDA boronates were successfully employed for SMCs (see ref 4a), but polyfluorophenyl MIDA boronates were not described. MIDA = N -methyliminodiacetic acid.
-
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24
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38549118405
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Yamamoto, Y., Takizawa, M., Yu, X., and Miyaura, N. Angew. Chem., Int. Ed. 2008, 47, 928
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Yamamoto, Y.1
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25
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77957700620
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3K salts were coupled to 4-bromobenzonitrile
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3K salts were coupled to 4-bromobenzonitrile
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27
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77957719316
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3K salts
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3K salts
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28
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64549100485
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Molander, G.A.1
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Kennedy, L.E.3
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29
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77957690997
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3K salts to the free boronic acid likely occurs prior to cross-coupling
-
3K salts to the free boronic acid likely occurs prior to cross-coupling
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30
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77954846356
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Butters, M., Harvey, J. N., Jover, J., Lennox, A. J. J., Lloyd-Jones, G. C., and Murray, P. Angew. Chem., Int. Ed. 2010, 49, 5156
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33
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43449085777
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Adonin, N. Y., Babushkin, D. E., Parmon, V. N., Bardin, V. V., Kostin, G. A., Mashukov, V. I., and Frohn, H. Tetrahedron 2008, 64, 5920
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Adonin, N.Y.1
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Mashukov, V.I.6
Frohn, H.7
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34
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77957690828
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It should be mentioned that with copper or palladium catalysts, aryl bromides and chlorides can be directly coupled to polyfluorobenzenes via C-H activation processes, but high temperatures and long reaction times are required
-
It should be mentioned that with copper or palladium catalysts, aryl bromides and chlorides can be directly coupled to polyfluorobenzenes via C-H activation processes, but high temperatures and long reaction times are required.
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35
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33750920283
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Lafrance, M., Shore, D., and Fagnou, K. Org. Lett. 2006, 8, 5097
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Barder, T. E., Biscoe, M. R., and Buchwald, S. L. Organometallics 2007, 26, 2183
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38
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77957701173
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The reductive elimination of 4-methoxy-2′,6′-difluorobiphenyl from an isolated Pd(II) complex has been reported
-
The reductive elimination of 4-methoxy-2′,6′-difluorobiphenyl from an isolated Pd(II) complex has been reported
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39
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12844288658
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Osakada, K., Onodera, H., and Nishihara, Y. Organometallics 2005, 24, 190
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Albert, J.1
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42
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77957691172
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-.
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43
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77957708140
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2O/pyridine mixture at elevated temperatures were reported
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2O/pyridine mixture at elevated temperatures were reported
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-
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44
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0036943387
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Frohn, H., Adonin, N. Y., Bardin, V. V., and Starichenko, V. F. Z. Anorg. Allg. Chem. 2002, 628, 2834
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Frohn, H.1
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Starichenko, V.F.4
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45
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77957699042
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4 solution prior to addition of the precatalyst and aryl chloride, and we found the same ratio of products as before
-
4 solution prior to addition of the precatalyst and aryl chloride, and we found the same ratio of products as before.
-
-
-
-
46
-
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77957717643
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The attempted coupling of 2,3,6-trifluorophenylboronic acid with 4-chloroacetophenone under microwave irradiation led exclusively to the deboronated compound, trifluorobenzene
-
The attempted coupling of 2,3,6-trifluorophenylboronic acid with 4-chloroacetophenone under microwave irradiation led exclusively to the deboronated compound, trifluorobenzene
-
-
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47
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34347340382
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Clarke, M. L., France, M. B., Fuentes, J. A., Milton, E. J., and Roff, J. R. Beilstein J. Chem. 2007, 3, 18
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Clarke, M.L.1
France, M.B.2
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Milton, E.J.4
Roff, J.R.5
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