-
1
-
-
33745079610
-
-
J. S. Carey. D. Laffan. C. Thomson, M. T. Williams, Org. Biomol. Chem. 2006, 4, 2337-2347.
-
(2006)
Org. Biomol. Chem.
, vol.4
, pp. 2337-2347
-
-
Carey, J.S.1
Laffan, D.2
Thomson, C.3
Williams, M.T.4
-
7
-
-
57349094283
-
-
For an alternative approach involving direct arylalions of pyridines, which requires high reaction temperatures of usually 130-190°C, see: a
-
For an alternative approach involving direct arylalions of pyridines, which requires high reaction temperatures of usually 130-190°C, see: a) A. M. Berman, J. C. Lewis, R. G. Bergman. J. A. Ellman, J. Am. Chem. Soc. 2008,130, 14926-14927:
-
(2008)
J. Am. Chem. Soc.
, vol.130
, pp. 14926-14927
-
-
Berman, A.M.1
Lewis, J.C.2
Bergman, R.G.3
Ellman, J.A.4
-
8
-
-
69349094999
-
-
Fora representative recent example of direct arylalions with usually oversloichiomelric amounts of pyridine N-oxides as activated pyridine surrogates, see
-
b) M. Tobisu, I. Hyodo, N. Chatani, J. Am. Chem. Soc. 2009, 131, 12070-12071. Fora representative recent example of direct arylalions with usually oversloichiomelric amounts of pyridine N-oxides as activated pyridine surrogates, see:
-
(2009)
J. Am. Chem. Soc.
, vol.131
, pp. 12070-12071
-
-
Tobisu, M.1
Hyodo, I.2
Chatani, N.3
-
9
-
-
67749129343
-
-
and references therein.
-
c) L.-C. Campeau, D. R. Stuart, J.-P. Leclerc, M. Bertrand-Laperle, E. Villemure, H.-Y. Sun, S. Lasserre, N. Guimond, M. Lecavallier, K. Fagnou. J. Am. Chem. Soc. 2009, 131, 3291-3306; and references therein.
-
(2009)
J. Am. Chem. Soc.
, vol.131
, pp. 3291-3306
-
-
Campeau, L.-C.1
Stuart, D.R.2
Leclerc, J.-P.3
Bertrand-Laperle, M.4
Villemure, E.5
Sun, H.-Y.6
Lasserre, S.7
Guimond, N.8
Lecavallier, M.9
Fagnou, K.10
-
11
-
-
67650492323
-
-
Representative examples
-
Representative examples: a) O. Vechorkin, V. Proust, J. Hu, J. Am. Chem. Soc. 2009, 131, 9756-9766;
-
(2009)
J. Am. Chem. Soc.
, vol.131
, pp. 9756-9766
-
-
Vechorkin, O.1
Proust, V.2
Hu, J.3
-
13
-
-
56449107229
-
-
c) N. Yoshikai, H. Malsuda, E. Nakamura, J. Am. Chem. Soc. 2008, 130, 15258-15259;
-
(2008)
J. Am. Chem. Soc.
, vol.130
, pp. 15258-15259
-
-
Yoshikai, N.1
Malsuda, H.2
Nakamura, E.3
-
14
-
-
33644539961
-
-
d) L. Ackermann, R. Born, J. H. Spatz. D. Meyer, Angew. Chem. 2005, 117, 7382-7386;
-
(2005)
Angew. Chem.
, vol.117
, pp. 7382-7386
-
-
Ackermann, L.1
Born, R.2
Spatz, J.H.3
Meyer, D.4
-
15
-
-
27844437252
-
-
Angew. Chem. Int. Ed. 2005, 44, 7216-7219;
-
(2005)
Angew. Chem. Int. Ed.
, vol.44
, pp. 7216-7219
-
-
-
16
-
-
0001432809
-
-
e) V. P. W. Böhm, C. W. K. Gstöltmayr. T. Weskamp, W. A. Herrmann, Angew. Chem. 2001, 113, 3500-3503:
-
(2001)
Angew. Chem.
, vol.113
, pp. 3500-3503
-
-
Böhm, V.P.W.1
Gstöltmayr, C.W.K.2
Weskamp, T.3
Herrmann, W.A.4
-
17
-
-
0035903607
-
-
Angew. Chem. Int. Ed. 2001, 40, 3387-3389;
-
(2001)
Angew. Chem. Int. Ed.
, vol.40
, pp. 3387-3389
-
-
-
18
-
-
0001577807
-
-
f) G. Y. Li, Angew. Chem. 2001, 113, 1561-1564;
-
(2001)
Angew. Chem.
, vol.113
, pp. 1561-1564
-
-
Li, G.Y.1
-
19
-
-
0035901659
-
-
and references therein
-
Angew. Chem. Int. Ed. 2001. 40, 1513-1516; and references therein.
-
(2001)
Angew. Chem. Int. Ed.
, vol.40
, pp. 1513-1516
-
-
-
20
-
-
70349955983
-
-
Recent examples of palladium-catalyzed cross-couplings with Grignard reagents
-
Recent examples of palladium-catalyzed cross-couplings with Grignard reagents, see: a) G. Manolikakes, P. Knöchel. Angew. Chem. 2009, 121, 211-215;
-
(2009)
Angew. Chem.
, vol.121
, pp. 211-215
-
-
Manolikakes, G.1
Knöchel, P.2
-
25
-
-
33845953257
-
-
and references therein
-
e) M. G. Organ, M. Abdel-Hadi, S. Avola. N. Hadei, J. Nasielski, C. J. O'Brien, C. Valente, Chem. Eur. J. 2006, 12, 150-157; and references therein.
-
(2006)
Chem. Eur. J.
, vol.12
, pp. 150-157
-
-
Organ, M.G.1
Abdel-Hadi, M.2
Avola, S.3
Hadei, N.4
Nasielski, J.5
O'Brien, C.J.6
Valente, C.7
-
31
-
-
65249185488
-
-
G. Cahiez, C. Duplais, J. Buendia, Chem. Rev. 2009, 109, 1434-1476.
-
(2009)
Chem. Rev.
, vol.109
, pp. 1434-1476
-
-
Cahiez, G.1
Duplais, C.2
Buendia, J.3
-
33
-
-
33947091124
-
-
K. Tamao, K. Sumitani, M. Kumada, J. Am. Chem. Soc. 1972, 94, 4374-4376.
-
(1972)
J. Am. Chem. Soc.
, vol.94
, pp. 4374-4376
-
-
Tamao, K.1
Sumitani, K.2
Kumada, M.3
-
35
-
-
70149117010
-
-
For select recent examples of Suzuki-Miyaura cross-couplings with 2-pyridyl nucleophiles
-
For select recent examples of Suzuki-Miyaura cross-couplings with 2-pyridyl nucleophiles, see: a) D. M. Knapp, E. P. Gillis, M. D. Burke, J. Am. Chem. Soc. 2009, 131, 6961-6963;
-
(2009)
J. Am. Chem. Soc.
, vol.131
, pp. 6961-6963
-
-
Knapp, D.M.1
Gillis, E.P.2
Burke, M.D.3
-
37
-
-
48849092532
-
-
Angew. Chem. Int. Ed. 2008, 47, 4695-4698;
-
(2008)
Angew. Chem. Int. Ed.
, vol.47
, pp. 4695-4698
-
-
-
39
-
-
84986679674
-
-
for examples of Stille couplings with 2-pyridyltin reagents
-
d) for examples of Stille couplings with 2-pyridyltin reagents, see: Y. Yamamoto, A. Y. Azuma, M. Mitoh, Synthesis 1986, 564-565;
-
(1986)
Synthesis
, pp. 564-565
-
-
Yamamoto, Y.1
Azuma, A.Y.2
Mitoh, M.3
-
40
-
-
0141855415
-
-
and references therein
-
e) R. Wittenberg, J. Srogl, M. Egi, L. S. Liebeskind, Org. Lett. 2003, 5, 3033-3035; and references therein.
-
(2003)
Org. Lett.
, vol.5
, pp. 3033-3035
-
-
Wittenberg, R.1
Srogl, J.2
Egi, M.3
Liebeskind, L.S.4
-
41
-
-
53649097982
-
-
A low-yielding example of a palladium-catalyzed Kumada-Corriu cross-coupling reaction with 2-pyridyl organomagnesium reagents was reported, which highlights the difficulties associated with the use of these nucleophiles
-
A low-yielding example of a palladium-catalyzed Kumada-Corriu cross-coupling reaction with 2-pyridyl organomagnesium reagents was reported, which highlights the difficulties associated with the use of these nucleophiles: a) C. M. Amb, S. C. Rasmussen, Eur. J. Org. Chem. 2008, 801-804;
-
(2008)
Eur. J. Org. Chem.
, pp. 801-804
-
-
Amb, C.M.1
Rasmussen, S.C.2
-
42
-
-
1942460739
-
-
for further unsuccessful attempts
-
b) for further unsuccessful attempts, see, for example: K. Tamao, S. Kodama, I. Nakajima, M. Kumada, A. Minato, K. Suzuki, Tetrahedron 1982, 38, 3347-3354;
-
(1982)
Tetrahedron
, vol.38
, pp. 3347-3354
-
-
Tamao, K.1
Kodama, S.2
Nakajima, I.3
Kumada, M.4
Minato, A.5
Suzuki, K.6
-
43
-
-
30444446752
-
-
see, however, also
-
see, however, also: A. Fürstner, A. Leitner, G. Seidel, Org. Synth. 2005, 81, 33-41.
-
(2005)
Org. Synth.
, vol.81
, pp. 33-41
-
-
Fürstner, A.1
Leitner, A.2
Seidel, G.3
-
45
-
-
33947259131
-
-
Reviews: a
-
Reviews: a) L. Ackermann, Synlett 2007, 507-526;
-
(2007)
Synlett
, pp. 507-526
-
-
Ackermann, L.1
-
47
-
-
33644543729
-
-
L. Ackermann, R. Born, J. H. Spatz, A. Althammer, C. J. Gschrei, Pure Appl Chem. 2006, 78, 209-214.
-
(2006)
Pure Appl Chem.
, vol.78
, pp. 209-214
-
-
Ackermann, L.1
Born, R.2
Spatz, J.H.3
Althammer, A.4
Gschrei, C.J.5
-
49
-
-
33645017030
-
-
b) L. Ackermann, C. J. Gschrei, A. Althammer, M. Riederer, Chem. Commun. 2006, 1419-1421;
-
(2006)
Chem. Commun.
, pp. 1419-1421
-
-
Ackermann, L.1
Gschrei, C.J.2
Althammer, A.3
Riederer, M.4
-
50
-
-
33845219937
-
-
c) L. Ackermann, A. Althammer, R. Born, Angew. Chem. 2006, 118, 2681-2685;
-
(2006)
Angew. Chem.
, vol.118
, pp. 2681-2685
-
-
Ackermann, L.1
Althammer, A.2
Born, R.3
-
51
-
-
33746307336
-
-
Angew. Chem. Int. Ed. 2006, 45, 2619-2622;
-
(2006)
Angew. Chem. Int. Ed.
, vol.45
, pp. 2619-2622
-
-
-
53
-
-
18044384649
-
-
Angew. Chem. Int. Ed. 2005, 44, 2444-2447.
-
(2005)
Angew. Chem. Int. Ed.
, vol.44
, pp. 2444-2447
-
-
-
54
-
-
70350143456
-
-
2P(O)H (7 d) in catalytic functionalizations of C-H bonds, see: a
-
2P(O)H (7 d) in catalytic functionalizations of C-H bonds, see: a) L. Ackermann, R. Vicente, N. Hofmann, Org. Lett. 2009, 11, 4274-4276;
-
(2009)
Org. Lett.
, vol.11
, pp. 4274-4276
-
-
Ackermann, L.1
Vicente, R.2
Hofmann, N.3
-
55
-
-
50249139511
-
-
b) L. Ackermann, R. Vicente, A. Althammer, Org. Lett. 2008, 10, 2299-2302;
-
(2008)
Org. Lett.
, vol.10
, pp. 2299-2302
-
-
Ackermann, L.1
Vicente, R.2
Althammer, A.3
-
57
-
-
77949291765
-
-
The remaining mass balance was unreacted electrophilic starting material
-
The remaining mass balance was unreacted electrophilic starting material.
-
-
-
-
58
-
-
77949303296
-
-
3] did not lead to formation of the desired product.
-
3] did not lead to formation of the desired product.
-
-
-
-
59
-
-
77949304683
-
-
CCDC-713168 contains the supplementary crystallographic data for complex 8. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via data-request/cif
-
CCDC-713168 contains the supplementary crystallographic data for complex 8. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/ data-request/cif.
-
-
-
-
60
-
-
77949309772
-
-
3] (0.5 mol%)/7d (2.0 mol % )/NaOAc (1.0 mol%): 55%
-
3] (0.5 mol%)/7d (2.0 mol % )/NaOAc (1.0 mol%): 55%.
-
-
-
|