-
1
-
-
33751281236
-
-
For some recent reviews on the Mizoroki-Heck reaction, see a
-
For some recent reviews on the Mizoroki-Heck reaction, see a)R. F. Heck, Synlett 2006, 2855-2860.
-
(2006)
Synlett
, pp. 2855-2860
-
-
Heck, R.F.1
-
2
-
-
33645865241
-
-
N. T. S. Phan, M. Van Der Sluys, C. W. Jones, Adv. Synth. Catal. 2006, 348, 609-679.
-
(2006)
Adv. Synth. Catal
, vol.348
, pp. 609-679
-
-
Phan, N.T.S.1
Van Der Sluys, M.2
Jones, C.W.3
-
3
-
-
27844611214
-
-
F. Alonso, I. P. Beletskaya, M. Yus, Tetrahedron 2005, 61, 11771-11835.
-
(2005)
Tetrahedron
, vol.61
, pp. 11771-11835
-
-
Alonso, F.1
Beletskaya, I.P.2
Yus, M.3
-
4
-
-
85022586647
-
-
For a few papers on the topic of insertion and regioselectivity, see: a
-
For a few papers on the topic of insertion and regioselectivity, see: a)F. Ozawa, A. Kubo, T. Hayashi, J. Am. Chem. Soc. 1991, 113, 1417-1419.
-
(1991)
J. Am. Chem. Soc
, vol.113
, pp. 1417-1419
-
-
Ozawa, F.1
Kubo, A.2
Hayashi, T.3
-
6
-
-
0000178459
-
-
M. Ludwig, S. Stromberg, M. Svensson, B. Akermark, Organometallics 1999, 18, 970-975.
-
(1999)
Organometallics
, vol.18
, pp. 970-975
-
-
Ludwig, M.1
Stromberg, S.2
Svensson, M.3
Akermark, B.4
-
8
-
-
0001251141
-
-
W. Cabri, I. Candiani, A. Bedeschi, R. Santi, J. Org. Chem. 1992, 57, 3558-3563.
-
(1992)
J. Org. Chem
, vol.57
, pp. 3558-3563
-
-
Cabri, W.1
Candiani, I.2
Bedeschi, A.3
Santi, R.4
-
9
-
-
12944304643
-
-
J. Mo, L. Xu, J. Xiao, J. Am. Chem. Soc. 2005, 127, 751-760.
-
(2005)
J. Am. Chem. Soc
, vol.127
, pp. 751-760
-
-
Mo, J.1
Xu, L.2
Xiao, J.3
-
10
-
-
0034725834
-
-
K. S. A. Vallin, M. Larhed, K. Johansson, A. Hallberg, J. Org. Chem. 2000, 65, 4537-4542.
-
(2000)
J. Org. Chem
, vol.65
, pp. 4537-4542
-
-
Vallin, K.S.A.1
Larhed, M.2
Johansson, K.3
Hallberg, A.4
-
11
-
-
0001113064
-
-
C. Sonesson, M. Larhed, C. Nyquist, A. Hallberg, J. Org. Chem. 1996, 61, 4756-4763.
-
(1996)
J. Org. Chem
, vol.61
, pp. 4756-4763
-
-
Sonesson, C.1
Larhed, M.2
Nyquist, C.3
Hallberg, A.4
-
12
-
-
33749036292
-
-
S. Liu, N. Berry, N. Thomson, A. Pettman, Z. Hyder, J. Mo, J. Xiao, J. Org. Chem. 2006, 71, 7467-7470.
-
(2006)
J. Org. Chem
, vol.71
, pp. 7467-7470
-
-
Liu, S.1
Berry, N.2
Thomson, N.3
Pettman, A.4
Hyder, Z.5
Mo, J.6
Xiao, J.7
-
13
-
-
66349123382
-
-
J. Mo, J. Xiao, Angew. Chem. 2006, 118, 4258-4263; Angew. Chem. Int. Ed. 2006, 45, 4152-4157.
-
J. Mo, J. Xiao, Angew. Chem. 2006, 118, 4258-4263; Angew. Chem. Int. Ed. 2006, 45, 4152-4157.
-
-
-
-
14
-
-
0035874742
-
-
K. S. A. Vallin, M. Larhed, A. Hallberg, J. Org. Chem. 2001, 66, 4340-4343.
-
(2001)
J. Org. Chem
, vol.66
, pp. 4340-4343
-
-
Vallin, K.S.A.1
Larhed, M.2
Hallberg, A.3
-
15
-
-
34547941282
-
-
R. K. Arvela, S. Pasquini, M. Larhed, J. Org. Chem. 2007, 72, 6390-6396.
-
(2007)
J. Org. Chem
, vol.72
, pp. 6390-6396
-
-
Arvela, R.K.1
Pasquini, S.2
Larhed, M.3
-
16
-
-
43949146635
-
-
For some examples, see: a
-
For some examples, see: a) Q. Shen, T. Ogata, J. F. Hartwig, J. Am. Chem. Soc. 2008, 130, 6586-6596.
-
(2008)
J. Am. Chem. Soc
, vol.130
, pp. 6586-6596
-
-
Shen, Q.1
Ogata, T.2
Hartwig, J.F.3
-
19
-
-
24944477864
-
-
and references therein
-
M. D. Charles, P. Schultz, S. L. Buchwald, Org. Lett. 2005, 7, 3965-3968, and references therein.
-
(2005)
Org. Lett
, vol.7
, pp. 3965-3968
-
-
Charles, M.D.1
Schultz, P.2
Buchwald, S.L.3
-
20
-
-
33646464678
-
-
For some examples, see: a
-
For some examples, see: a) A. S. Guram, A. O. King, J. G. Allen, X. Wang, L. B. Schenkel, J. Chan, E. E. Bunel, M. M. Faul, R. D. Larsen, M. J. Martinelli, P. J. Reider, Org. Lett. 2006, 8, 1787-1789.
-
(2006)
Org. Lett
, vol.8
, pp. 1787-1789
-
-
Guram, A.S.1
King, A.O.2
Allen, J.G.3
Wang, X.4
Schenkel, L.B.5
Chan, J.6
Bunel, E.E.7
Faul, M.M.8
Larsen, R.D.9
Martinelli, M.J.10
Reider, P.J.11
-
23
-
-
34447307124
-
-
A. S. Guram, X. Wang, E. E. Bunel, M. M. Faul, R. D. Larsen, M. J. Martinelli, J. Org. Chem. 2007, 72, 5104-5112.
-
(2007)
J. Org. Chem
, vol.72
, pp. 5104-5112
-
-
Guram, A.S.1
Wang, X.2
Bunel, E.E.3
Faul, M.M.4
Larsen, R.D.5
Martinelli, M.J.6
-
24
-
-
1242322462
-
-
For some examples, see: a
-
For some examples, see: a) B. H. Kaae, P. Krogsgaard-Larsen, T. N. Johansen, J. Org. Chem. 2004, 69, 1401-1404.
-
(2004)
J. Org. Chem
, vol.69
, pp. 1401-1404
-
-
Kaae, B.H.1
Krogsgaard-Larsen, P.2
Johansen, T.N.3
-
25
-
-
52449111842
-
-
S. Sase, M. Jaric, A. Metzger, V. Malakhov, P. Knochel, J. Org. Chem. 2008, 73, 7380-7382.
-
(2008)
J. Org. Chem
, vol.73
, pp. 7380-7382
-
-
Sase, S.1
Jaric, M.2
Metzger, A.3
Malakhov, V.4
Knochel, P.5
-
26
-
-
55249105544
-
-
G. Manolikakes, M. A. Schade, C. M. Hernandez, H. Mayr, P. Knochel, Org. Lett. 2008, 10, 2765-2768.
-
(2008)
Org. Lett
, vol.10
, pp. 2765-2768
-
-
Manolikakes, G.1
Schade, M.A.2
Hernandez, C.M.3
Mayr, H.4
Knochel, P.5
-
27
-
-
33749121805
-
-
For some examples, see: a
-
For some examples, see: a) R. J. Brea, M. P. Lopez-Deber, L. Castedo, J. R. Granja, J. Org. Chem. 2006, 71, 7870-7873.
-
(2006)
J. Org. Chem
, vol.71
, pp. 7870-7873
-
-
Brea, R.J.1
Lopez-Deber, M.P.2
Castedo, L.3
Granja, J.R.4
-
28
-
-
0037458874
-
-
A. S. Karpov, F. Rominger, T. J. J. Müller, J. Org. Chem. 2003, 68, 1503-1511.
-
(2003)
J. Org. Chem
, vol.68
, pp. 1503-1511
-
-
Karpov, A.S.1
Rominger, F.2
Müller, T.J.J.3
-
29
-
-
26444432281
-
-
For references on heteroaromatic MH-coupling reactions with halide electrophiles: Ref. [5c, 6b]; aT. J. Kwok, J. A. Virgilio, Org. Process Res. Dev. 2005, 9, 694-696.
-
For references on heteroaromatic MH-coupling reactions with halide electrophiles: Ref. [5c, 6b]; a)T. J. Kwok, J. A. Virgilio, Org. Process Res. Dev. 2005, 9, 694-696.
-
-
-
-
30
-
-
52049103654
-
-
J.-X. Wang, J. A. McCubbin, M. Jin, R. S. Laufer, Y. Mao, A. P. Crew, M. J. Mulvihill, V. Snieckus, Org. Lett. 2008, 10, 2923-2926.
-
(2008)
Org. Lett
, vol.10
, pp. 2923-2926
-
-
Wang, J.-X.1
McCubbin, J.A.2
Jin, M.3
Laufer, R.S.4
Mao, Y.5
Crew, A.P.6
Mulvihill, M.J.7
Snieckus, V.8
-
31
-
-
41349116314
-
-
T. He, T. Xiaochun, X. Wu, X. Cai, V. W. Pike, Synthesis 2008, 887-890.
-
(2008)
Synthesis
, pp. 887-890
-
-
He, T.1
Xiaochun, T.2
Wu, X.3
Cai, X.4
Pike, V.W.5
-
33
-
-
0344535125
-
-
T. Sakamoto, Y. Kondo, Y.Kashiwagi, H. Yamanaka, Heterocycles 1988, 27, 257-260.
-
(1988)
Heterocycles
, vol.27
, pp. 257-260
-
-
Sakamoto, T.1
Kondo, Y.2
Kashiwagi, Y.3
Yamanaka, H.4
-
34
-
-
40949101252
-
-
For references on heteroaromatic MH-coupling reactions with triflate electrophiles
-
Z. Liu, D. Xu, W. Tang, L. Xu, J. Mo, J. Xiao, Tetrahedron Lett. 2008, 49, 2756-2760. For references on heteroaromatic MH-coupling reactions with triflate electrophiles.
-
(2008)
Tetrahedron Lett
, vol.49
, pp. 2756-2760
-
-
Liu, Z.1
Xu, D.2
Tang, W.3
Xu, L.4
Mo, J.5
Xiao, J.6
-
35
-
-
0036325514
-
-
C. Shin, A. Okabe, A. Ito, A. Ito, Y. Yonezawa, Bull. Chem. Soc. Jpn. 2002, 75, 1583-1596.
-
(2002)
Bull. Chem. Soc. Jpn
, vol.75
, pp. 1583-1596
-
-
Shin, C.1
Okabe, A.2
Ito, A.3
Ito, A.4
Yonezawa, Y.5
-
36
-
-
0030052780
-
-
C. Subramanyam, S. Chattarjee, J. P. Mallamo, Tetrahedron Lett. 1996, 37, 459-462.
-
(1996)
Tetrahedron Lett
, vol.37
, pp. 459-462
-
-
Subramanyam, C.1
Chattarjee, S.2
Mallamo, J.P.3
-
37
-
-
0031871141
-
-
K. Okumura, H. Saito, C. Shin, K. Umemura, J. Yoshimura, Bull. Chem. Soc. Jpn. 1998, 71, 1863-1870.
-
(1998)
Bull. Chem. Soc. Jpn
, vol.71
, pp. 1863-1870
-
-
Okumura, K.1
Saito, H.2
Shin, C.3
Umemura, K.4
Yoshimura, J.5
-
38
-
-
0030922051
-
-
K. Umemura, H. Noda, J. Yoshimura, A. Konn, Y. Yonezawa, C. Shin, Tetrahedron Lett. 1997, 38, 3539-3542.
-
(1997)
Tetrahedron Lett
, vol.38
, pp. 3539-3542
-
-
Umemura, K.1
Noda, H.2
Yoshimura, J.3
Konn, A.4
Yonezawa, Y.5
Shin, C.6
-
39
-
-
0032560146
-
-
W. Ajana, L. Feliu, M. Alvarez, J. A. Joule, Tetrahedron 1998, 54, 4405-4412.
-
(1998)
Tetrahedron
, vol.54
, pp. 4405-4412
-
-
Ajana, W.1
Feliu, L.2
Alvarez, M.3
Joule, J.A.4
-
41
-
-
66349095842
-
-
N-Vinyl acetamide is commercially available.
-
N-Vinyl acetamide is commercially available.
-
-
-
-
42
-
-
33749562133
-
-
Djakovitch and co-workers reported a 30% conversion in the MH coupling of 8-quinolinyl mesylate to acrolein. To our knowledge this is the only reported example of a non-fluorinated sulfonate as an electrophile in an MH coupling, see: S. Noël, C. Pinel, L. Djakovitch, Org. Biomol. Chem. 2006, 4, 3760-3762.
-
Djakovitch and co-workers reported a 30% conversion in the MH coupling of 8-quinolinyl mesylate to acrolein. To our knowledge this is the only reported example of a non-fluorinated sulfonate as an electrophile in an MH coupling, see: S. Noël, C. Pinel, L. Djakovitch, Org. Biomol. Chem. 2006, 4, 3760-3762.
-
-
-
-
43
-
-
60849137210
-
-
In solution, the 2-hydroxy pyridines are in equilibrium with their tautomeric pyridinone species. In some cases, this resulted in mixtures of isomeric tosylates which however were separable by column chromatography, see: F.-A. Kang, Z. Sui, W. V. Murray, Eur. J. Org. Chem. 2009, 461-479, and references therein.
-
In solution, the 2-hydroxy pyridines are in equilibrium with their tautomeric pyridinone species. In some cases, this resulted in mixtures of isomeric tosylates which however were separable by column chromatography, see: F.-A. Kang, Z. Sui, W. V. Murray, Eur. J. Org. Chem. 2009, 461-479, and references therein.
-
-
-
-
46
-
-
3543019095
-
-
For recent Mizoroki-Heck-coupling reactions with enamides see: Ref. [10f]; aM. M. S. Andappan, P. Nilsson, H. von Schenck, M. Larhed, J. Org. Chem. 2004, 69, 5212-5218.
-
For recent Mizoroki-Heck-coupling reactions with enamides see: Ref. [10f]; a)M. M. S. Andappan, P. Nilsson, H. von Schenck, M. Larhed, J. Org. Chem. 2004, 69, 5212-5218.
-
-
-
-
47
-
-
0042510061
-
-
K. S. A. Vallin, Q.Zhang, M. Larhed, D. P. Curran, A. Hallberg, J. Org. Chem. 2003, 68, 6639-6645.
-
(2003)
J. Org. Chem
, vol.68
, pp. 6639-6645
-
-
Vallin, K.S.A.1
Zhang, Q.2
Larhed, M.3
Curran, D.P.4
Hallberg, A.5
-
49
-
-
66349095254
-
-
No reaction was observed with the similar O,O-diphenyl-or O,O-diethyl 2-pyridyl phosphates with full recovery of the starting materials.
-
No reaction was observed with the similar O,O-diphenyl-or O,O-diethyl 2-pyridyl phosphates with full recovery of the starting materials.
-
-
-
-
51
-
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66349126046
-
-
See the Supporting Information for precise experimental details in the scale-up study
-
See the Supporting Information for precise experimental details in the scale-up study.
-
-
-
-
52
-
-
60949083370
-
-
For some recent examples on asymmetric reduction of N-acyl α-arylvinyl amines, see: aC.-J. Wang, F. Gao, G. Liang, Org. Lett. 2008, 10, 4711-4714.
-
For some recent examples on asymmetric reduction of N-acyl α-arylvinyl amines, see: a)C.-J. Wang, F. Gao, G. Liang, Org. Lett. 2008, 10, 4711-4714.
-
-
-
-
53
-
-
66349128645
-
-
W. Zhang, X. Zhang, Angew. Chem. 2006, 118, 5641-5644; Angew. Chem. Int. Ed. 2006, 45, 5515-5518.
-
W. Zhang, X. Zhang, Angew. Chem. 2006, 118, 5641-5644; Angew. Chem. Int. Ed. 2006, 45, 5515-5518.
-
-
-
-
54
-
-
1842557260
-
-
and references therein
-
H. Huang, Z. Zheng, H. Luo, C. Bai, C. Hu, H. Chen, J. Org. Chem. 2004, 69, 2355-2361, and references therein.
-
(2004)
J. Org. Chem
, vol.69
, pp. 2355-2361
-
-
Huang, H.1
Zheng, Z.2
Luo, H.3
Bai, C.4
Hu, C.5
Chen, H.6
-
55
-
-
66349132896
-
-
D. Gelman, S. L. Buchwald, Angew. Chem. 2003, 115, 6175-6178; Angew. Chem. Int. Ed. 2003, 42, 5993-5996.
-
D. Gelman, S. L. Buchwald, Angew. Chem. 2003, 115, 6175-6178; Angew. Chem. Int. Ed. 2003, 42, 5993-5996.
-
-
-
-
57
-
-
0034600318
-
-
A. F. Littke, C. Dai, G. C. Fu, J. Am. Chem. Soc. 2000, 122, 4020-4028.
-
(2000)
J. Am. Chem. Soc
, vol.122
, pp. 4020-4028
-
-
Littke, A.F.1
Dai, C.2
Fu, G.C.3
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