-
2
-
-
0004101860
-
-
Padwa, A, Ed, Pergamon Press: Oxford
-
(b) Huisgen, R. In 1, 3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Pergamon Press: Oxford, 1984; pp 1-176.
-
(1984)
1, 3-Dipolar Cycloaddition Chemistry
, pp. 1-176
-
-
Huisgen, R.1
-
3
-
-
51049094897
-
-
For leading reviews, see: a
-
For leading reviews, see: (a) Meldal, M.; Tornoe, C. W. Chem. Rev. 2008, 108, 2952.
-
(2008)
Chem. Rev
, vol.108
, pp. 2952
-
-
Meldal, M.1
Tornoe, C.W.2
-
6
-
-
0037696408
-
-
(d) Katritzky, A. R.; Zhang, Y.; Singh, S. K. Heterocycles 2003, 60, 1225.
-
(2003)
Heterocycles
, vol.60
, pp. 1225
-
-
Katritzky, A.R.1
Zhang, Y.2
Singh, S.K.3
-
8
-
-
0000096835
-
-
(f) Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem. Int. Ed. 2001, 40, 2004.
-
(2004)
Angew. Chem. Int. Ed
, vol.2001
, pp. 40
-
-
Kolb, H.C.1
Finn, M.G.2
Sharpless, K.B.3
-
9
-
-
24044531286
-
-
For a review on organic azides, see
-
For a review on organic azides, see: Bräse, S.; Gil, C.; Knepper, K.; Zimmermann, V. Angew. Chem., Int. Ed. 2005, 44, 5188.
-
(2005)
Angew. Chem., Int. Ed
, vol.44
, pp. 5188
-
-
Bräse, S.1
Gil, C.2
Knepper, K.3
Zimmermann, V.4
-
10
-
-
33845249283
-
-
(a) Zhang, X.; Li, H.; You, L.; Tang, Y.; Hsung, R. P. Adv. Syn. Catal. 2006, 348, 2437.
-
(2006)
Adv. Syn. Catal
, vol.348
, pp. 2437
-
-
Zhang, X.1
Li, H.2
You, L.3
Tang, Y.4
Hsung, R.P.5
-
11
-
-
33745830194
-
-
(b) Zhang, X.; Hsung, R. P.; You, L. Org. Biomol. Chem. 2006, 6, 2679.
-
(2006)
Org. Biomol. Chem
, vol.6
, pp. 2679
-
-
Zhang, X.1
Hsung, R.P.2
You, L.3
-
12
-
-
0035801916
-
-
For reviews on ynamides, see: a
-
For reviews on ynamides, see: (a) Zificsak, C. A.; Mulder, J. A.; Hsung, R. P.; Rameshkumar, C.; Wei, L.-L. Tetrahedron 2001, 57, 7575.
-
(2001)
Tetrahedron
, vol.57
, pp. 7575
-
-
Zificsak, C.A.1
Mulder, J.A.2
Hsung, R.P.3
Rameshkumar, C.4
Wei, L.-L.5
-
14
-
-
2942556641
-
-
(c) Katritzky, A. R.; Jiang, R.; Singh, S. K. Heterocycles 2004, 63, 1455.
-
(2004)
Heterocycles
, vol.63
, pp. 1455
-
-
Katritzky, A.R.1
Jiang, R.2
Singh, S.K.3
-
15
-
-
64349091118
-
-
For chemistry of ynamides in the last 2 years, see
-
For chemistry of ynamides in the last 2 years, see:
-
-
-
-
16
-
-
64349100455
-
-
ASAP
-
(a) Couty, S.; Liegault, B.; Meyer, C.; Cossy, J. Tetrahedron 2009, 65, ASAP.
-
(2009)
Tetrahedron
, vol.65
-
-
Couty, S.1
Liegault, B.2
Meyer, C.3
Cossy, J.4
-
17
-
-
59649087158
-
-
(b) Deweerdt, K; Birkedal, H.; Ruhland, T.; Skrydstrup, T. Org. Lett. 2009, 11, 221.
-
(2009)
Org. Lett
, vol.11
, pp. 221
-
-
Deweerdt, K.1
Birkedal, H.2
Ruhland, T.3
Skrydstrup, T.4
-
18
-
-
57449118696
-
-
(c) Dooleweerdt, K; Birkedal, H.; Ruhland, T.; Skrydstrup, T.J. Org. Chem. 2008, 73, 9447.
-
(2008)
J. Org. Chem
, vol.73
, pp. 9447
-
-
Dooleweerdt, K.1
Birkedal, H.2
Ruhland, T.3
Skrydstrup, T.4
-
19
-
-
55949122495
-
-
(d) Saito, N.; Katayama, T.; Sato, Y. Org. Lett. 2008, 10, 3829.
-
(2008)
Org. Lett
, vol.10
, pp. 3829
-
-
Saito, N.1
Katayama, T.2
Sato, Y.3
-
20
-
-
58149307459
-
-
(e) Yasui, H.; Yorimitsu, H.; Oshima, K. Bull. Chem. Soc. Jpn. 2008, 81, 373.
-
(2008)
Bull. Chem. Soc. Jpn
, vol.81
, pp. 373
-
-
Yasui, H.1
Yorimitsu, H.2
Oshima, K.3
-
21
-
-
38949141601
-
-
(f) Yasui, H.; Yorimitsu, H.; Oshima, K. Chem. Lett. 2008, 37, 40.
-
(2008)
Chem. Lett
, vol.37
, pp. 40
-
-
Yasui, H.1
Yorimitsu, H.2
Oshima, K.3
-
22
-
-
51049083425
-
-
(g) Istrate, F. M.; Buzas, A. K; Jurberg, I. D.; Odabachian, Y.; Gagosz, F. Org. Lett 2008, 10, 925.
-
(2008)
Org. Lett
, vol.10
, pp. 925
-
-
Istrate, F.M.1
Buzas, A.K.2
Jurberg, I.D.3
Odabachian, Y.4
Gagosz, F.5
-
23
-
-
40649124041
-
-
(h) Martínez-Esperón, M. F.; Rodríguez, D.; Castedo, L.; Saá, C. Tetrahedron 2008, 64, 3674.
-
(2008)
Tetrahedron
, vol.64
, pp. 3674
-
-
Martínez-Esperón, M.F.1
Rodríguez, D.2
Castedo, L.3
Saá, C.4
-
24
-
-
38349095933
-
-
(i) Hamada, T.; Ye, X.; Stahl, S. S. J. Am. Chem. Soc. 2008, 130, 833.
-
(2008)
J. Am. Chem. Soc
, vol.130
, pp. 833
-
-
Hamada, T.1
Ye, X.2
Stahl, S.S.3
-
25
-
-
37749039142
-
-
(j) Yavari, I.; Sabbaghan, M.; Hosseini, N.; Hossaini, Z. Synlett., 2007, 20, 3172.
-
(2007)
Synlett
, vol.20
, pp. 3172
-
-
Yavari, I.1
Sabbaghan, M.2
Hosseini, N.3
Hossaini, Z.4
-
27
-
-
34547643228
-
-
(l) Rodríguez, D.; Martínez-Esperón, M. F.; Castedo, L.; Saá, C. Synlett., 2007, 1963.
-
(2007)
Synlett
, pp. 1963
-
-
Rodríguez, D.1
Martínez-Esperón, M.F.2
Castedo, L.3
Saá, C.4
-
29
-
-
34548146266
-
-
(n) Movassaghi, M.; Hill, M. D.; Ahmad, O. K. J. Am. Chem. Soc. 2007, 129, 10096.
-
(2007)
J. Am. Chem. Soc
, vol.129
, pp. 10096
-
-
Movassaghi, M.1
Hill, M.D.2
Ahmad, O.K.3
-
31
-
-
85026869890
-
-
(p) Kohnen, A. L.; Dunetz, J. R.; Danheiser, R. L. Org. Synth. 2007, 84, 88.
-
(2007)
Org. Synth
, vol.84
, pp. 88
-
-
Kohnen, A.L.1
Dunetz, J.R.2
Danheiser, R.L.3
-
32
-
-
56449100050
-
-
(a) Al-Rashid, Z. F.; Johnson, W. L.; Hsung, R. P.; Wei, Y.; Yao, P.-Y.; Liu, R.; Zhao, K. J. Org. Chem. 2008, 73, 8780.
-
(2008)
J. Org. Chem
, vol.73
, pp. 8780
-
-
Al-Rashid, Z.F.1
Johnson, W.L.2
Hsung, R.P.3
Wei, Y.4
Yao, P.-Y.5
Liu, R.6
Zhao, K.7
-
33
-
-
55449120798
-
-
(b) Yao, P.-Y.; Zhang, Y.; Hsung, R. P.; Zhao, K. Org. Lett. 2008, 10, 4275.
-
(2008)
Org. Lett
, vol.10
, pp. 4275
-
-
Yao, P.-Y.1
Zhang, Y.2
Hsung, R.P.3
Zhao, K.4
-
34
-
-
54049113119
-
-
(c) Zhang, X.; Hsung, R. P.; Li, H.; Zhang, Y.; Johnson, W. L.; Figueroa, R. Org. Lett 2008, 10, 3477.
-
(2008)
Org. Lett
, vol.10
, pp. 3477
-
-
Zhang, X.1
Hsung, R.P.2
Li, H.3
Zhang, Y.4
Johnson, W.L.5
Figueroa, R.6
-
36
-
-
35048839171
-
-
(e) Oppenheimer, J.; Hsung, R. P.; Figueroa, R.; Johnson, W. L. Org. Lett. 2007, 9, 3969.
-
(2007)
Org. Lett
, vol.9
, pp. 3969
-
-
Oppenheimer, J.1
Hsung, R.P.2
Figueroa, R.3
Johnson, W.L.4
-
37
-
-
34447565958
-
-
(f) You, L.; Al-Rashid, Z. F.; Figueroa, R.; Ghosh, S. K.; Li, G.; Lu, T.; Hsung, R. P. Synlett., 2007, 1656.
-
(2007)
Synlett
, pp. 1656
-
-
You, L.1
Al-Rashid, Z.F.2
Figueroa, R.3
Ghosh, S.K.4
Li, G.5
Lu, T.6
Hsung, R.P.7
-
38
-
-
40749109411
-
-
(g) Li, H.; You, L.; Zhang, X.; Johnson, W. L.; Figueroa, R.; Hsung, R. P. Heterocycles 2007, 74, 553.
-
(2007)
Heterocycles
, vol.74
, pp. 553
-
-
Li, H.1
You, L.2
Zhang, X.3
Johnson, W.L.4
Figueroa, R.5
Hsung, R.P.6
-
39
-
-
85026866955
-
-
(h) Sagamanova, I. K.; Kurtz, K. C. M.; Hsung, R. P. Org. Synth 2007, 84, 359.
-
(2007)
Org. Synth
, vol.84
, pp. 359
-
-
Sagamanova, I.K.1
Kurtz, K.C.M.2
Hsung, R.P.3
-
40
-
-
34250867364
-
-
(i) Oppenheimer, J.; Johnson, W. L.; Tracey, M. R.; Hsung, R. P.; Yao, P.-Y.; Liu, R.; Zhao, K. Org. Leet. 2007, 9, 2361.
-
(2007)
Org. Leet
, vol.9
, pp. 2361
-
-
Oppenheimer, J.1
Johnson, W.L.2
Tracey, M.R.3
Hsung, R.P.4
Yao, P.-Y.5
Liu, R.6
Zhao, K.7
-
41
-
-
4444233074
-
-
Wu, P.; Feldman, A. K.; Nugent, A. K.; Hawker, C. J.; Scheel, A.; Voit, B.; Pyun, J.; Frechet, J. M. J.; Sharpless, K. B.; Fokin, V. V. Angew. Chem., Int. Ed. 2004, 43, 3928.
-
(2004)
Angew. Chem., Int. Ed
, vol.43
, pp. 3928
-
-
Wu, P.1
Feldman, A.K.2
Nugent, A.K.3
Hawker, C.J.4
Scheel, A.5
Voit, B.6
Pyun, J.7
Frechet, J.M.J.8
Sharpless, K.B.9
Fokin, V.V.10
-
43
-
-
33646798112
-
-
For related studies on these triazolyl copper intermediates, see: a
-
For related studies on these triazolyl copper intermediates, see: (a) Gerard, B.; Ryan, J.; Beeler, A. B.; Porco, J. A., Jr. Tetrahedron 2006, 62, 6405.
-
(2006)
Tetrahedron
, vol.62
, pp. 6405
-
-
Gerard, B.1
Ryan, J.2
Beeler, A.B.3
Porco Jr., J.A.4
-
44
-
-
20344373411
-
-
(b) Wu, Y. M.; Deng, J.; Li, Y.; Chen, Q.-Y. Synthesis 2005, 1314.
-
(2005)
Synthesis
, pp. 1314
-
-
Wu, Y.M.1
Deng, J.2
Li, Y.3
Chen, Q.-Y.4
-
45
-
-
33746191914
-
-
See footnote 11
-
(c) Cassidy, M. P.; Raushel, J.; Fokin, V. V. Angew. Chem., Int. Ed. 2006, 45, 3154. See footnote 11..
-
(2006)
Angew. Chem., Int. Ed
, vol.45
, pp. 3154
-
-
Cassidy, M.P.1
Raushel, J.2
Fokin, V.V.3
-
46
-
-
13944272206
-
-
For intermolecular additions, see: a
-
For intermolecular additions, see: (a) Bae, I.; Han, H.; Chang, S. J. Am. Soc. Chem. 2005, 127, 2038.
-
(2005)
J. Am. Soc. Chem
, vol.127
, pp. 2038
-
-
Bae, I.1
Han, H.2
Chang, S.3
-
47
-
-
28044470302
-
-
(b) Cho, S. H.; Yoo, E. J.; Bae, I.; Chang, S. J. Am. Chem. Soc. 2005, 127, 16046.
-
(2005)
J. Am. Chem. Soc
, vol.127
, pp. 16046
-
-
Cho, S.H.1
Yoo, E.J.2
Bae, I.3
Chang, S.4
-
48
-
-
33645942102
-
-
(c) Yoo, E. J.; Bae, I.; Cho, S. H.; Han, H.; Chang, S. Org. Lett. 2006, 8, 1347.
-
(2006)
Org. Lett
, vol.8
, pp. 1347
-
-
Yoo, E.J.1
Bae, I.2
Cho, S.H.3
Han, H.4
Chang, S.5
-
49
-
-
36848999812
-
-
(d) Kim, S. H.; Jung, D. Y.; Chang, S. J. Org. Chem. 2007, 72, 9769.
-
(2007)
J. Org. Chem
, vol.72
, pp. 9769
-
-
Kim, S.H.1
Jung, D.Y.2
Chang, S.3
-
50
-
-
44649165383
-
-
(e) Cho, S. H; Chang, S. Angew. Chem., Int. Ed. 2008, 47, 2836.
-
(2008)
Angew. Chem., Int. Ed
, vol.47
, pp. 2836
-
-
Cho, S.H.1
Chang, S.2
-
51
-
-
57449108893
-
-
(f) Kim, J.; Lee, S. Y.; Lee, J.; Do, Y.; Chang, S. J. Org. Chem. 2008, 73, 9454.
-
(2008)
J. Org. Chem
, vol.73
, pp. 9454
-
-
Kim, J.1
Lee, S.Y.2
Lee, J.3
Do, Y.4
Chang, S.5
-
52
-
-
48249116347
-
-
(g) Yoo, E. J.; Ahlquist, M.; Bae, I.; Sharpless, K. B.; Fokin, V. V.; Chang, S. J. Org. Chem. 2008, 73, 5520.
-
(2008)
J. Org. Chem
, vol.73
, pp. 5520
-
-
Yoo, E.J.1
Ahlquist, M.2
Bae, I.3
Sharpless, K.B.4
Fokin, V.V.5
Chang, S.6
-
53
-
-
33749168701
-
-
For an intramolecular addition, see
-
For an intramolecular addition, see: Chang, S.; Lee, M.; Jung, D. Y.; Yoo, E. J.; Cho, S. H.; Han, S. K. J. Am. Soc. Chem. 2006, 128, 12366.
-
(2006)
J. Am. Soc. Chem
, vol.128
, pp. 12366
-
-
Chang, S.1
Lee, M.2
Jung, D.Y.3
Yoo, E.J.4
Cho, S.H.5
Han, S.K.6
-
54
-
-
38949214728
-
-
For a study using ynamides, see
-
For a study using ynamides, see: Kim, J. Y.; Kim, S. H.; Chang, S. Tetrahedron Lett. 2008, 49, 1745.
-
(2008)
Tetrahedron Lett
, vol.49
, pp. 1745
-
-
Kim, J.Y.1
Kim, S.H.2
Chang, S.3
-
55
-
-
33750071118
-
-
For other leading examples of trapping complexes such as 3, see: (a) Cui, S.-L.; Lin, X.-F.; Wang, Y.-G. Org. Lett 2006, 8, 4517.
-
For other leading examples of trapping complexes such as 3, see: (a) Cui, S.-L.; Lin, X.-F.; Wang, Y.-G. Org. Lett 2006, 8, 4517.
-
-
-
-
56
-
-
34247513022
-
-
(b) Xu, X.; Cheng, D.; Li, J.; Guo, H.; Yan, J. Org. Lett. 2007, 9, 1585.
-
(2007)
Org. Lett
, vol.9
, pp. 1585
-
-
Xu, X.1
Cheng, D.2
Li, J.3
Guo, H.4
Yan, J.5
-
57
-
-
34247146827
-
-
(c) Jin, Y.; Fu, H.; Yin, Y.; Jiang, Y.; Zhao, Y. Synlett 2007, 901.
-
(2007)
Synlett
, pp. 901
-
-
Jin, Y.1
Fu, H.2
Yin, Y.3
Jiang, Y.4
Zhao, Y.5
-
58
-
-
36849057623
-
-
(d) Cui, S.-L.; Wang, J.; Wang, Y.-G. Org. Lett. 2007, 9, 5023.
-
(2007)
Org. Lett
, vol.9
, pp. 5023
-
-
Cui, S.-L.1
Wang, J.2
Wang, Y.-G.3
-
59
-
-
45549084559
-
-
(e) Cui, S.-L.; Wang, J.; Wang, Y.-G. Org. Lett. 2008, 10, 1267.
-
(2008)
Org. Lett
, vol.10
, pp. 1267
-
-
Cui, S.-L.1
Wang, J.2
Wang, Y.-G.3
-
60
-
-
0033597323
-
-
For an earlier study on trapping of ynamido-lithium complexes, see
-
(f) For an earlier study on trapping of ynamido-lithium complexes, see: Fromont, C.; Masson, S. Tetrahedron 1999, 55, 5405.
-
(1999)
Tetrahedron
, vol.55
, pp. 5405
-
-
Fromont, C.1
Masson, S.2
-
62
-
-
64349091990
-
-
For a leading review on amidine derivatives serving as selective muscarinic agonists in the treatment of Alzheimer's diseases, see: Messer, W. S, Jr, Dunbar, P. G. In Muscarinic Agonists and the Treatment of Alzheimer's Disease; Landes Bioscience: Georgetown, TX, 1996; pp 131-153
-
For a leading review on amidine derivatives serving as selective muscarinic agonists in the treatment of Alzheimer's diseases, see: Messer, W. S., Jr.; Dunbar, P. G. In Muscarinic Agonists and the Treatment of Alzheimer's Disease; Landes Bioscience: Georgetown, TX, 1996; pp 131-153.
-
-
-
-
63
-
-
85182954135
-
-
Dunn, P. J. In ComprehensiVe Organic Functional Group Transformations II, Amidines and N-Substituted Amidines; Katritzky, A. R., Taylor, R. J. K., Eds.; Pfizer Global Research and Development: Sandwich, U. K., 2005; 5, pp 655-699.
-
Dunn, P. J. In ComprehensiVe Organic Functional Group Transformations II, Amidines and N-Substituted Amidines; Katritzky, A. R., Taylor, R. J. K., Eds.; Pfizer Global Research and Development: Sandwich, U. K., 2005; Vol. 5, pp 655-699.
-
-
-
-
64
-
-
41449109731
-
-
For recent examples of amidine synthesis, see: a
-
For recent examples of amidine synthesis, see: (a) Yu, R. T.; Rovis, T. J. Am. Chem. Soc. 2008, 130, 3262.
-
(2008)
J. Am. Chem. Soc
, vol.130
, pp. 3262
-
-
Yu, R.T.1
Rovis, T.2
-
65
-
-
38949191566
-
-
(b) Wang, J.; Xu, F.; Cai, T.; Shen, Q. Ore. Lett. 2008, 10, 445.
-
(2008)
Ore. Lett
, vol.10
, pp. 445
-
-
Wang, J.1
Xu, F.2
Cai, T.3
Shen, Q.4
-
66
-
-
64349096884
-
-
(c) Malik, H.; Frederic, B.; Alexandre, M.; Jean-Jacques, B. Org. Biomed. Chem. 2006, 4, 3142.
-
(2006)
Org. Biomed. Chem
, vol.4
, pp. 3142
-
-
Malik, H.1
Frederic, B.2
Alexandre, M.3
Jean-Jacques, B.4
-
67
-
-
33646264574
-
-
(d) Katritzky, A. R.; Cai, C.; Singh, S. K. J. Org. Chem. 2006, 71, 3375.
-
(2006)
J. Org. Chem
, vol.71
, pp. 3375
-
-
Katritzky, A.R.1
Cai, C.2
Singh, S.K.3
-
68
-
-
0842329033
-
-
(e) Kumagai, N.; Matsunaga, S.; Shibasaki, M. Angew. Chem., Int. Ed. 2004, 43, 478.
-
(2004)
Angew. Chem., Int. Ed
, vol.43
, pp. 478
-
-
Kumagai, N.1
Matsunaga, S.2
Shibasaki, M.3
-
69
-
-
64349089534
-
-
See the Supporting Information. On the basis of NOE experiments (see the Supporting Information for details), these amidines adopt an E-geometry with respect to the C=N bond.
-
See the Supporting Information. On the basis of NOE experiments (see the Supporting Information for details), these amidines adopt an E-geometry with respect to the C=N bond.
-
-
-
-
70
-
-
0001029926
-
-
For a leading reference on xantphos, see: Kranenburg, M.; van der Burgt, Y. E. M.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Organomet al.lics 1995, 14, 3081.
-
For a leading reference on xantphos, see: Kranenburg, M.; van der Burgt, Y. E. M.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Organomet al.lics 1995, 14, 3081.
-
-
-
-
71
-
-
0038579438
-
-
For leading references on X-phos, see: a
-
For leading references on X-phos, see: (a) Huang, X.; Anderson, K. W.; Zim, D.; Jiang, L.; Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 6653.
-
(2003)
J. Am. Chem. Soc
, vol.125
, pp. 6653
-
-
Huang, X.1
Anderson, K.W.2
Zim, D.3
Jiang, L.4
Klapars, A.5
Buchwald, S.L.6
-
73
-
-
58149161573
-
-
As shown below, a non-palladium-involved pathway would entail an aza-Claisen type of rearrangement followed by trapping of the allylketenimine intermediate i with an external amine. However, while this pathway is indeed a possibility, it requires much higher temperature and longer reaction time. When carried out at 65-80 °C in THF, the reaction was sluggish and slow. For a recent account on a related thermal transformation using ynol ethers, see: Sosa, J. R.; Tudjarian, A. A.; Minehan, T. G. Org. Lett. 2008, 10, 5091.
-
As shown below, a non-palladium-involved pathway would entail an aza-Claisen type of rearrangement followed by trapping of the allylketenimine intermediate i with an external amine. However, while this pathway is indeed a possibility, it requires much higher temperature and longer reaction time. When carried out at 65-80 °C in THF, the reaction was sluggish and slow. For a recent account on a related thermal transformation using ynol ethers, see: Sosa, J. R.; Tudjarian, A. A.; Minehan, T. G. Org. Lett. 2008, 10, 5091.
-
-
-
-
74
-
-
0003905731
-
-
For leading reviews on Claisen rearrangements, see: a, Morrison, J. D, Ed, Academic Press: New York
-
For leading reviews on Claisen rearrangements, see: (a) Hill, R. K. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984.
-
(1984)
Asymmetric Synthesis
-
-
Hill, R.K.1
-
75
-
-
0000217402
-
-
Trost, B. M, Fleming, I, Eds, Pergamon Press: Oxford
-
(b) Wipf, P. In ComprehensiVe Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, p 827.
-
(1991)
ComprehensiVe Organic Synthesis
, vol.5
, pp. 827
-
-
Wipf, P.1
-
76
-
-
84869275801
-
-
2] from de-allylation were difficult to isolate. However, we were able to isolate the following allylated amine ii when using piperizine.
-
2] from de-allylation were difficult to isolate. However, we were able to isolate the following allylated amine ii when using piperizine.
-
-
-
-
77
-
-
34248573312
-
-
For a leading reference on relative nucleophilicity of amines, see
-
For a leading reference on relative nucleophilicity of amines, see: Brotzel, F.; Chu, Y. C.; Mayr, H. J. Org. Chem. 2007, 72, 3679.
-
(2007)
J. Org. Chem
, vol.72
, pp. 3679
-
-
Brotzel, F.1
Chu, Y.C.2
Mayr, H.3
-
78
-
-
33746092078
-
-
Hartwig observed that in comparison with monodentate phosphine ligands, the usage of bidentate ligands such as xantphos leads to a much faster amidative cross-coupling. This is presumably due to the ability of amido-type carbonyl groups to engage in tight complexation with the palladium met al.. As a result, when using xantphos, its unique bite angle promotes reductive elimination. See: Fujita, K.-I.; Yamashita, M.; Puschmann, F.; Alvarez-Falcon, M. M.; Incarvito, C. D.; Hartwig, J. F. J. Am. Chem. Soc. 2006, 128, 9044.
-
Hartwig observed that in comparison with monodentate phosphine ligands, the usage of bidentate ligands such as xantphos leads to a much faster amidative cross-coupling. This is presumably due to the ability of amido-type carbonyl groups to engage in tight complexation with the palladium met al.. As a result, when using xantphos, its unique bite angle promotes reductive elimination. See: Fujita, K.-I.; Yamashita, M.; Puschmann, F.; Alvarez-Falcon, M. M.; Incarvito, C. D.; Hartwig, J. F. J. Am. Chem. Soc. 2006, 128, 9044.
-
-
-
|