-
1
-
-
33645674829
-
-
For recent reviews, see: a
-
For recent reviews, see: a) K. Godula, D. Sames, Science 2006, 312, 67;
-
(2006)
Science
, vol.312
, pp. 67
-
-
Godula, K.1
Sames, D.2
-
5
-
-
0042881024
-
-
For recent reviews, see: a
-
For recent reviews, see: a) P. Müller, C. Fruit, Chem. Rev. 2003, 103, 2905;
-
(2003)
Chem. Rev
, vol.103
, pp. 2905
-
-
Müller, P.1
Fruit, C.2
-
11
-
-
0003394220
-
-
Wiley, New York
-
M. P. Doyle, M. A. McKervey, T. Ye, Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: From Cyclopropanes to Ylides, Wiley, New York, 1998.
-
(1998)
Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: From Cyclopropanes to Ylides
-
-
Doyle, M.P.1
McKervey, M.A.2
Ye, T.3
-
13
-
-
37049095037
-
-
b) D. Mansuy, J.-P. Mahy, A. Duréault, G. Bedi, P. Battioni, J. Chem. Soc. Chem. Commun. 1984, 1161.
-
(1984)
J. Chem. Soc. Chem. Commun
, pp. 1161
-
-
Mansuy, D.1
Mahy, J.-P.2
Duréault, A.3
Bedi, G.4
Battioni, P.5
-
14
-
-
53549090327
-
-
Generated in situ: a C. G. Espino, J. Du Bois, Angew. Chem. 2001, 113, 618;
-
Generated in situ: a) C. G. Espino, J. Du Bois, Angew. Chem. 2001, 113, 618;
-
-
-
-
16
-
-
0034794306
-
-
b) P. Dauban, L. Sanière, A. Tarrade, R. H. Dodd, J. Am. Chem. Soc. 2001, 123, 7707.
-
(2001)
J. Am. Chem. Soc
, vol.123
, pp. 7707
-
-
Dauban, P.1
Sanière, L.2
Tarrade, A.3
Dodd, R.H.4
-
17
-
-
33744786786
-
-
Recent reports: a X. Chen, X.-S. Hao, C. E. Goodhue, J.-Q. Yu, J. Am. Chem. Soc. 2006, 128, 6790;
-
Recent reports: a) X. Chen, X.-S. Hao, C. E. Goodhue, J.-Q. Yu, J. Am. Chem. Soc. 2006, 128, 6790;
-
-
-
-
18
-
-
33746071928
-
-
b) H.-Y. Thu, W.-Y. Yu, C.-M. Che, J. Am. Chem. Soc. 2006, 128, 9048;
-
(2006)
J. Am. Chem. Soc
, vol.128
, pp. 9048
-
-
Thu, H.-Y.1
Yu, W.-Y.2
Che, C.-M.3
-
19
-
-
33947689674
-
-
c) A. R. Dick, M. S. Remy, J. W. Kampf, M. S. Sanford, Organometallics 2007, 26, 1365;
-
(2007)
Organometallics
, vol.26
, pp. 1365
-
-
Dick, A.R.1
Remy, M.S.2
Kampf, J.W.3
Sanford, M.S.4
-
20
-
-
35048903503
-
-
d) Z. Li, D. A. Capretto, R. O. Rahaman, C. He, J. Am. Chem. Soc. 2007, 129, 12058.
-
(2007)
J. Am. Chem. Soc
, vol.129
, pp. 12058
-
-
Li, Z.1
Capretto, D.A.2
Rahaman, R.O.3
He, C.4
-
23
-
-
0000574395
-
-
c) H. Hemetsberger, D. Knittel, H. Weidmann, Monatsh. Chem. 1970, 101, 161;
-
(1970)
Monatsh. Chem
, vol.101
, pp. 161
-
-
Hemetsberger, H.1
Knittel, D.2
Weidmann, H.3
-
24
-
-
0001600375
-
-
d) R. J. Sundberg, H. F. Russell, W. V. Ligon, Jr., L.-S. Lin, J. Org. Chem. 1972, 37, 719.
-
(1972)
J. Org. Chem
, vol.37
, pp. 719
-
-
Sundberg, R.J.1
Russell, H.F.2
Ligon Jr., W.V.3
Lin, L.-S.4
-
25
-
-
31944441649
-
-
Azirines can also function as nitrene precursors. For recent work, see
-
Azirines can also function as nitrene precursors. For recent work, see: D. F. Taber, W. Tian, J. Am. Chem. Soc. 2006, 128, 1058.
-
(2006)
J. Am. Chem. Soc
, vol.128
, pp. 1058
-
-
Taber, D.F.1
Tian, W.2
-
27
-
-
0008384277
-
-
Eds, B. M. Trost, I. Fleming, S. Ley, Pergamon, Oxford
-
b) C. J. Moody, Comprehensive Organic Synthesis, Vol. 7, (Eds.: B. M. Trost, I. Fleming, S. Ley), Pergamon, Oxford, 1991, p. 21;
-
(1991)
Comprehensive Organic Synthesis
, vol.7
, pp. 21
-
-
Moody, C.J.1
-
29
-
-
29344457003
-
-
Reviews: a
-
Reviews: a) T. Katsuki, Chem. Lett. 2005, 34, 1304;
-
(2005)
Chem. Lett
, vol.34
, pp. 1304
-
-
Katsuki, T.1
-
30
-
-
33747052051
-
-
b) S. Cenini, E. Gallo, A. Caselli, F. Ragaini, S. Fantauzzi, C. Piangiolino, Coord. Chem. Rev. 2006, 250, 1234.
-
(2006)
Coord. Chem. Rev
, vol.250
, pp. 1234
-
-
Cenini, S.1
Gallo, E.2
Caselli, A.3
Ragaini, F.4
Fantauzzi, S.5
Piangiolino, C.6
-
31
-
-
33747469456
-
-
For recent reports, see: a
-
For recent reports, see: a) G.-Y. Gao, J. E. Jones, R. Vyas, J. D. Harden, X. P. Zhang, J. Org. Chem. 2006, 71, 6655;
-
(2006)
J. Org. Chem
, vol.71
, pp. 6655
-
-
Gao, G.-Y.1
Jones, J.E.2
Vyas, R.3
Harden, J.D.4
Zhang, X.P.5
-
32
-
-
34250622480
-
-
b) C. Piangiolino, E. Gallo, A. Caselli, S. Fantauzzi, F. Ragaini, S. Cenini, Eur. J. Org. Chem. 2007, 743;
-
(2007)
Eur. J. Org. Chem
, pp. 743
-
-
Piangiolino, C.1
Gallo, E.2
Caselli, A.3
Fantauzzi, S.4
Ragaini, F.5
Cenini, S.6
-
33
-
-
36348935688
-
-
c) J. V. Ruppel, R. M. Kamble, X. P. Zhang, Org. Lett. 2007, 9, 4889.
-
(2007)
Org. Lett
, vol.9
, pp. 4889
-
-
Ruppel, J.V.1
Kamble, R.M.2
Zhang, X.P.3
-
34
-
-
0001286831
-
-
3 was decomposed photochemically in the presence of styrene and a rhodium(II) bis(naphthol)phosphate catalyst to produce an aziridine in 9% yield, see: P. Mueller, C. Baud, I. Naegeli, J. Phys. Org. Chem. 1998, 11, 597.
-
3 was decomposed photochemically in the presence of styrene and a rhodium(II) bis(naphthol)phosphate catalyst to produce an aziridine in 9% yield, see: P. Mueller, C. Baud, I. Naegeli, J. Phys. Org. Chem. 1998, 11, 597.
-
-
-
-
35
-
-
13444287715
-
-
4] to accelerate the transformation of a single vinyl azide to indole at 115°C, see: J. Sawyer, D. W. Beight, E. C. R. Smith, D. W. Snyder, M. K. Chastain, R. L. Tielking, L. W. Hartley, D. G. Carlson, J. Med. Chem. 2005, 48, 893.
-
4] to accelerate the transformation of a single vinyl azide to indole at 115°C, see: J. Sawyer, D. W. Beight, E. C. R. Smith, D. W. Snyder, M. K. Chastain, R. L. Tielking, L. W. Hartley, D. G. Carlson, J. Med. Chem. 2005, 48, 893.
-
-
-
-
36
-
-
34247262117
-
-
4-catalyzed isomerization of aryl azirines, see: S. Chiba, G. Hattori, K. Narasaka, Chem. Lett. 2007, 36, 52.
-
4-catalyzed isomerization of aryl azirines, see: S. Chiba, G. Hattori, K. Narasaka, Chem. Lett. 2007, 36, 52.
-
-
-
-
37
-
-
0001498958
-
-
For reviews of azide reactivity, see: a
-
For reviews of azide reactivity, see: a) G. L'abbé, Angew. Chem. 1975, 87, 831;
-
(1975)
Angew. Chem
, vol.87
, pp. 831
-
-
L'abbé, G.1
-
39
-
-
27944494395
-
-
b) S. Bräse, C. Gil, K. Knepper, V. Zimmermann, Angew. Chem. 2005, 117, 5320;
-
(2005)
Angew. Chem
, vol.117
, pp. 5320
-
-
Bräse, S.1
Gil, C.2
Knepper, K.3
Zimmermann, V.4
-
41
-
-
85007922556
-
-
Aryl and vinyl azides are easily synthesized. See: a) reference [8b];
-
reference
-
-
-
42
-
-
53549088494
-
-
reference [10a];
-
b) reference [10a];
-
-
-
-
43
-
-
37049095153
-
-
c) L. Henn, D. M. B. Hickey, C. J. Moody, C. W. Rees, J. Chem. Soc. Perkin Trans. 1 1984, 2189;
-
(1984)
J. Chem. Soc. Perkin Trans. 1
, pp. 2189
-
-
Henn, L.1
Hickey, D.M.B.2
Moody, C.J.3
Rees, C.W.4
-
44
-
-
0000540188
-
-
d) F. W. Fowler, A. Hassner, L. A. Levy, J. Am. Chem. Soc. 1967, 89, 2077;
-
(1967)
J. Am. Chem. Soc
, vol.89
, pp. 2077
-
-
Fowler, F.W.1
Hassner, A.2
Levy, L.A.3
-
48
-
-
34250851338
-
-
a) B. J. Stokes, H. Dong, B. E. Leslie, A. L. Pumphrey, T. G. Driver, J. Am. Chem. Soc. 2007, 129, 7500;
-
(2007)
J. Am. Chem. Soc
, vol.129
, pp. 7500
-
-
Stokes, B.J.1
Dong, H.2
Leslie, B.E.3
Pumphrey, A.L.4
Driver, T.G.5
-
49
-
-
37249000768
-
-
b) H. Dong, M. Shen, J. E. Redford, B. J. Stokes, A. L. Pumphrey, T. G. Driver, Org. Lett. 2007, 9, 5191.
-
(2007)
Org. Lett
, vol.9
, pp. 5191
-
-
Dong, H.1
Shen, M.2
Redford, J.E.3
Stokes, B.J.4
Pumphrey, A.L.5
Driver, T.G.6
-
50
-
-
6444224511
-
-
For recent examples of anilines employed as substrates in the Suzuki reaction, see: a
-
For recent examples of anilines employed as substrates in the Suzuki reaction, see: a) Y. Wu, J. Li, Y. Fu, Z. Bo, Org. Lett. 2004, 6, 3485;
-
(2004)
Org. Lett
, vol.6
, pp. 3485
-
-
Wu, Y.1
Li, J.2
Fu, Y.3
Bo, Z.4
-
51
-
-
33745473200
-
-
b) Y. Miura, Y. Muranaka, Y. Teki, J. Org. Chem. 2006, 71, 4786.
-
(2006)
J. Org. Chem
, vol.71
, pp. 4786
-
-
Miura, Y.1
Muranaka, Y.2
Teki, Y.3
-
52
-
-
53549103208
-
-
Please refer to the Supporting Information for more details
-
Please refer to the Supporting Information for more details.
-
-
-
-
55
-
-
35048903503
-
-
Z. Li, D. A. Capretto, R. O. Rahaman, C. He, J. Am. Chem. Soc. 2007, 129, 12058.
-
(2007)
J. Am. Chem. Soc
, vol.129
, pp. 12058
-
-
Li, Z.1
Capretto, D.A.2
Rahaman, R.O.3
He, C.4
-
56
-
-
0037415080
-
-
F. Ragaini, A. Penoni, E. Gallo, S. Tollari, C. L. Gotti, M. Lapadula, E. Mangioni, S. Cenini, Chem. Eur. J. 2003, 9, 249.
-
(2003)
Chem. Eur. J
, vol.9
, pp. 249
-
-
Ragaini, F.1
Penoni, A.2
Gallo, E.3
Tollari, S.4
Gotti, C.L.5
Lapadula, M.6
Mangioni, E.7
Cenini, S.8
-
59
-
-
37049069875
-
-
b) H. Takeuchi, M. Maeda, M. Mitani, K. Koyama, J. Chem. Soc. Perkin Trans. 1 1987, 57.
-
(1987)
J. Chem. Soc. Perkin Trans. 1
, pp. 57
-
-
Takeuchi, H.1
Maeda, M.2
Mitani, M.3
Koyama, K.4
-
60
-
-
33846430525
-
-
II-mediated nitrogen atom transfer from iminoiodinanes, see: a K. W. Fiori, J. Du Bois, J. Am. Chem. Soc. 2007, 129, 562;
-
II-mediated nitrogen atom transfer from iminoiodinanes, see: a) K. W. Fiori, J. Du Bois, J. Am. Chem. Soc. 2007, 129, 562;
-
-
-
-
61
-
-
38349004623
-
-
b) C. Liang, F. Collet, F. Robert-Peillard, P. Müller, R. H. Dodd, P. Dauban, J. Am. Chem. Soc. 2008, 130, 343.
-
(2008)
J. Am. Chem. Soc
, vol.130
, pp. 343
-
-
Liang, C.1
Collet, F.2
Robert-Peillard, F.3
Müller, P.4
Dodd, R.H.5
Dauban, P.6
-
62
-
-
53549087134
-
-
For reports of Lewis acid coordination to the α-nitrogen atom of an azide, see: a
-
For reports of Lewis acid coordination to the α-nitrogen atom of an azide, see: a) ref. [25b];
-
-
-
-
63
-
-
0001056137
-
-
b) G. A. Olah, P. Ramaiah, Q. Wang, G. K. S. Prakash, J. Org. Chem. 1993, 58, 6900;
-
(1993)
J. Org. Chem
, vol.58
, pp. 6900
-
-
Olah, G.A.1
Ramaiah, P.2
Wang, Q.3
Prakash, G.K.S.4
-
66
-
-
0034698586
-
-
b) H. V. R. Dias, S. A. Polach, S.-K. Goh, E. F. Archibong, D. S. Marynick, Inorg. Chem. 2000, 39, 3894.
-
(2000)
Inorg. Chem
, vol.39
, pp. 3894
-
-
Dias, H.V.R.1
Polach, S.A.2
Goh, S.-K.3
Archibong, E.F.4
Marynick, D.S.5
-
67
-
-
0037065710
-
-
II-mediated carbene transfer reactions, respectively, see: a M. C. Pirrung, H. Liu, A. T. Morehead, Jr., J. Am. Chem. Soc. 2002, 124, 1014;
-
II-mediated carbene transfer reactions, respectively, see: a) M. C. Pirrung, H. Liu, A. T. Morehead, Jr., J. Am. Chem. Soc. 2002, 124, 1014;
-
-
-
-
68
-
-
84961985018
-
-
b) E. Nakamura, N. Yoshikai, M. Yamanaka, J. Am. Chem. Soc. 2002, 124, 7181.
-
(2002)
J. Am. Chem. Soc
, vol.124
, pp. 7181
-
-
Nakamura, E.1
Yoshikai, N.2
Yamanaka, M.3
-
69
-
-
0346332616
-
-
In the related thermal nitrene C-H amination reaction, C-N bond formation is believed to precede N-H bond formation. See: P. A. S. Smith, C. D. Rowe, D. W. Hansen, Jr, Tetrahedron Lett. 1983, 24, 5169
-
In the related thermal nitrene C-H amination reaction, C-N bond formation is believed to precede N-H bond formation. See: P. A. S. Smith, C. D. Rowe, D. W. Hansen, Jr., Tetrahedron Lett. 1983, 24, 5169.
-
-
-
-
70
-
-
34447628388
-
-
For reviews of Lewis acid mediated Schmidt reactions involving azide additions to olefins, see: a
-
For reviews of Lewis acid mediated Schmidt reactions involving azide additions to olefins, see: a) W. R. Judd, C. E. Katz, J. Aubé, Sci. Synth. 2005, 21, 133;
-
(2005)
Sci. Synth
, vol.21
, pp. 133
-
-
Judd, W.R.1
Katz, C.E.2
Aubé, J.3
-
72
-
-
0001753841
-
-
4], see: M. P. Doyle, M. R. Colsman, M. S. Chinn, Inorg. Chem. 1984, 23, 3684.
-
4], see: M. P. Doyle, M. R. Colsman, M. S. Chinn, Inorg. Chem. 1984, 23, 3684.
-
-
-
-
73
-
-
53549096687
-
-
Similar results were obtained with alkyl-substituted azides. See the Supporting Information for more details
-
Similar results were obtained with alkyl-substituted azides. See the Supporting Information for more details.
-
-
-
-
74
-
-
53549107932
-
-
Neither [Rh2(O2CC3F7) 4] nor [Rh2(O2CC7H 15)4] were found to isomerize cis-stilbene under the reaction conditions
-
4] were found to isomerize cis-stilbene under the reaction conditions.
-
-
-
-
75
-
-
0001335692
-
-
Similar 1,2-phenyl shifts were observed in the thermolysis of related β,β-disubstituted styryl azides (reference [30]) as well as phosphine-mediated deoxygenation reactions of the corresponding nitro compounds (R. J. Sundberg, T. Yamazaki, J. Org. Chem. 1967, 32, 290).
-
Similar 1,2-phenyl shifts were observed in the thermolysis of related β,β-disubstituted styryl azides (reference [30]) as well as phosphine-mediated deoxygenation reactions of the corresponding nitro compounds (R. J. Sundberg, T. Yamazaki, J. Org. Chem. 1967, 32, 290).
-
-
-
-
76
-
-
53549099280
-
-
Attempts to trap cation 16 through the addition of allyltrimethylsilane or allyltributylstannane were not successful.
-
Attempts to trap cation 16 through the addition of allyltrimethylsilane or allyltributylstannane were not successful.
-
-
-
|