-
1
-
-
0037009990
-
-
For the synthesis of azacycles, see: a
-
For the synthesis of azacycles, see: a) H. Kusama, J. Takaya, N. Iwasawa, J. Am. Chem. Soc. 2002, 124, 11592;
-
(2002)
J. Am. Chem. Soc
, vol.124
, pp. 11592
-
-
Kusama, H.1
Takaya, J.2
Iwasawa, N.3
-
2
-
-
1342284726
-
-
b) J. Takaya, H. Kusama, N. Iwasawa, Chem. Lett. 2004, 33, 16;
-
(2004)
Chem. Lett
, vol.33
, pp. 16
-
-
Takaya, J.1
Kusama, H.2
Iwasawa, N.3
-
3
-
-
31544464934
-
-
c) H. Kusama, Y. Miyashita, J. Takaya, N. Iwasawa, Org. Lett. 2006, 8, 289;
-
(2006)
Org. Lett
, vol.8
, pp. 289
-
-
Kusama, H.1
Miyashita, Y.2
Takaya, J.3
Iwasawa, N.4
-
4
-
-
33644953224
-
-
d) H. Kusama, Y. Suzuki, J. Takaya, N. Iwasawa, Org. Lett. 2006, 8, 895;
-
(2006)
Org. Lett
, vol.8
, pp. 895
-
-
Kusama, H.1
Suzuki, Y.2
Takaya, J.3
Iwasawa, N.4
-
5
-
-
14744267835
-
-
for the synthesis of oxacycles, see: e
-
for the synthesis of oxacycles, see: e) H. Kusama, H. Funami, M. Shido, Y. Hara, J. Takaya, N. Iwasawa, J. Am. Chem. Soc. 2005, 127, 2709;
-
(2005)
J. Am. Chem. Soc
, vol.127
, pp. 2709
-
-
Kusama, H.1
Funami, H.2
Shido, M.3
Hara, Y.4
Takaya, J.5
Iwasawa, N.6
-
6
-
-
0034801531
-
-
f) N. Iwasawa, M. Shido, H. Kusama, J. Am. Chem. Soc. 2001, 123, 5814;
-
(2001)
J. Am. Chem. Soc
, vol.123
, pp. 5814
-
-
Iwasawa, N.1
Shido, M.2
Kusama, H.3
-
8
-
-
1342332893
-
-
h) H. Kusama, H. Funami, J. Takaya, N. Iwasawa, Org. Lett. 2004, 6, 605;
-
(2004)
Org. Lett
, vol.6
, pp. 605
-
-
Kusama, H.1
Funami, H.2
Takaya, J.3
Iwasawa, N.4
-
10
-
-
0004026247
-
-
Ed, J. S. Clark, Oxford University Press, Oxford
-
a) F. G. West, J. S. Clark in Nitrogen, Oxygen and Sulfur Ylide Chemistry (Ed.: J. S. Clark), Oxford University Press, Oxford, 2002, p. 115;
-
(2002)
Nitrogen, Oxygen and Sulfur Ylide Chemistry
, pp. 115
-
-
West, F.G.1
Clark, J.S.2
-
11
-
-
53549125421
-
-
Ed, J. S. Clark, Oxford University Press, Oxford
-
b) Y. Sato in Nitrogen, Oxygen and Sulfur Ylide Chemistry (Ed.: J. S. Clark), Oxford University Press, Oxford, 2002, p. 134;
-
(2002)
Nitrogen, Oxygen and Sulfur Ylide Chemistry
, pp. 134
-
-
Sato, Y.1
-
12
-
-
0004026247
-
-
Ed, J. S. Clark, Oxford University Press, Oxford
-
c) M. P. Doyle, D. C. Forbes in Nitrogen, Oxygen and Sulfur Ylide Chemistry (Ed.: J. S. Clark), Oxford University Press, Oxford, 2002, p. 141;
-
(2002)
Nitrogen, Oxygen and Sulfur Ylide Chemistry
, pp. 141
-
-
Doyle, M.P.1
Forbes, D.C.2
-
16
-
-
53249111171
-
-
G. Li, X. Huang, L. Zhang, Angew. Chem. 2008, 120, 352;
-
(2008)
Angew. Chem
, vol.120
, pp. 352
-
-
Li, G.1
Huang, X.2
Zhang, L.3
-
18
-
-
37049158339
-
-
a) T. S. Stevens, E. M. Creighton, A. B. Gordon, M. MacNicol, J. Chem. Soc. 1928, 3193;
-
(1928)
J. Chem. Soc
, pp. 3193
-
-
Stevens, T.S.1
Creighton, E.M.2
Gordon, A.B.3
MacNicol, M.4
-
19
-
-
29744470611
-
-
and references therein
-
b) J. A. Vanecko, H. Wan, F. G. West, Tetrahedron 2006, 62, 1043, and references therein.
-
(2006)
Tetrahedron
, vol.62
, pp. 1043
-
-
Vanecko, J.A.1
Wan, H.2
West, F.G.3
-
20
-
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53549103191
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This type of [1,2] Stevens-type rearrangement of ylide species A is unprecedented, except for the recent example reported by Zhang and co-workers of a 1,2-migration reaction of lactam derivatives. In the latter reaction, an acylium intermediate generated from the alkenyl metal intermediate is proposed as a key intermediate; see Ref, 3
-
This type of [1,2] Stevens-type rearrangement of ylide species A is unprecedented, except for the recent example reported by Zhang and co-workers of a 1,2-migration reaction of lactam derivatives. In the latter reaction, an acylium intermediate generated from the alkenyl metal intermediate is proposed as a key intermediate; see Ref. [3]
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-
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21
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34447503462
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For 1,3-migration reactions of allyl, methoxymethyl, acyl, and sulfonyl groups from alkenyl palladium or gold zwitterionic intermediates related to A, see: a I. Nakamura, Y. Mizushima, U. Yamagishi, Y. Yamamoto, Tetrahedron 2007, 63, 8670;
-
For 1,3-migration reactions of allyl, methoxymethyl, acyl, and sulfonyl groups from alkenyl palladium or gold zwitterionic intermediates related to A, see: a) I. Nakamura, Y. Mizushima, U. Yamagishi, Y. Yamamoto, Tetrahedron 2007, 63, 8670;
-
-
-
-
22
-
-
53549124569
-
-
b) I. Nakamura, U. Yamagishi, D. Song, S. Konta, Y. Yamamoto, Angew. Chem. 2007, 119, 23 3 4;
-
(2007)
Angew. Chem
, vol.119
, Issue.23
, pp. 3-4
-
-
Nakamura, I.1
Yamagishi, U.2
Song, D.3
Konta, S.4
Yamamoto, Y.5
-
25
-
-
4344572110
-
-
d) T. Shimada, I. Nakamura, Y. Yamamoto, J. Am. Chem. Soc. 2004, 126, 10546;
-
(2004)
J. Am. Chem. Soc
, vol.126
, pp. 10546
-
-
Shimada, T.1
Nakamura, I.2
Yamamoto, Y.3
-
27
-
-
38049016722
-
-
f) K. Cariou, B. Ronan, S. Mignani, L. Fensterbank, M. Malacria, Angew. Chem. 2007, 119, 1913;
-
(2007)
Angew. Chem
, vol.119
, pp. 1913
-
-
Cariou, K.1
Ronan, B.2
Mignani, S.3
Fensterbank, L.4
Malacria, M.5
-
29
-
-
0001242798
-
-
g) S. Cacchi, G. Fabrizi, P. Pace, J. Org. Chem. 1998, 63, 1001;
-
(1998)
J. Org. Chem
, vol.63
, pp. 1001
-
-
Cacchi, S.1
Fabrizi, G.2
Pace, P.3
-
30
-
-
35048879619
-
-
for the synthesis of 3-substituted benzofurans and benzothiophenes via related intermediates, see: h
-
for the synthesis of 3-substituted benzofurans and benzothiophenes via related intermediates, see: h) I. Nakamura, T. Sato, M. Terada, Y. Yamamoto, Org. Lett. 2007, 9, 4081;
-
(2007)
Org. Lett
, vol.9
, pp. 4081
-
-
Nakamura, I.1
Sato, T.2
Terada, M.3
Yamamoto, Y.4
-
31
-
-
35748950676
-
-
i) A. Fürstner, E. K. Heilmann, P. W. Davies, Angew. Chem. 2007, 119, 4844;
-
(2007)
Angew. Chem
, vol.119
, pp. 4844
-
-
Fürstner, A.1
Heilmann, E.K.2
Davies, P.W.3
-
33
-
-
34250840234
-
-
j) I. Nakamura, T. Sato, Y. Yamamoto, Angew. Chem. 2006, 118, 4585;
-
(2006)
Angew. Chem
, vol.118
, pp. 4585
-
-
Nakamura, I.1
Sato, T.2
Yamamoto, Y.3
-
35
-
-
27544457189
-
-
k) I. Nakamura, Y. Mizushima, Y. Yamamoto, J. Am. Chem. Soc. 2005, 127, 15022;
-
(2005)
J. Am. Chem. Soc
, vol.127
, pp. 15022
-
-
Nakamura, I.1
Mizushima, Y.2
Yamamoto, Y.3
-
36
-
-
0035814401
-
-
l) A. Fürstner, F. Stelzer, H. Szillat, J. Am. Chem. Soc. 2001, 123, 11863;
-
(2001)
J. Am. Chem. Soc
, vol.123
, pp. 11863
-
-
Fürstner, A.1
Stelzer, F.2
Szillat, H.3
-
37
-
-
0038081446
-
-
m) A. Fürstner, H. Szillat, F. Stelzer, J. Am. Chem. Soc. 2000, 122, 6785.
-
(2000)
J. Am. Chem. Soc
, vol.122
, pp. 6785
-
-
Fürstner, A.1
Szillat, H.2
Stelzer, F.3
-
38
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53549085587
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In entries 5 and 7 of Table 1, N-(4-X-butyl)-2-methylindole (X = Br or Cl), which probably resulted from a ring-opening reaction of the ylide A upon attack by a halide anion, was obtained in low yield (< 20%) along with recovered starting material.
-
In entries 5 and 7 of Table 1, N-(4-X-butyl)-2-methylindole (X = Br or Cl), which probably resulted from a ring-opening reaction of the ylide A upon attack by a halide anion, was obtained in low yield (< 20%) along with recovered starting material.
-
-
-
-
39
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27844463013
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Avast number of alkaloids have polycyclic indole skeletons; see: a
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Avast number of alkaloids have polycyclic indole skeletons; see: a) W. Gul, M. T. Hamann, Life Sci. 2005, 78, 442;
-
(2005)
Life Sci
, vol.78
, pp. 442
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Gul, W.1
Hamann, M.T.2
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41
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53549112639
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These substrates can be prepared readily through a Pd-catalyzed amination and Sonogashira coupling reaction of 1-bromo-2-iodobenzene
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These substrates can be prepared readily through a Pd-catalyzed amination and Sonogashira coupling reaction of 1-bromo-2-iodobenzene.
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-
-
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42
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53549096134
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Classical methods for the generation of ammonium ylides require the use of a strong base or a fluoride source to form the anion; see Ref, 2e,f
-
Classical methods for the generation of ammonium ylides require the use of a strong base or a fluoride source to form the anion; see Ref. [2e,f].
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43
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53549110394
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6], the product 14 was obtained in only 16% yield, and 51% of the starting material was recovered.
-
6], the product 14 was obtained in only 16% yield, and 51% of the starting material was recovered.
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-
-
-
44
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53549124000
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For examples of [ReX(CO)5]-catalyzed reactions (X, Cl, Br) through the electrophilic activation of alkynes, see: a) H. Kusama, H. Yamabe, Y. Onizawa, T. Hoshino, N. Iwasawa, Angew. Chem. 2005, 117, 472;
-
5]-catalyzed reactions (X = Cl, Br) through the electrophilic activation of alkynes, see: a) H. Kusama, H. Yamabe, Y. Onizawa, T. Hoshino, N. Iwasawa, Angew. Chem. 2005, 117, 472;
-
-
-
-
46
-
-
23844502616
-
-
b) L. L. Ouh, T. E. Müller, Y. K. Yan, J. Organomet. Chem. 2005, 690, 3774;
-
(2005)
J. Organomet. Chem
, vol.690
, pp. 3774
-
-
Ouh, L.L.1
Müller, T.E.2
Yan, Y.K.3
-
48
-
-
27644479913
-
-
and Ref, 1c, see also: d
-
see also: d) Y. Kuninobu, A. Kawata, K. Takai, Org. Lett. 2005, 7, 4823 and Ref. [1c].
-
(2005)
Org. Lett
, vol.7
, pp. 4823
-
-
Kuninobu, Y.1
Kawata, A.2
Takai, K.3
-
49
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0011438041
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Metal carbenoids are well known to insert readily into the Si-H bond of silanes, even intermolecularly; see: a
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Metal carbenoids are well known to insert readily into the Si-H bond of silanes, even intermolecularly; see: a) J. A. Connor, P. D. Rose, R. M. Turner, J. Organomet. Chem. 1973, 55, 111;
-
(1973)
J. Organomet. Chem
, vol.55
, pp. 111
-
-
Connor, J.A.1
Rose, P.D.2
Turner, R.M.3
-
50
-
-
37049100840
-
-
J. A. Connor, J. P. Day, R. M. Turner, J. Chem. Soc. Dalton Trans. 1976, 108; see also Ref. [1e].
-
b) J. A. Connor, J. P. Day, R. M. Turner, J. Chem. Soc. Dalton Trans. 1976, 108; see also Ref. [1e].
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51
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53549113221
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Although the exact mechanism of the present [1,2] Stevens-type rearrangement is not yet clear, the ring expansion with cationic intermediates proposed by Zhang and co-workers[3] seems less likely in our case, as primary alkyl cations, which are not usually generated in a nonpolar solvent, such as toluene, must be involved. Furthermore, the formation of Friedel-Crafts-type products, which are side products in the reaction described by Zhang and co-workers, was not observed in our reaction
-
[3] seems less likely in our case, as primary alkyl cations, which are not usually generated in a nonpolar solvent, such as toluene, must be involved. Furthermore, the formation of Friedel-Crafts-type products, which are side products in the reaction described by Zhang and co-workers, was not observed in our reaction.
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