-
1
-
-
85041520295
-
-
a) Handbook of C-H Transformations, (Ed.: G. Dyker), Wiley-VCH, Weinheim, 2005;
-
-
-
-
5
-
-
35248816863
-
-
For recent reviews on C-H activation/hydroarylation. see: a) L. Ackermann, Top. Organomet. Chem. 2008, 24, 35-60;
-
(2008)
Top. Organomet. Chem.
, vol.24
, pp. 35-60
-
-
Ackermann, L.1
-
6
-
-
33846918696
-
-
b) D. Alberico, M. E. Scott, M. Lautens, Chem. Rev. 2007, 107, 174-238:
-
(2007)
Chem. Rev.
, vol.107
, pp. 174-238
-
-
Alberico, D.1
Scott, M.E.2
Lautens, M.3
-
9
-
-
34547205815
-
-
Ed.: O. Dyker, Wiley-VCH, Weinheim
-
For representative homo-hydroalkynylations (sell-couplings of terminal alkynes), see: a) E. Bustelo, P. H. Dixneuf, in Handbook of CH Transformations, (Ed.: O. Dyker), Wiley-VCH, Weinheim, 2005, p 62:
-
(2005)
Handbook of CH Transformations
, pp. 62
-
-
Bustelo, E.1
Dixneuf, P.H.2
-
10
-
-
0013165841
-
-
b) Y. Nishibayashi. M. Yamanashi, I. Wakiji, M. Hidai. Angew. Chem. 2000, 112, 3031 -3033;
-
(2000)
Angew. Chem.
, vol.112
, pp. 3031-3033
-
-
Nishibayashi, Y.1
Yamanashi, M.2
Wakiji, I.3
Hidai, M.4
-
11
-
-
0034683054
-
-
Angew. Chem. Int. Ed. 2000, 39, 2909-2911:
-
(2000)
Angew. Chem. Int. Ed.
, vol.39
, pp. 2909-2911
-
-
-
13
-
-
0037419829
-
-
d) M. Nishiura, Z. Hou, Y. Wakatsuki. T. Yamaki, T. Miyamoto. J. Am. Chem. Soc. 2003, 125, 1184-1185;
-
(2003)
J. Am. Chem. Soc.
, vol.125
, pp. 1184-1185
-
-
Nishiura, M.1
Hou, Z.2
Wakatsuki, Y.3
Yamaki, T.4
Miyamoto, T.5
-
15
-
-
33645452006
-
-
f) W. Weng. C. Guo, R. Çelenligil-Çetin. B. M. Foxman, O. V. Ozerov, Chem. Commun. 2006, 197-199;
-
(2006)
Chem. Commun.
, pp. 197-199
-
-
Weng, W.1
Guo, C.2
Çelenligil-Çetin, R.3
Foxman, B.M.4
Ozerov, O.V.5
-
16
-
-
33846611597
-
-
g) R. Ghosh, X. Zhang, P. Achord, T. J. Emge. K. Krogh-Jespersen, A. S. Goldman, J. Am. Chem. Soc. 2007, 129, 853-856.
-
(2007)
J. Am. Chem. Soc.
, vol.129
, pp. 853-856
-
-
Ghosh, R.1
Zhang, X.2
Achord, P.3
Emge, T.J.4
Krogh-Jespersen, K.5
Goldman, A.S.6
-
17
-
-
0030970084
-
-
For cross-hydroalkynylations (additions of a terminal alkyne to a different alkyne molecule), see: Pd-catalyzed: a) B. M. Trost. M.C. McIntosh, Tetrahedron Lett. 1997, 38, 3207-3210;
-
(1997)
Tetrahedron Lett.
, vol.38
, pp. 3207-3210
-
-
Trost, B.M.1
McIntosh, M.C.2
-
18
-
-
0031046817
-
-
b) B. M. Trost, M. T. Sorum. C. Chan, A. E. Harms, G. Rühter, J. Am. Chem. Soc. 1997, 119, 698-708;
-
(1997)
J. Am. Chem. Soc.
, vol.119
, pp. 698-708
-
-
Trost, B.M.1
Sorum, M.T.2
Chan, C.3
Harms, A.E.4
Rühter, G.5
-
21
-
-
34250854315
-
-
e) S. Kamijo, Y. Sasaki, C. Kanazawa, T. Schüßeler. Y. Yamamoto, Angew. Chem. 2005, 117, 7896-7899;
-
(2005)
Angew. Chem.
, vol.117
, pp. 7896-7899
-
-
Kamijo, S.1
Sasaki, Y.2
Kanazawa, C.3
Schüßeler, T.4
Yamamoto, Y.5
-
22
-
-
28744455408
-
-
Angew. Chem. Int. Ed. 2005, 44, 7718-7721;
-
(2005)
Angew. Chem. Int. Ed.
, vol.44
, pp. 7718-7721
-
-
-
23
-
-
34547163896
-
-
f) N. Tsukada, S. Ninomiya, Y. Aoyama, Y. Inoue, Org. Lett. 2007, 9, 2919-2921; Rh-calalyzed:
-
(2007)
Org. Lett.
, vol.9
, pp. 2919-2921
-
-
Tsukada, N.1
Ninomiya, S.2
Aoyama, Y.3
Inoue, Y.4
-
24
-
-
34547184427
-
-
g) T. Katagiri. H. Tsurugi, A. Funayama, T. Satoh, M. Miura, Chem. Lett. 2007, 36, 830-831;
-
(2007)
Chem. Lett.
, vol.36
, pp. 830-831
-
-
Katagiri, T.1
Tsurugi, H.2
Funayama, A.3
Satoh, T.4
Miura, M.5
-
25
-
-
37349118689
-
-
h) T. Nishimura. X.-X. Guo, K. Ohnishi, T. Hayashi, Adv. Synth. Catal. 2007, 349, 2669-2672;
-
(2007)
Adv. Synth. Catal.
, vol.349
, pp. 2669-2672
-
-
Nishimura, T.1
Guo, X.-X.2
Ohnishi, K.3
Hayashi, T.4
-
27
-
-
20044373868
-
-
j) T. Hirabayashi, S. Sakaguchi, Y. Ishii, Adv. Synth. Catal. 2005, 347, 872-876: Ru-calalyzed:
-
(2005)
Adv. Synth. Catal.
, vol.347
, pp. 872-876
-
-
Hirabayashi, T.1
Sakaguchi, S.2
Ishii, Y.3
-
30
-
-
68149093550
-
-
m) K. Ogata, H. Murayama, J. Sugasawa, N. Suzuki, S. Fukuzawa, J. Am. Chem. Soc. 2009, 131, 3176-3177.
-
(2009)
J. Am. Chem. Soc.
, vol.131
, pp. 3176-3177
-
-
Ogata, K.1
Murayama, H.2
Sugasawa, J.3
Suzuki, N.4
Fukuzawa, S.5
-
32
-
-
0028136763
-
-
b) M. Yamaguchi, K. Omata, M. Hirama, Tetrahedron Lett. 1994, 35, 5689-5692;
-
(1994)
Tetrahedron Lett.
, vol.35
, pp. 5689-5692
-
-
Yamaguchi, M.1
Omata, K.2
Hirama, M.3
-
33
-
-
0142216175
-
-
c) D. Bruyere. R. Grigg. J. Hinsley, R. K. Hussain, S. Korn. C. O. de La Cierva, V. Sridharan, J. Wang. Tetrahedron Lett. 2003, 44, 8669-8676:
-
(2003)
Tetrahedron Lett.
, vol.44
, pp. 8669-8676
-
-
Bruyere, D.1
Grigg, R.2
Hinsley, J.3
Hussain, R.K.4
Korn, S.5
De La Cierva, C.O.6
Sridharan, V.7
Wang, J.8
-
34
-
-
0041529949
-
-
d) M. Rubin. J. Markov. S. Chuprakov. D.J. Wink. V. Gevorgyan, J.Org. Chem. 2003, 68, 6251-6256.
-
(2003)
J.Org. Chem.
, vol.68
, pp. 6251-6256
-
-
Rubin, M.1
Markov, J.2
Chuprakov, S.3
Wink, D.J.4
Gevorgyan, V.5
-
36
-
-
77950860429
-
-
b) K. Kohno, K. Nakagawa. T. Yahagi, J-C. Choi, H. Yasuda, T. Sakakura, J. Am. Chem. Soc. 2009, 131, 2784-2785;
-
(2009)
J. Am. Chem. Soc.
, vol.131
, pp. 2784-2785
-
-
Kohno, K.1
Nakagawa, K.2
Yahagi, T.3
Choi, J.-C.4
Yasuda, H.5
Sakakura, T.6
-
37
-
-
61349083559
-
-
c) T. Nishimura, E. Tsurumaki, T. Kawamoto. X-X. Guo, T. Hayashi, Org. Lett. 2008, 10, 4057-4060.
-
(2008)
Org. Lett.
, vol.10
, pp. 4057-4060
-
-
Nishimura, T.1
Tsurumaki, E.2
Kawamoto, T.3
Guo, X.-X.4
Hayashi, T.5
-
41
-
-
3042601278
-
-
d) T. Nishimura, Y. Washilake, Y. Nishiguchi, Y. Maeda. S. Uemura, Chem. Commun. 2004, 1312-1313;
-
(2004)
Chem. Commun.
, pp. 1312-1313
-
-
Nishimura, T.1
Washilake, Y.2
Nishiguchi, Y.3
Maeda, Y.4
Uemura, S.5
-
42
-
-
38949195266
-
-
e) T. Nishimura. X-X. Guo, N. Uchiyama. T. Katoh, T Hayashi, J. Am. Chem. Soc. 2008, 130, 1576-1577.
-
(2008)
J. Am. Chem. Soc.
, vol.130
, pp. 1576-1577
-
-
Nishimura, T.1
Guo, X.-X.2
Uchiyama, N.3
Katoh, T.4
Hayashi, T.5
-
46
-
-
33750167114
-
-
For the catalytic addition of terminal alkynes to carbon-heleroatom bonds, such as imines and aldehydes, see: a) L. Zani. C. Bolm, Chem. Commun. 2006, 4263-4275 and references therein;
-
(2006)
Chem. Commun.
, pp. 4263-4275
-
-
Zani, L.1
Bolm, C.2
-
48
-
-
33847676480
-
-
c) Y. Kuninobu, Y. Inoue, K. Takai, Chem. Lett. 2006, 35, 1376-1377;
-
(2006)
Chem. Lett.
, vol.35
, pp. 1376-1377
-
-
Kuninobu, Y.1
Inoue, Y.2
Takai, K.3
-
49
-
-
33644506744
-
-
d) J.-X. Ji, J. Wu, L. Xu, C.-W. Yip, K. H. Lam, A. S. C. Chan, Pure Appl. Chem. 2006, 78, 267-274 and references therein.
-
(2006)
Pure Appl. Chem.
, vol.78
, pp. 267-274
-
-
Ji, J.-X.1
Wu, J.2
Xu, L.3
Yip, C.-W.4
Lam, K.H.5
Chan, A.S.C.6
-
50
-
-
34547444477
-
-
For recent reviews, see: a) M. Rubin, M. Rubina, V. Gevorgyan, Chem. Rev. 2007, 107, 3117-3179;
-
(2007)
Chem. Rev.
, vol.107
, pp. 3117-3179
-
-
Rubin, M.1
Rubina, M.2
Gevorgyan, V.3
-
51
-
-
0038640190
-
-
b) A. Brandi, S. Cicchi, F. M. Cordero, A. Goti, Chem. Rev. 2003, 103, 1213-1270.
-
(2003)
Chem. Rev.
, vol.103
, pp. 1213-1270
-
-
Brandi, A.1
Cicchi, S.2
Cordero, F.M.3
Goti, A.4
-
52
-
-
0001500173
-
-
For a review on transition-metal-catalyzed reactions of methylenecyclopropenes, see: I. Nakamura, Y. Yamamoto, Adv. Synth. Catal. 2002, 544, 111-129.
-
(2002)
Adv. Synth. Catal.
, vol.544
, pp. 111-129
-
-
Nakamura, I.1
Yamamoto, Y.2
-
53
-
-
0001147723
-
-
For examples on [3+2] cycloadditions, see: a) R. Noyori, T. Odagi, H. Takaya, J. Am. Chem. Soc. 1970, 92, 5780-5781;
-
(1970)
J. Am. Chem. Soc.
, vol.92
, pp. 5780-5781
-
-
Noyori, R.1
Odagi, T.2
Takaya, H.3
-
55
-
-
0010610608
-
-
c) P. Binger, Q.-H. Lu, P. Wedemann, Angew. Chem. 1985, 97, 333-334;
-
(1985)
Angew. Chem.
, vol.97
, pp. 333-334
-
-
Binger, P.1
Lu, Q.-H.2
Wedemann, P.3
-
58
-
-
0028820203
-
-
e) M. Lautens, Y. Ren, P. Delanghe, P. Chiu, S. Ma, J. Colucci, Can. J. Chem. 1995, 73, 1251-1257;
-
(1995)
Can. J. Chem.
, vol.73
, pp. 1251-1257
-
-
Lautens, M.1
Ren, Y.2
Delanghe, P.3
Chiu, P.4
Ma, S.5
Colucci, J.6
-
59
-
-
29544446357
-
-
f) I. Nakamura, B. Ho Oh, S. Saito, Y. Yamamoto, Angew. Chem. 2001, 113, 1338-1340;
-
(2001)
Angew. Chem.
, vol.113
, pp. 1338-1340
-
-
Nakamura, I.1
Ho, O.B.2
Saito, S.3
Yamamoto, Y.4
-
60
-
-
0035794939
-
-
Angew. Chem. Int. Ed. 2001, 40, 1298-1300;
-
(2001)
Angew. Chem. Int. Ed.
, vol.40
, pp. 1298-1300
-
-
-
61
-
-
0043210690
-
-
g) A. Delgado, J. R. Rodríguez, L. Castedo, J. L. Mascareñas, J. Am. Chem. Soc. 2003, 125, 9282-9283;
-
(2003)
J. Am. Chem. Soc.
, vol.125
, pp. 9282-9283
-
-
Delgado, A.1
Rodríguez, J.R.2
Castedo, L.3
Mascareñas, J.L.4
-
62
-
-
4143094838
-
-
h) F. Lopez, A. Delgado, J. R. Rodríguez, L. Castedo, J. L. Mascareñas, J. Am. Chem. Soc. 2004, 126, 10262-10263;
-
(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 10262-10263
-
-
Lopez, F.1
Delgado, A.2
Rodríguez, J.R.3
Castedo, L.4
Mascareñas, J.L.5
-
63
-
-
2142652134
-
-
i) A. I. Siriwardana, I. Nakamura, Y. Yamamoto, J.Org. Chem. 2004, 69, 3202-3204;
-
(2004)
J.Org. Chem.
, vol.69
, pp. 3202-3204
-
-
Siriwardana, A.I.1
Nakamura, I.2
Yamamoto, Y.3
-
64
-
-
29444443618
-
-
j) J. Duran, M. Gulías, L. Castedo, J. L. Mascareñas, Org. Lett. 2005, 7, 5693-5696;
-
(2005)
Org. Lett.
, vol.7
, pp. 5693-5696
-
-
Duran, J.1
Gulías, M.2
Castedo, L.3
Mascareñas, J.L.4
-
65
-
-
33845277146
-
-
k) B. Trillo, M. Gulías, F. López, L. Castedo, J. L. Mascareñas, Adv. Synth. Catal. 2006, 348, 2381-2384;
-
(2006)
Adv. Synth. Catal.
, vol.348
, pp. 2381-2384
-
-
Trillo, B.1
Gulías, M.2
López, F.3
Castedo, L.4
Mascareñas, J.L.5
-
66
-
-
31544445030
-
-
M. Gulías, R. García, A. Delgado, L. Castedo, J. L. Mascareñas, J. Am. Chem. Soc. 2006, 128, 384-385.
-
(2006)
J. Am. Chem. Soc.
, vol.128
, pp. 384-385
-
-
Gulías, M.1
García, R.2
Delgado, A.3
Castedo, L.4
Mascareñas, J.L.5
-
67
-
-
34548711324
-
-
For examples on [3+4] cycloadditions, see: a) M. Gulías, J. Duran, F. López, L. Castedo, J. L. Mascareñas, J. Am. Chem. Soc. 2007, 129, 11026-11027;
-
(2007)
J. Am. Chem. Soc.
, vol.129
, pp. 11026-11027
-
-
Gulías, M.1
Duran, J.2
López, F.3
Castedo, L.4
Mascareñas, J.L.5
-
69
-
-
84982076350
-
-
For examples on [3+2+2] cycloadditions, see: a) P. Binger, U. Schuchardt, Chem. Ber. 1980, 113, 1063-1071;
-
(1980)
Chem. Ber.
, vol.113
, pp. 1063-1071
-
-
Binger, P.1
Schuchardt, U.2
-
70
-
-
4344715554
-
-
b) S. Saito, M. Masuda, S. Komagawa, J. Am. Chem. Soc. 2004, 126, 10540-10541;
-
(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 10540-10541
-
-
Saito, S.1
Masuda, M.2
Komagawa, S.3
-
73
-
-
33746305290
-
-
Angew. Chem. Int. Ed. 2006, 45, 2446-2449;
-
(2006)
Angew. Chem. Int. Ed.
, vol.45
, pp. 2446-2449
-
-
-
74
-
-
36649024106
-
-
e) S. Saito, S. Komagawa, I. Azumaya, M. Masuda, J. Org. Chem. 2007, 72, 9114-9120;
-
(2007)
J. Org. Chem.
, vol.72
, pp. 9114-9120
-
-
Saito, S.1
Komagawa, S.2
Azumaya, I.3
Masuda, M.4
-
77
-
-
58749109592
-
-
h) R. Yamasaki, I. Sotome, S. Komagawa, I. Azumaya, H. Masu, S. Saito, Tetrahedron Lett. 2009, 50, 1143-1145.
-
(2009)
Tetrahedron Lett.
, vol.50
, pp. 1143-1145
-
-
Yamasaki, R.1
Sotome, I.2
Komagawa, S.3
Azumaya, I.4
Masu, H.5
Saito, S.6
-
79
-
-
0030794889
-
-
b) N. Tsukada, A. Shibuya, I. Nakamura, Y. Yamamoto, J. Am. Chem. Soc. 1997, 119, 8123-8124;
-
(1997)
J. Am. Chem. Soc.
, vol.119
, pp. 8123-8124
-
-
Tsukada, N.1
Shibuya, A.2
Nakamura, I.3
Yamamoto, Y.4
-
80
-
-
0000373069
-
-
c) D. H. Camacho, I. Nakamura, S. Saito, Y. Yamamoto, Angew. Chem. 1999, 111, 3576-3578;
-
(1999)
Angew. Chem.
, vol.111
, pp. 3576-3578
-
-
Camacho, D.H.1
Nakamura, I.2
Saito, S.3
Yamamoto, Y.4
-
81
-
-
0033571256
-
-
Angew. Chem. Int. Ed. 1999, 38, 3365-3367;
-
(1999)
Angew. Chem. Int. Ed.
, vol.38
, pp. 3365-3367
-
-
-
82
-
-
0034701226
-
-
d) I. Nakamura, S. Saito, Y. Yamamoto, J. Am. Chem. Soc. 2000, 122, 2661-2662;
-
(2000)
J. Am. Chem. Soc.
, vol.122
, pp. 2661-2662
-
-
Nakamura, I.1
Saito, S.2
Yamamoto, Y.3
-
83
-
-
0035847198
-
-
e) D. H. Camacho, I. Nakamura, S. Saito, S. Yamamoto, J.Org. Chem. 2001, 66, 270-275;
-
(2001)
J.Org. Chem.
, vol.66
, pp. 270-275
-
-
Camacho, D.H.1
Nakamura, I.2
Saito, S.3
Yamamoto, S.4
-
84
-
-
0037123585
-
-
f) I. Nakamura, A. I. Siriwardana, S. Saito, Y. Yamamoto, J. Org. Chem. 2002, 67, 3445-3449;
-
(2002)
J. Org. Chem.
, vol.67
, pp. 3445-3449
-
-
Nakamura, I.1
Siriwardana, A.I.2
Saito, S.3
Yamamoto, Y.4
-
85
-
-
0037090148
-
-
g) D. H. Camacho, I. Nakamura, B. Ho Oh, S. Saito, Y. Yamamoto, Tetrahedron Lett. 2002, 43, 2903-2907;
-
(2002)
Tetrahedron Lett.
, vol.43
, pp. 2903-2907
-
-
Camacho, D.H.1
Nakamura, I.2
Ho, O.B.3
Saito, S.4
Yamamoto, Y.5
-
86
-
-
0141628939
-
-
h) M. Shi, Y. Chem, B. Xu, Org. Lett. 2003, 5, 1225-1228;
-
(2003)
Org. Lett.
, vol.5
, pp. 1225-1228
-
-
Shi, M.1
Chem, Y.2
Xu, B.3
-
87
-
-
22244439169
-
-
i) A. I. Siriwardana, M. Kamada, I. Nakamura, Y. Yamamoto, J. Org. Chem. 2005, 70, 5932-5937.
-
(2005)
J. Org. Chem.
, vol.70
, pp. 5932-5937
-
-
Siriwardana, A.I.1
Kamada, M.2
Nakamura, I.3
Yamamoto, Y.4
-
88
-
-
85041520372
-
-
[13g, h]
-
-
-
-
89
-
-
85041525245
-
-
See Supporting Information for a list of results with other catalysts employed. "chemical equation presented"
-
-
-
-
90
-
-
85041529077
-
-
Regioisomers 3 and 4 were isolated together after standard chromatography. The minor isomer of type 5 could be separated from the mixture of 3 and 4 but it turned out to be slightly contaminated by L1 and other very minor reaction components. Therefore, yields refer to the mixture of the major components, 3 and 4.
-
-
-
-
91
-
-
85041499136
-
-
3] (6%) and L1 (20%), in the absence of 2a, led to the recovery of 1b [Eq. (2)]. "chemical equation presented"
-
-
-
-
92
-
-
85041516316
-
-
This type of isomerization process has been previously proposed in a related hyfrofunctionalization os ACPs, see reference [16e].
-
-
-
|