-
9
-
-
0000134380
-
-
Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford
-
(b) Soderberg, B. C. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 12, p 241.
-
(1995)
Comprehensive Organometallic Chemistry II
, vol.12
, pp. 241
-
-
Soderberg, B.C.1
-
10
-
-
7044235861
-
-
(a) Negishi, E.; Copéret, C.; Ma, S.; Liou, S.-Y.; Liu, F. Chem. Rev. 1996, 96, 365.
-
(1996)
Chem. Rev.
, vol.96
, pp. 365
-
-
Negishi, E.1
Copéret, C.2
Ma, S.3
Liou, S.-Y.4
Liu, F.5
-
16
-
-
0000379185
-
-
(a) Quan, L. G.; Lamrani, M.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 4827.
-
(2000)
J. Am. Chem. Soc.
, vol.122
, pp. 4827
-
-
Quan, L.G.1
Lamrani, M.2
Yamamoto, Y.3
-
17
-
-
0034699554
-
-
(b) Gai, X.; Grigg, R.; Collard, S.; Muir, J. E. Chem. Commun. 2000, 1765.
-
(2000)
Chem. Commun.
, pp. 1765
-
-
Gai, X.1
Grigg, R.2
Collard, S.3
Muir, J.E.4
-
18
-
-
0000913941
-
-
(c) Larock, R. C.; Doty, M. J.; Cacchi, S. J. Org. Chem. 1993, 58, 4579.
-
(1993)
J. Org. Chem.
, vol.58
, pp. 4579
-
-
Larock, R.C.1
Doty, M.J.2
Cacchi, S.3
-
19
-
-
0029042650
-
-
(d) Larock, R. C.; Yum, E. K.; Doty, M. J.; Sham, K. K. C. J. Org. Chem. 1995, 60, 3270.
-
(1995)
J. Org. Chem.
, vol.60
, pp. 3270
-
-
Larock, R.C.1
Yum, E.K.2
Doty, M.J.3
Sham, K.K.C.4
-
20
-
-
0033591176
-
-
(e) Gevorgian, V.; Quan, L. G.; Yamamoto, Y. Tetrahedron Lett. 1999, 40, 4089.
-
(1999)
Tetrahedron Lett.
, vol.40
, pp. 4089
-
-
Gevorgian, V.1
Quan, L.G.2
Yamamoto, Y.3
-
22
-
-
0000322361
-
-
For an example of the solvent nitrile incorporation into the product without involving carbopalladation of the cyano group, see: Hegedus, L. S.; Mulhern, T. A.; Asada, H. J. Am. Chem. Soc. 1986, 108, 6224.
-
(1986)
J. Am. Chem. Soc.
, vol.108
, pp. 6224
-
-
Hegedus, L.S.1
Mulhern, T.A.2
Asada, H.3
-
24
-
-
0035903934
-
-
and references therein
-
(b) Sundermeier, M.; Zapf, A.; Beller, M.; Sans, J. Tetrahedron Lett. 2001, 42, 6707 and references therein.
-
(2001)
Tetrahedron Lett.
, vol.42
, pp. 6707
-
-
Sundermeier, M.1
Zapf, A.2
Beller, M.3
Sans, J.4
-
25
-
-
0033584917
-
-
(c) Maligres, P. E.; Waters, M. S.; Fleitz, F.; Askin, D. Tetrahedron Lett. 1999, 40, 8193.
-
(1999)
Tetrahedron Lett.
, vol.40
, pp. 8193
-
-
Maligres, P.E.1
Waters, M.S.2
Fleitz, F.3
Askin, D.4
-
28
-
-
33845279444
-
-
(a) Chatani, N.; Takeyasu, T.; Horiuchi, N.; Hanafusa, T. J. Org. Chem. 1988, 53, 3539.
-
(1988)
J. Org. Chem.
, vol.53
, pp. 3539
-
-
Chatani, N.1
Takeyasu, T.2
Horiuchi, N.3
Hanafusa, T.4
-
29
-
-
0028027836
-
-
(b) Suginome, M.; Kinugasa, H.; Ito, Y. Tetrahedron Lett. 1994, 35, 8635.
-
(1994)
Tetrahedron Lett.
, vol.35
, pp. 8635
-
-
Suginome, M.1
Kinugasa, H.2
Ito, Y.3
-
30
-
-
0026631746
-
-
(a) Sakamoto, T.; Shiga, F.; Yasuhara, A.; Uchiyama, D.; Kondo, Y.; Yamanaka, H. Synthesis 1992, 746.
-
(1992)
Synthesis
, vol.746
-
-
Sakamoto, T.1
Shiga, F.2
Yasuhara, A.3
Uchiyama, D.4
Kondo, Y.5
Yamanaka, H.6
-
31
-
-
0030032580
-
-
(b) Bumagin, N. A.; Sukhomlinova, L. I.; Luzikova, E. V.; Tolstaya, T. P.; Beletskaya, I. P. Tetrahedron Lett. 1996, 37, 897.
-
(1996)
Tetrahedron Lett.
, vol.37
, pp. 897
-
-
Bumagin, N.A.1
Sukhomlinova, L.I.2
Luzikova, E.V.3
Tolstaya, T.P.4
Beletskaya, I.P.5
-
32
-
-
85004332547
-
-
(c) Sakamoto, T.; Kondo, Y.; Yamanaka, H. Chem. Pharm. Bull. 1985, 33, 626.
-
(1985)
Chem. Pharm. Bull.
, vol.33
, pp. 626
-
-
Sakamoto, T.1
Kondo, Y.2
Yamanaka, H.3
-
33
-
-
0345891233
-
-
(a) Kosugi, M.; Ishiguro, Y.; Negishi, Y.; Sano, H.; Migita, T. Chem. Lett. 1984, 1511.
-
(1984)
Chem. Lett.
, pp. 1511
-
-
Kosugi, M.1
Ishiguro, Y.2
Negishi, Y.3
Sano, H.4
Migita, T.5
-
36
-
-
0001363192
-
-
(d) Piber, M.; Jensen, A. E.; Rottländer, M.; Knochel, P. Org. Lett. 1999, 1, 1323.
-
(1999)
Org. Lett.
, vol.1
, pp. 1323
-
-
Piber, M.1
Jensen, A.E.2
Rottländer, M.3
Knochel, P.4
-
37
-
-
0030567369
-
-
Sawamura, M.; Sudoh, M.; Ito, Y. J. Am. Chem. Soc. 1996, 118, 3309.
-
(1996)
J. Am. Chem. Soc.
, vol.118
, pp. 3309
-
-
Sawamura, M.1
Sudoh, M.2
Ito, Y.3
-
38
-
-
85021672004
-
-
Minami, I.; Nisar, M.; Yuhara, M.; Shimizu, I.; Tsuji, J. Synthesis 1987, 992.
-
(1987)
Synthesis
, pp. 992
-
-
Minami, I.1
Nisar, M.2
Yuhara, M.3
Shimizu, I.4
Tsuji, J.5
-
40
-
-
0030699461
-
-
(b) Hénin, F.; Létinois, S.; Muzart, J. Tetrahedron Lett. 1997, 38, 7187.
-
(1997)
Tetrahedron Lett.
, vol.38
, pp. 7187
-
-
Hénin, F.1
Létinois, S.2
Muzart, J.3
-
41
-
-
0034685249
-
-
(c) Wei, L.-M.; Lin, C.-F.; Wu, M.-J. Tetrahedron Lett. 2000, 41, 1215.
-
(2000)
Tetrahedron Lett.
, vol.41
, pp. 1215
-
-
Wei, L.-M.1
Lin, C.-F.2
Wu, M.-J.3
-
42
-
-
33748596388
-
-
(a) Yang, C.-C.; Tai, H.-M.; Sun, P.-J. J. Chem. Soc., Perkin Trans. 1 1997, 2843.
-
(1997)
J. Chem. Soc., Perkin Trans. 1
, pp. 2843
-
-
Yang, C.-C.1
Tai, H.-M.2
Sun, P.-J.3
-
43
-
-
0000816812
-
-
(b) Deng, J.-H.; Tai, H.-M.; Yang, C.-C. J. Chin. Chem. Soc. 2000, 47, 327.
-
(2000)
J. Chin. Chem. Soc.
, vol.47
, pp. 327
-
-
Deng, J.-H.1
Tai, H.-M.2
Yang, C.-C.3
-
44
-
-
0001422138
-
-
Luo, F.-H.; Chu, C.-I.; Cheng, C.-H. Organometallics 1998, 17, 1025.
-
(1998)
Organometallics
, vol.17
, pp. 1025
-
-
Luo, F.-H.1
Chu, C.-I.2
Cheng, C.-H.3
-
45
-
-
0033531732
-
-
Larock, R. C.; Tian, Q.; Pletnev, A. A. J. Am. Chem. Soc. 1999, 121, 3238.
-
(1999)
J. Am. Chem. Soc.
, vol.121
, pp. 3238
-
-
Larock, R.C.1
Tian, Q.2
Pletnev, A.A.3
-
46
-
-
0001891898
-
-
American Chemical Society: Washington, DC
-
(a) Jourdan, G. P.; Dreikorn, B. A.; Hackler, R. E.; Hall, H. R.; Arnold, W. R. In Synthesis and Chemistry of Agrochemicals II; ACS Symposium Series; American Chemical Society: Washington, DC, 1991; p 566.
-
(1991)
Synthesis and Chemistry of Agrochemicals II; ACS Symposium Series
, pp. 566
-
-
Jourdan, G.P.1
Dreikorn, B.A.2
Hackler, R.E.3
Hall, H.R.4
Arnold, W.R.5
-
47
-
-
0002669698
-
-
(b) Frank, R. L.; Eklund, H.; Richter, J. W.; Vanneman, C. R.; Wennerberg, A. N. J. Am. Chem. Soc. 1944, 66, 1.
-
(1944)
J. Am. Chem. Soc.
, vol.66
, pp. 1
-
-
Frank, R.L.1
Eklund, H.2
Richter, J.W.3
Vanneman, C.R.4
Wennerberg, A.N.5
-
48
-
-
0024511965
-
-
(a) Anstead, G. M.; Ensign, J. L.; Peterson, C. S.; Katzenellenbogen, J. A. J. Org. Chem. 1989, 54, 1485.
-
(1989)
J. Org. Chem.
, vol.54
, pp. 1485
-
-
Anstead, G.M.1
Ensign, J.L.2
Peterson, C.S.3
Katzenellenbogen, J.A.4
-
49
-
-
0033096995
-
-
(b) Gao, H.; Katzenellenbogen, J. A.; Garg, R.; Hansch, C. Chem. Rev. 1999, 99, 723.
-
(1999)
Chem. Rev.
, vol.99
, pp. 723
-
-
Gao, H.1
Katzenellenbogen, J.A.2
Garg, R.3
Hansch, C.4
-
50
-
-
0000543304
-
-
and references therein
-
(a) Vicente, J.; Abad, J.-A.; Gil-Rubio, J. Organometallics 1996, 15, 3509, and references therein.
-
(1996)
Organometallics
, vol.15
, pp. 3509
-
-
Vicente, J.1
Abad, J.-A.2
Gil-Rubio, J.3
-
51
-
-
37049108384
-
-
(b) Buggle, K.; Ghogain, U. N.; O'Sullivan, D. J. Chem. Soc., Perkin Trans. 1 1983, 2075.
-
(1983)
J. Chem. Soc., Perkin Trans. 1
, pp. 2075
-
-
Buggle, K.1
Ghogain, U.N.2
O'Sullivan, D.3
-
52
-
-
0000379133
-
-
and references therein
-
Galatsis, P.; Manwell, J. J.; Blackwell, J. M. Can. J. Chem. 1994, 72, 1656 and references therein.
-
(1994)
Can. J. Chem.
, vol.72
, pp. 1656
-
-
Galatsis, P.1
Manwell, J.J.2
Blackwell, J.M.3
-
53
-
-
0035114355
-
-
For the most recent example, see: Hauser, F. M.; Zhou, M.; Sun, Y. Synth. Commun. 2001, 31, 77.
-
(2001)
Synth. Commun.
, vol.31
, pp. 77
-
-
Hauser, F.M.1
Zhou, M.2
Sun, Y.3
-
55
-
-
0035977241
-
-
(b) Roesch, K. R.; Zhang, H.; Larock, R. C. J. Org. Chem. 2001, 66, 8042.
-
(2001)
J. Org. Chem.
, vol.66
, pp. 8042
-
-
Roesch, K.R.1
Zhang, H.2
Larock, R.C.3
-
60
-
-
0033607595
-
-
(g) Larock, R. C.; Doty, M. J.; Han, X. J. Org. Chem. 1999, 64, 8770.
-
(1999)
J. Org. Chem.
, vol.64
, pp. 8770
-
-
Larock, R.C.1
Doty, M.J.2
Han, X.3
-
62
-
-
0034614049
-
-
The exact opposite process, β-carbon elimination from a strained cyclobutaniminopalladium complex to produce a γ-cyanoalkylpalladium species, has been reported: Nishimura, T.; Uemura, S. J. Am. Chem. Soc. 2000, 122, 12049.
-
(2000)
J. Am. Chem. Soc.
, vol.122
, pp. 12049
-
-
Nishimura, T.1
Uemura, S.2
-
63
-
-
33845281518
-
-
(a) Abelman, M. M.; Oh, T.; Overman, L. E. J. Org. Chem. 1987, 52, 4130.
-
(1987)
J. Org. Chem.
, vol.52
, pp. 4130
-
-
Abelman, M.M.1
Oh, T.2
Overman, L.E.3
-
64
-
-
0001541185
-
-
(b) Karabelas, K.; Westerlund, C.; Hallberg, A. J. Org. Chem. 1985, 50, 3896.
-
(1985)
J. Org. Chem.
, vol.50
, pp. 3896
-
-
Karabelas, K.1
Westerlund, C.2
Hallberg, A.3
-
65
-
-
0001026642
-
-
(c) Cabri, W.; Candiani, I.; Bedeschi, A.; Penco, S.; Santi, R. J. Org. Chem. 1992, 57, 1481.
-
(1992)
J. Org. Chem.
, vol.57
, pp. 1481
-
-
Cabri, W.1
Candiani, I.2
Bedeschi, A.3
Penco, S.4
Santi, R.5
-
66
-
-
0026027267
-
-
(d) Grigg, R.; Loganathan, V.; Santhakumar, V.; Sridharan, V.; Teasdale, A. Tetrahedron Lett. 1991, 32, 687.
-
(1991)
Tetrahedron Lett.
, vol.32
, pp. 687
-
-
Grigg, R.1
Loganathan, V.2
Santhakumar, V.3
Sridharan, V.4
Teasdale, A.5
-
68
-
-
0000470387
-
-
(b) Cacchi, S.; Felici, M.; Pietroni, B. Tetrahedron Lett. 1984, 25, 3137.
-
(1984)
Tetrahedron Lett.
, vol.25
, pp. 3137
-
-
Cacchi, S.1
Felici, M.2
Pietroni, B.3
-
69
-
-
37049095637
-
-
and references therein
-
(a) McCrindle, R.; Ferguson, G.; Arsenault, G. J.; McAlees, A. J. J. Chem. Soc., Chem. Commun. 1983, 571 and references therein.
-
(1983)
J. Chem. Soc., Chem. Commun.
, pp. 571
-
-
McCrindle, R.1
Ferguson, G.2
Arsenault, G.J.3
McAlees, A.J.4
-
70
-
-
0000104822
-
-
(b) Trzeciak, A. M.; Ciunik, Z.; Ziolkowski, J. J. Organometallics 2002, 21, 132.
-
(2002)
Organometallics
, vol.21
, pp. 132
-
-
Trzeciak, A.M.1
Ciunik, Z.2
Ziolkowski, J.J.3
-
71
-
-
0000846446
-
-
(a) Murahashi, S.-I.; Hirano, T.; Yano, T. J. Am. Chem. Soc. 1978, 100, 348.
-
(1978)
J. Am. Chem. Soc.
, vol.100
, pp. 348
-
-
Murahashi, S.-I.1
Hirano, T.2
Yano, T.3
-
74
-
-
0346522055
-
-
note
-
2O and our intermediate C can explain the formation of deuterium-containing products in ref 31b without involving β-C-H bond activation.
-
-
-
-
75
-
-
0346522054
-
-
(a) Amrein, W.; Larsson, I.-M.; Schaffer, K. Helv. Chim. Acta 1974, 57, 2519.
-
(1974)
Helv. Chim. Acta
, vol.57
, pp. 2519
-
-
Amrein, W.1
Larsson, I.-M.2
Schaffer, K.3
-
76
-
-
0032510262
-
-
(b) Brown, D.; Grigg, R.; Sridharan, V.; Tambyraiah, V.; Thornton-Pett, M. Tetrahedron 1998, 54, 2595.
-
(1998)
Tetrahedron
, vol.54
, pp. 2595
-
-
Brown, D.1
Grigg, R.2
Sridharan, V.3
Tambyraiah, V.4
Thornton-Pett, M.5
-
77
-
-
0035833048
-
-
and references therein
-
1H NMR spectroscopic methods of assigning the stereochemistry of bicyclic systems, see: Mayo, P.; Tam, W. Tetrahedron 2001, 57, 5943 and references therein.
-
(2001)
Tetrahedron
, vol.57
, pp. 5943
-
-
Mayo, P.1
Tam, W.2
-
79
-
-
4243565366
-
-
(a) Wertz, D. W.; Moseley, M. A. Spectrochim. Acta, Part A 1980, 36A, 467.
-
(1980)
Spectrochim. Acta, Part A
, vol.36 A
, pp. 467
-
-
Wertz, D.W.1
Moseley, M.A.2
-
81
-
-
0001729405
-
-
Trost, B. M., Ed.; Pergamon Press: New York; Chapter 21
-
Gawley, R. E.; Rein, K. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: New York, 1991; Vol. 1, Chapter 2.1, pp 461 and 468.
-
(1991)
Comprehensive Organic Synthesis
, vol.1
, pp. 461
-
-
Gawley, R.E.1
Rein, K.2
-
83
-
-
0346522051
-
-
Moritani, I.; Toshima, N.; Nakagawa, S.; Yakushiji, M. Bull. Chem. Soc. Jpn. 1967, 40, 2129.
-
(1967)
Bull. Chem. Soc. Jpn.
, vol.40
, pp. 2129
-
-
Moritani, I.1
Toshima, N.2
Nakagawa, S.3
Yakushiji, M.4
-
84
-
-
37049068564
-
-
Cheng, K. F.; Chan, T. T.; Lai, T. F.; Kong, Y. C. J. Chem. Soc., Perkin Trans. 1 1988, 3317.
-
(1988)
J. Chem. Soc., Perkin Trans. 1
, pp. 3317
-
-
Cheng, K.F.1
Chan, T.T.2
Lai, T.F.3
Kong, Y.C.4
-
85
-
-
0346522053
-
-
note
-
This model can also account for the results we have obtained in the attempted annulation of diphenylacetylene by 2-bromobenzonitrile (30% yield of 1 with 80% conversion of the starting material after 72 h) and 2-cyanophenyl triflate (no annulation product). The annulation is probably impeded since the Pd-Br bond in IIIa (X = Br) would reduce the partial negative charge on the vinylic carbon due to bromine's relatively high electronegativity, and palladium triflates (IIIa, X = OTf) are known to easily dissociate and form cationic palladium complexes, obviously incapable of nucleophilic reactions.
-
-
-
-
86
-
-
0002934419
-
-
Ukai, T.; Kawazura, H.; Ishii, Y.; Bonnet, J. J.; Ibers, J. A. J. Organomet. Chem. 1974, 65, 253.
-
(1974)
J. Organomet. Chem.
, vol.65
, pp. 253
-
-
Ukai, T.1
Kawazura, H.2
Ishii, Y.3
Bonnet, J.J.4
Ibers, J.A.5
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