-
1
-
-
0036589259
-
-
J. Hassan, M. Sévignon, C. Gozzi, E. Sculz, M. Lemaire, Chem. Rev. 2002, 102, 1359.
-
(2002)
Chem. Rev.
, vol.102
, pp. 1359
-
-
Hassan, J.1
Sévignon, M.2
Gozzi, C.3
Sculz, E.4
Lemaire, M.5
-
2
-
-
0000658001
-
-
For the palladium-catalyzed dimerization of aryl halides, see: a) D. D. Hennings, T. Iwama, V. H. Rawal, Org. Lett. 1999, 1, 1205; b) J. Hassan, V. Penalva, L. Lavenot, C. Gozzi, M. Lemaire, Tetrahedron 1998, 54, 13793; c) F.-T. Luo, A. Jeevanandam, M. K. Basu, Tetrahedron Lett. 1998, 39, 7939.
-
(1999)
Org. Lett.
, vol.1
, pp. 1205
-
-
Hennings, D.D.1
Iwama, T.2
Rawal, V.H.3
-
3
-
-
0032487938
-
-
For the palladium-catalyzed dimerization of aryl halides, see: a) D. D. Hennings, T. Iwama, V. H. Rawal, Org. Lett. 1999, 1, 1205; b) J. Hassan, V. Penalva, L. Lavenot, C. Gozzi, M. Lemaire, Tetrahedron 1998, 54, 13793; c) F.-T. Luo, A. Jeevanandam, M. K. Basu, Tetrahedron Lett. 1998, 39, 7939.
-
(1998)
Tetrahedron
, vol.54
, pp. 13793
-
-
Hassan, J.1
Penalva, V.2
Lavenot, L.3
Gozzi, C.4
Lemaire, M.5
-
4
-
-
0032558674
-
-
For the palladium-catalyzed dimerization of aryl halides, see: a) D. D. Hennings, T. Iwama, V. H. Rawal, Org. Lett. 1999, 1, 1205; b) J. Hassan, V. Penalva, L. Lavenot, C. Gozzi, M. Lemaire, Tetrahedron 1998, 54, 13793; c) F.-T. Luo, A. Jeevanandam, M. K. Basu, Tetrahedron Lett. 1998, 39, 7939.
-
(1998)
Tetrahedron Lett.
, vol.39
, pp. 7939
-
-
Luo, F.-T.1
Jeevanandam, A.2
Basu, M.K.3
-
5
-
-
17044438702
-
-
Ed.: F. Diederich, P. J. Stang, Wiley-VCH, New York, chap. 4
-
For palladium-catalyzed cross-coupling reactions, see: a) T. N. Mitchell in Metal-Catalyzed Cross-Coupling Reactions (Ed.: F. Diederich, P. J. Stang), Wiley-VCH, New York, 1998, chap. 4; b) N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457; c) E. Negishi, Acc. Chem. Res. 1982, 15, 340.
-
(1998)
Metal-Catalyzed Cross-Coupling Reactions
-
-
Mitchell, T.N.1
-
6
-
-
2042507954
-
-
For palladium-catalyzed cross-coupling reactions, see: a) T. N. Mitchell in Metal-Catalyzed Cross-Coupling Reactions (Ed.: F. Diederich, P. J. Stang), Wiley-VCH, New York, 1998, chap. 4; b) N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457; c) E. Negishi, Acc. Chem. Res. 1982, 15, 340.
-
(1995)
Chem. Rev.
, vol.95
, pp. 2457
-
-
Miyaura, N.1
Suzuki, A.2
-
7
-
-
33750026643
-
-
For palladium-catalyzed cross-coupling reactions, see: a) T. N. Mitchell in Metal-Catalyzed Cross-Coupling Reactions (Ed.: F. Diederich, P. J. Stang), Wiley-VCH, New York, 1998, chap. 4; b) N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457; c) E. Negishi, Acc. Chem. Res. 1982, 15, 340.
-
(1982)
Acc. Chem. Res.
, vol.15
, pp. 340
-
-
Negishi, E.1
-
8
-
-
0034817381
-
-
a) R. Hong, R. Hoen, J. Zhang, G. Lin, Synlett 2001, 1527;
-
(2001)
Synlett
, pp. 1527
-
-
Hong, R.1
Hoen, R.2
Zhang, J.3
Lin, G.4
-
9
-
-
33845557330
-
-
b) M. F. Semmelhack, P. Helquist, L. D. Jones, L. Keller, L. Mendelson, L. S. Ryono, J. G. Smith, R. D. Stauffer, J. Am. Chem. Soc. 1981, 103, 6461.
-
(1981)
J. Am. Chem. Soc.
, vol.103
, pp. 6461
-
-
Semmelhack, M.F.1
Helquist, P.2
Jones, L.D.3
Keller, L.4
Mendelson, L.5
Ryono, L.S.6
Smith, J.G.7
Stauffer, R.D.8
-
11
-
-
1942436903
-
-
for a recent application, see: b) A. I. Meyers, T. D. Nelson, H. Moorlag, D. J. Rawson, A. Meier, Tetrahedron 2004, 60, 4459.
-
(2004)
Tetrahedron
, vol.60
, pp. 4459
-
-
Meyers, A.I.1
Nelson, T.D.2
Moorlag, H.3
Rawson, D.J.4
Meier, A.5
-
12
-
-
0141658841
-
-
a) Oxidative coupling, for example: B. Kramer, A. Averhoff, S. R. Waldvogel, Angew. Chem. 2002, 114, 3103; Angew. Chem. Int. Ed. 2002, 41, 2981;
-
(2002)
Angew. Chem.
, vol.114
, pp. 3103
-
-
Kramer, B.1
Averhoff, A.2
Waldvogel, S.R.3
-
13
-
-
0037118887
-
-
a) Oxidative coupling, for example: B. Kramer, A. Averhoff, S. R. Waldvogel, Angew. Chem. 2002, 114, 3103; Angew. Chem. Int. Ed. 2002, 41, 2981;
-
(2002)
Angew. Chem. Int. Ed.
, vol.41
, pp. 2981
-
-
-
14
-
-
0000139143
-
-
b) Ullmann-type coupling, for example: S. Zhang, D. Zhang, L. S. Liebeskind, J. Org. Chem. 1997, 62, 2312;
-
(1997)
J. Org. Chem.
, vol.62
, pp. 2312
-
-
Zhang, S.1
Zhang, D.2
Liebeskind, L.S.3
-
15
-
-
85046521144
-
-
c) radical coupling: H. Tanaka, M. Doi, H. Shimizu, H. Etoh, Heterocycles 1999, 51, 2415;
-
(1999)
Heterocycles
, vol.51
, pp. 2415
-
-
Tanaka, H.1
Doi, M.2
Shimizu, H.3
Etoh, H.4
-
16
-
-
0006949404
-
-
d) reductive coupling: S. Miyake, A. Sasaki, T. Ohta, K. Shudo, Tetrahedron Lett. 1985, 26, 5815.
-
(1985)
Tetrahedron Lett.
, vol.26
, pp. 5815
-
-
Miyake, S.1
Sasaki, A.2
Ohta, T.3
Shudo, K.4
-
18
-
-
11444254369
-
-
a) W. Su, S. Urgaonkar, P. M. McLaughlin, J. G. Verkade, J. Am. Chem. Soc. 2004, 126, 16433;
-
(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 16433
-
-
Su, W.1
Urgaonkar, S.2
McLaughlin, P.M.3
Verkade, J.G.4
-
19
-
-
9344240844
-
-
b) G. Altenhoff, R. Goddard, C. W. Lehmann, F. Glorius, J. Am. Chem. Soc. 2004, 126, 15195;
-
(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 15195
-
-
Altenhoff, G.1
Goddard, R.2
Lehmann, C.W.3
Glorius, F.4
-
23
-
-
0034742965
-
-
a) Direct iodination: P. C. Anelli, M. Brochetta, C. Maffezzoni, P. Paoli, P. Rossi, F. Uggeri, M. Visigalli, Perkin Trans, 1 2001, 1175;
-
(2001)
Perkin Trans, 1
, pp. 1175
-
-
Anelli, P.C.1
Brochetta, M.2
Maffezzoni, C.3
Paoli, P.4
Rossi, P.5
Uggeri, F.6
Visigalli, M.7
-
25
-
-
0000600868
-
-
c) from an aryne: H. Hart, K. Harada, C.-J. F. Du, J. Org. Chem. 1985, 50, 3104;
-
(1985)
J. Org. Chem.
, vol.50
, pp. 3104
-
-
Hart, H.1
Harada, K.2
Du, C.-J.F.3
-
26
-
-
3042839782
-
-
and references therein
-
d) oxidative coupling: D. Mirk, A. Willner, R. Frölich, S. R. Waldvogel, Adv. Synth. Catal. 2004, 346, 675, and references therein.
-
(2004)
Adv. Synth. Catal.
, vol.346
, pp. 675
-
-
Mirk, D.1
Willner, A.2
Frölich, R.3
Waldvogel, S.R.4
-
27
-
-
33947337524
-
-
a) For the first detailed studies, see: G. M. Whitesides, J. SanFilippo, Jr., C. P. Casey, E. P. Panek, J. Am. Chem. Soc. 1967, 89, 5302;
-
(1967)
J. Am. Chem. Soc.
, vol.89
, pp. 5302
-
-
Whitesides, G.M.1
Sanfilippo Jr., J.2
Casey, C.P.3
Panek, E.P.4
-
29
-
-
0346471289
-
-
and references therein
-
c) for the oxidation of organocuprates under "kinetic" conditions, see: B. H. Lipshutz, K. Siegmann, E. Garcia, F. Kayser, J. Am. Chem. Soc. 1993, 115, 9276, and references therein;
-
(1993)
J. Am. Chem. Soc.
, vol.115
, pp. 9276
-
-
Lipshutz, B.H.1
Siegmann, K.2
Garcia, E.3
Kayser, F.4
-
30
-
-
0037039030
-
-
e) for a recent application in crystal engineering, see: Y. Morita, T. Murata, S. Yamada, M. Tadokoro, A. Ichimura, K. Nakasuji, J. Chem. Soc. Perkin Trans, 1 2002, 2598.
-
(2002)
J. Chem. Soc. Perkin Trans, 1
, pp. 2598
-
-
Morita, Y.1
Murata, T.2
Yamada, S.3
Tadokoro, M.4
Ichimura, A.5
Nakasuji, K.6
-
31
-
-
0001206442
-
-
a) B. H. Lipshutz, F. Kayser, Z.-P. Liu, Angew. Chem. 1994, 106, 1962; Angew. Chem. Int. Ed. Engl. 1994, 33, 1844;
-
(1994)
Angew. Chem.
, vol.106
, pp. 1962
-
-
Lipshutz, B.H.1
Kayser, F.2
Liu, Z.-P.3
-
32
-
-
33748214746
-
-
a) B. H. Lipshutz, F. Kayser, Z.-P. Liu, Angew. Chem. 1994, 106, 1962; Angew. Chem. Int. Ed. Engl. 1994, 33, 1844;
-
(1994)
Angew. Chem. Int. Ed. Engl.
, vol.33
, pp. 1844
-
-
-
33
-
-
0037138650
-
-
b) D. R. Spring, S. Krishnan, H. E. Blackwell, S. L. Schreiber, J. Am. Chem. Soc. 2002, 124, 1354;
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 1354
-
-
Spring, D.R.1
Krishnan, S.2
Blackwell, H.E.3
Schreiber, S.L.4
-
34
-
-
0031579463
-
-
c) T. Sugimura, H. Yamada, S. Inoue, A. Tai, Tetrahedron: Asymmetry 1997, 8, 649;
-
(1997)
Tetrahedron: Asymmetry
, vol.8
, pp. 649
-
-
Sugimura, T.1
Yamada, H.2
Inoue, S.3
Tai, A.4
-
35
-
-
0032543504
-
-
d) A.-C. Carbonnelle, E. G. Zamora, R. Beugelmans, G. Roussi, Tetrahedron Lett. 1998, 39, 4471;
-
(1998)
Tetrahedron Lett.
, vol.39
, pp. 4471
-
-
Carbonnelle, A.-C.1
Zamora, E.G.2
Beugelmans, R.3
Roussi, G.4
-
37
-
-
0036201102
-
-
and references therein
-
A. E. Jensen, W. Dohle, I. Sapountzis, D. M. Lindsay, V. A. Vu, P. Knochel, Synthesis 2002, 565, and references therein.
-
(2002)
Synthesis
, pp. 565
-
-
Jensen, A.E.1
Dohle, W.2
Sapountzis, I.3
Lindsay, D.M.4
Vu, V.A.5
Knochel, P.6
-
38
-
-
17044373648
-
-
note
-
CuCN, CuSCN, and CuI gave comparable but lower yields.
-
-
-
-
40
-
-
17044408033
-
-
note
-
4, 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ), and potassium nitrosodisulfonate (Fremy's salt), gave unsatisfactory yields.
-
-
-
-
41
-
-
17044439160
-
-
note
-
This compound is readily synthesized in high yield on a large scale from commercially available starting materials (see the Supporting Information) and can be stored indefinitely at room temperature.
-
-
-
-
42
-
-
17044409738
-
-
The dianion of dinitrobenzene has been studied electrochemically; for an example see: H. Wang, V. D. Parker, Acta Chem. Scand. 1994, 48, 933.
-
(1994)
Acta Chem. Scand.
, vol.48
, pp. 933
-
-
Wang, H.1
Parker, V.D.2
-
43
-
-
17044391900
-
-
note
-
An alternative possibility is that the biphenyl product can itself act as a single-electron oxidant; however, this possibility was ruled out as biphenyl did not act as an oxidant in control reactions.
-
-
-
-
44
-
-
4644300966
-
-
It has recently been found that this dimerization proceeds in only moderate yield in a palladium-catalyzed system, see: C. F. Nising, U. K. Schmid, M. Nieger, S. Bräse, J. Org. Chem. 2004, 69, 6830.
-
(2004)
J. Org. Chem.
, vol.69
, pp. 6830
-
-
Nising, C.F.1
Schmid, U.K.2
Nieger, M.3
Bräse, S.4
-
45
-
-
14744285625
-
-
The halogen-metal exchange has recently been extended to allow the formation of aryl magnesium compounds from the corresponding aryl bromides: A. Krasovskiy, P. Knochel, Angew. Chem. 2004, 116, 3396; Angew. Chem. Int. Ed. 2004, 43, 3333. Our preliminary investigations suggest that Grignard reagents formed in this way may also be used to form organocuprates, which may be successfully oxidized under our conditions.
-
(2004)
Angew. Chem.
, vol.116
, pp. 3396
-
-
Krasovskiy, A.1
Knochel, P.2
-
46
-
-
4544311534
-
-
The halogen-metal exchange has recently been extended to allow the formation of aryl magnesium compounds from the corresponding aryl bromides: A. Krasovskiy, P. Knochel, Angew. Chem. 2004, 116, 3396; Angew. Chem. Int. Ed. 2004, 43, 3333. Our preliminary investigations suggest that Grignard reagents formed in this way may also be used to form organocuprates, which may be successfully oxidized under our conditions.
-
(2004)
Angew. Chem. Int. Ed.
, vol.43
, pp. 3333
-
-
-
47
-
-
37049068125
-
-
a) M. Takahashi, T. Ogiku, K. Okamura, T. Da-te, H. Ohmizu, K. Kondo, T. Iwasaki, J. Chem. Soc. Perkin Trans, 1 1993, 1473;
-
(1993)
J. Chem. Soc. Perkin Trans, 1
, pp. 1473
-
-
Takahashi, M.1
Ogiku, T.2
Okamura, K.3
Da-te, T.4
Ohmizu, H.5
Kondo, K.6
Iwasaki, T.7
-
48
-
-
0001114197
-
-
b) M. Takahashi, T. Kuroda, T. Ogiku, H. Ohmizu, K. Kondo, T. Iwasaki, Heterocycles 1993, 36, 1867;
-
(1993)
Heterocycles
, vol.36
, pp. 1867
-
-
Takahashi, M.1
Kuroda, T.2
Ogiku, T.3
Ohmizu, H.4
Kondo, K.5
Iwasaki, T.6
-
49
-
-
17044402216
-
-
c) M. Takahashi, T. Kuroda, T. Ogiku, H. Ohmizu, K. Kondo, T. Iwasaki, Heterocycles 1992, 34, 2061;
-
(1992)
Heterocycles
, vol.34
, pp. 2061
-
-
Takahashi, M.1
Kuroda, T.2
Ogiku, T.3
Ohmizu, H.4
Kondo, K.5
Iwasaki, T.6
-
50
-
-
0026037195
-
-
d) M. Takahashi, T. Kuroda, T. Ogiku, H. Ohmizu, K. Kondo, T. Iwasaki, Tetrahedron Lett. 1991, 32, 6919.
-
(1991)
Tetrahedron Lett.
, vol.32
, pp. 6919
-
-
Takahashi, M.1
Kuroda, T.2
Ogiku, T.3
Ohmizu, H.4
Kondo, K.5
Iwasaki, T.6
-
51
-
-
0035966221
-
-
The axial configuration of 2m was assigned by comparison to literature data: G. Capozzi, C. Ciampi, G. Delogu, S. Menichetti, C. Nativi, J. Org. Chem. 2001, 66, 8787.
-
(2001)
J. Org. Chem.
, vol.66
, pp. 8787
-
-
Capozzi, G.1
Ciampi, C.2
Delogu, G.3
Menichetti, S.4
Nativi, C.5
-
52
-
-
0346265937
-
-
Ed.: E. W. Abel, F. G. A. Stone, G. Wilkinson, J. L. Wardell, Pergamon, Oxford, chap. 2
-
G. van Koten, S. L. James, J. T. B. H. Jastrzebski in Comprehensive Organometallic Chemistry 11 (Ed.: E. W. Abel, F. G. A. Stone, G. Wilkinson, J. L. Wardell), Pergamon, Oxford, 1995, chap. 2.
-
(1995)
Comprehensive Organometallic Chemistry
, vol.11
-
-
Van Koten, G.1
James, S.L.2
Jastrzebski, J.T.B.H.3
|