-
2
-
-
0001786881
-
-
Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: Weinheim
-
(b) Suzuki, A. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998; pp. 49-97.
-
(1998)
Metal-Catalyzed Cross-Coupling Reactions
, pp. 49-97
-
-
Suzuki, A.1
-
5
-
-
0000564666
-
-
Smith K.A., Campi E.M., Jackson W.R., Marcuccio S., Naeslund C.G.M., Deacon G.B. Synlett. 1997;131.
-
(1997)
Synlett
, pp. 131
-
-
Smith, K.A.1
Campi, E.M.2
Jackson, W.R.3
Marcuccio, S.4
Naeslund, C.G.M.5
Deacon, G.B.6
-
15
-
-
0035843313
-
-
(d) Savarin, C.; Srogl, J.; Liebeskind, L. S. Org. Lett. 2001, 3, 91;
-
(2001)
Org. Lett.
, vol.3
, pp. 91
-
-
Savarin, C.1
Srogl, J.2
Liebeskind, L.S.3
-
19
-
-
0036158526
-
-
(h) Kakino, R.; Yasumi, S.; Shimizu, I.; Yamamoto, A. Bull. Chem. Soc. Jpn. 2002, 75, 137;
-
(2002)
Bull. Chem. Soc. Jpn.
, vol.75
, pp. 137
-
-
Kakino, R.1
Yasumi, S.2
Shimizu, I.3
Yamamoto, A.4
-
20
-
-
0036300174
-
-
(i) Kakino, R.; Narahashi, H.; Shimizu, I.; Yamamoto, A. Bull. Chem. Soc. Jpn. 2002, 75, 1333.
-
(2002)
Bull. Chem. Soc. Jpn.
, vol.75
, pp. 1333
-
-
Kakino, R.1
Narahashi, H.2
Shimizu, I.3
Yamamoto, A.4
-
21
-
-
5244346814
-
-
Recently, transition metal-catalyzed addition of organoboron compounds to unsaturated organic compounds without added base has attracted considerable attention, see: (a) Sakai, M.; Hayashi, H.; Miyaura, N. Organometallics 1997, 16, 4229;
-
(1997)
Organometallics
, vol.16
, pp. 4229
-
-
Sakai, M.1
Hayashi, H.2
Miyaura, N.3
-
22
-
-
0032542313
-
-
(b) Sakai, M.; Ueda, M.; Miyaura, N. Angew. Chem. Int. Ed. 1998, 37, 3279;
-
(1998)
Angew. Chem. Int. Ed.
, vol.37
, pp. 3279
-
-
Sakai, M.1
Ueda, M.2
Miyaura, N.3
-
23
-
-
0032503611
-
-
(c) Takaya, Y.; Ogasawara, M.; Hayashi, T.; Sakai, M.; Miyaura, N. J. Am. Chem. Soc. 1998, 120, 5579;
-
(1998)
J. Am. Chem. Soc.
, vol.120
, pp. 5579
-
-
Takaya, Y.1
Ogasawara, M.2
Hayashi, T.3
Sakai, M.4
Miyaura, N.5
-
24
-
-
0033572920
-
-
(d) Hayashi, T.; Senda, T.; Takaya, Y.; Ogasawara, M. J. Am. Chem. Soc. 1999, 121, 11591;
-
(1999)
J. Am. Chem. Soc.
, vol.121
, pp. 11591
-
-
Hayashi, T.1
Senda, T.2
Takaya, Y.3
Ogasawara, M.4
-
25
-
-
0034327157
-
-
(e) Hayashi, T.; Senda, T.; Ogasawara, M. J. Am. Chem. Soc. 2000, 122, 10716;
-
(2000)
J. Am. Chem. Soc.
, vol.122
, pp. 10716
-
-
Hayashi, T.1
Senda, T.2
Ogasawara, M.3
-
26
-
-
0035840942
-
-
(f) Hayashi, T.; Inoue, K.; Taniguchi, N.; Ogasawara, M. J. Am. Chem. Soc. 2001, 123, 9918;
-
(2001)
J. Am. Chem. Soc.
, vol.123
, pp. 9918
-
-
Hayashi, T.1
Inoue, K.2
Taniguchi, N.3
Ogasawara, M.4
-
27
-
-
0035930756
-
-
(g) Shirakawa, E.; Takahashi, G.; Tsuchimoto, T.; Kawakami, Y. Chem. Commun. 2001, 2688.
-
(2001)
Chem. Commun.
, pp. 2688
-
-
Shirakawa, E.1
Takahashi, G.2
Tsuchimoto, T.3
Kawakami, Y.4
-
28
-
-
0742313889
-
-
There has been only one report on the palladium-catalyzed base-free oxidative homocoupling of organoboronic acids, however, the low to moderate product yields and the formation of undesirable side-products seem to impair its synthetic utility, see: Moreno-Mañas, M.; Pérez, M.; Pleixats, R. J. Org. Chem. 1996, 61, 2346.
-
(1996)
J. Org. Chem.
, vol.61
, pp. 2346
-
-
Moreno-Mañas, M.1
Pérez, M.2
Pleixats, R.3
-
29
-
-
0001403744
-
-
Although the reaction of organoboranes with oxygen was reported to give the corresponding alcohols, no trace of p-cresol (4) was detected in the reaction of 3 without using the catalyst. This result would rule out the direct oxidation pathway with oxygen in the formation of 4. For the oxidation of trialkylboranes with oxygen, see: Brown, H. C.; Midland, M. M.; Kabalka, G. W. J. Am. Chem. Soc. 1971, 93, 1024.
-
(1971)
J. Am. Chem. Soc.
, vol.93
, pp. 1024
-
-
Brown, H.C.1
Midland, M.M.2
Kabalka, G.W.3
-
35
-
-
0013032936
-
-
Although the ultimate fate of 10 was not identified at present, boron peroxide should decompose into boronic acid, its esters, etc. For thermal decomposition of organoboron peroxides, see: Maslennikov, V. P.; Makin, G. I.; Alyasov, V. N.; Aleksandrov, Y. A. Zh. Obshch. Khim. 1973, 43, 1972.
-
(1973)
Zh. Obshch. Khim.
, vol.43
, pp. 1972
-
-
Maslennikov, V.P.1
Makin, G.I.2
Alyasov, V.N.3
Aleksandrov, Y.A.4
-
36
-
-
0003441482
-
-
Wiley: Chichester; Chap. 3
-
In general, in situ reoxidation of a palladium(0) complex to a palladium(II) complex with molecular oxygen alone is not an easy process, however, DMSO has been reported to be an exceptionally efficient solvent for this purpose: (a) Tsuji, J. Palladium Reagents and Catalysts; Wiley: Chichester, 1995; Chap. 3;
-
(1995)
Palladium Reagents and Catalysts
-
-
Tsuji, J.1
-
38
-
-
37049077422
-
-
(c) van Benthem, R. A. T. M.; Hiemstra, H.; Michels, J. J.; Speckamp, W. N. J. Chem. Soc., Chem. Commun. 1994, 357;
-
(1994)
J. Chem. Soc., Chem. Commun.
, pp. 357
-
-
Van Benthem, R.A.T.M.1
Hiemstra, H.2
Michels, J.J.3
Speckamp, W.N.4
-
39
-
-
33748242802
-
-
(d) van Benthem, R. A. T. M.; Hiemstra, H.; van Leeuwen, P. W. N. M.; Geus, J. W.; Speckamp, W. N. Angew. Chem. Int. Ed. Engl. 1995, 34, 457;
-
(1995)
Angew. Chem. Int. Ed. Engl.
, vol.34
, pp. 457
-
-
Van Benthem, R.A.T.M.1
Hiemstra, H.2
Van Leeuwen, P.W.N.M.3
Geus, J.W.4
Speckamp, W.N.5
-
40
-
-
0028899917
-
-
(e) Larock, R. C.; Hightower, T. R.; Kraus, G. A.; Hahn, P.; Zheng, D. Tetrahedron Lett. 1995, 36, 2423;
-
(1995)
Tetrahedron Lett.
, vol.36
, pp. 2423
-
-
Larock, R.C.1
Hightower, T.R.2
Kraus, G.A.3
Hahn, P.4
Zheng, D.5
-
41
-
-
0028832448
-
-
(f) Rönn, M.; Bäckvall, J. E.; Andersson, P. G. Tetrahedron Lett. 1995, 36, 7749.
-
(1995)
Tetrahedron Lett.
, vol.36
, pp. 7749
-
-
Rönn, M.1
Bäckvall, J.E.2
Andersson, P.G.3
-
43
-
-
3142514770
-
-
see also Refs 3a,h,i
-
Ishiyama T., Murata M., Miyaura N. J. Org. Chem. 60:1995;7508. see also Refs 3a,h,i.
-
(1995)
J. Org. Chem.
, vol.60
, pp. 7508
-
-
Ishiyama, T.1
Murata, M.2
Miyaura, N.3
-
44
-
-
0012985333
-
-
note
-
Since addition of 10 mol% of galvinoxyl (a radical scavenger) to the homocoupling of 1b did not affect both the reaction rate and the yield of 2b, we can eliminate the possibility that the present homocoupling proceeds through oxygen-mediated radical pathways. For the radical-chain process observed in the reaction of trialkylboranes with oxygen, see Ref. 6.
-
-
-
-
45
-
-
0000975959
-
-
Liebeskind, L. S., Ed.; JAI Press: London
-
Palladium-catalyzed homocoupling of organoboron compounds using a base and oxygen have also been considered to proceed through palladium(II) peroxide, see: (a) Miyaura, N. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press: London, 1998; Vol. 6, pp. 187-243;
-
(1998)
Advances in Metal-Organic Chemistry
, vol.6
, pp. 187-243
-
-
Miyaura, N.1
|