-
2
-
-
84985609802
-
-
For the first report of transition-metal-catalyzed hydroboration see: Manning, D.; Nöth, H. Angew. Chem., Int. Ed. Engl. 1985, 24, 878-879.
-
(1985)
Angew. Chem., Int. Ed. Engl.
, vol.24
, pp. 878-879
-
-
Manning, D.1
Nöth, H.2
-
4
-
-
2042507954
-
-
An excellent review of Pd-catalyzed cross-couplings of boronic acids has recently appeared: Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483.
-
(1995)
Chem. Rev.
, vol.95
, pp. 2457-2483
-
-
Miyaura, N.1
Suzuki, A.2
-
5
-
-
0000441415
-
-
Evans, D. A.; Fu, G. C.; Hoveyda, A. H. J. Am. Chem. Soc. 1992, 114, 6671-6679.
-
(1992)
J. Am. Chem. Soc.
, vol.114
, pp. 6671-6679
-
-
Evans, D.A.1
Fu, G.C.2
Hoveyda, A.H.3
-
6
-
-
0000526264
-
-
Evans, D. A.; Fu, G. C.; Anderson, B. A. J. Am. Chem. Soc. 1992, 114, 6679-6685.
-
(1992)
J. Am. Chem. Soc.
, vol.114
, pp. 6679-6685
-
-
Evans, D.A.1
Fu, G.C.2
Anderson, B.A.3
-
7
-
-
33751500413
-
-
Burgess, K.; van der Donk, W. A.; Kook, A. M. J. Org. Chem. 1991, 56, 2949-2951.
-
(1991)
J. Org. Chem.
, vol.56
, pp. 2949-2951
-
-
Burgess, K.1
Van Der Donk, W.A.2
Kook, A.M.3
-
8
-
-
0000878323
-
-
Burgess, K.; van der Donk, W. A.; Westcott, S. A.; Marder, T. B.; Baker, R. T.; Calabrese, J. C. J. Am. Chem. Soc. 1992, 114, 9350-9359.
-
(1992)
J. Am. Chem. Soc.
, vol.114
, pp. 9350-9359
-
-
Burgess, K.1
Van Der Donk, W.A.2
Westcott, S.A.3
Marder, T.B.4
Baker, R.T.5
Calabrese, J.C.6
-
9
-
-
37049077787
-
-
Westcott, S. A.; Taylor, N. J.; Marder, T. B.; Baker, R. T.; Jones, N. L.; Calabrese, J. C. J. Chem. Soc., Chem. Commun. 1991, 304-305.
-
(1991)
J. Chem. Soc., Chem. Commun.
, pp. 304-305
-
-
Westcott, S.A.1
Taylor, N.J.2
Marder, T.B.3
Baker, R.T.4
Jones, N.L.5
Calabrese, J.C.6
-
10
-
-
0001360533
-
-
Westcott, S. A.; Blom, H. P.; Marder, T. B.; Baker, R. T. J. Am. Chem. Soc. 1992, 114, 8863-8869.
-
(1992)
J. Am. Chem. Soc.
, vol.114
, pp. 8863-8869
-
-
Westcott, S.A.1
Blom, H.P.2
Marder, T.B.3
Baker, R.T.4
-
13
-
-
33748212870
-
-
Erker, G.; Noe, R.; Wingbermuhle, D.; Petersen, J. L. Angew. Chem., Int. Ed. Engl. 1993, 32, 1213-1215.
-
(1993)
Angew. Chem., Int. Ed. Engl.
, vol.32
, pp. 1213-1215
-
-
Erker, G.1
Noe, R.2
Wingbermuhle, D.3
Petersen, J.L.4
-
14
-
-
0000286170
-
-
Deloux, L.; Skrzypczak-Jankun, E.; Cheesman, B. V.; Srebnik, M.; Sabat, M. J. Am. Chem. Soc. 1994, 116, 10302-10303.
-
(1994)
J. Am. Chem. Soc.
, vol.116
, pp. 10302-10303
-
-
Deloux, L.1
Skrzypczak-Jankun, E.2
Cheesman, B.V.3
Srebnik, M.4
Sabat, M.5
-
18
-
-
84957427093
-
-
Moezzi, A.; Olmstead, M. M.; Power, P. P. J. Am. Chem. Soc. 1992, 114, 2715-2717.
-
(1992)
J. Am. Chem. Soc.
, vol.114
, pp. 2715-2717
-
-
Moezzi, A.1
Olmstead, M.M.2
Power, P.P.3
-
19
-
-
37049082775
-
-
Moezzi, A.; Olmstead, M. M.; Power, P. P. J. Chem. Soc., Dalton Trans. 1992, 2429-2434.
-
(1992)
J. Chem. Soc., Dalton Trans.
, pp. 2429-2434
-
-
Moezzi, A.1
Olmstead, M.M.2
Power, P.P.3
-
20
-
-
0000683896
-
-
Nguyen, P.; Lesley, G.; Taylor, N. J.; Marder, T. B.; Pickett, N. L.; Clegg, W.; Elsegood, M. R. J.; Norman, N. C. Inorg. Chem. 1994, 35, 4623-4624.
-
(1994)
Inorg. Chem.
, vol.35
, pp. 4623-4624
-
-
Nguyen, P.1
Lesley, G.2
Taylor, N.J.3
Marder, T.B.4
Pickett, N.L.5
Clegg, W.6
Elsegood, M.R.J.7
Norman, N.C.8
-
22
-
-
0001360393
-
-
Ishiyama, T.; Matsuda, N.; Miyaura, N.; Suzuki, A. J. Am. Chem. Soc. 1993, 115, 11018-11019.
-
(1993)
J. Am. Chem. Soc.
, vol.115
, pp. 11018-11019
-
-
Ishiyama, T.1
Matsuda, N.2
Miyaura, N.3
Suzuki, A.4
-
23
-
-
0000302307
-
-
Ishiyama, T.; Matsuda, N.; Murata, M.; Ozawa, F.; Suzuki, A.; Miyaura, N. Organometallics 1996, 15, 713-720.
-
(1996)
Organometallics
, vol.15
, pp. 713-720
-
-
Ishiyama, T.1
Matsuda, N.2
Murata, M.3
Ozawa, F.4
Suzuki, A.5
Miyaura, N.6
-
24
-
-
33748236879
-
-
Baker, R. T.; Nguyen, P.; Marder, T. B.; Westcott, S. A. Angew. Chem., Int. Ed. Engl. 1995, 34, 1336-7.
-
(1995)
Angew. Chem., Int. Ed. Engl.
, vol.34
, pp. 1336-1337
-
-
Baker, R.T.1
Nguyen, P.2
Marder, T.B.3
Westcott, S.A.4
-
25
-
-
85087582752
-
-
note
-
3 by CatB-BCat was reported.
-
-
-
-
26
-
-
0000126176
-
-
Related B-C bond forming reactions of metal boryls have been reported: Waltz, K. M.; He, X.; Muhoro, C.; Hartwig, J. F. J. Am. Chem. Soc. 1995, 117, 11357-11358.
-
(1995)
J. Am. Chem. Soc.
, vol.117
, pp. 11357-11358
-
-
Waltz, K.M.1
He, X.2
Muhoro, C.3
Hartwig, J.F.4
-
27
-
-
0000056787
-
-
For the first report of alkene insertion into a metal-boron linkage see: Baker, R. T.; Calabrese, J. C.; Westcott, S. A.; Nguyen, P.; Marder, T. B. J. Am. Chem. Soc. 1993, 115, 4367-8.
-
(1993)
J. Am. Chem. Soc.
, vol.115
, pp. 4367-4368
-
-
Baker, R.T.1
Calabrese, J.C.2
Westcott, S.A.3
Nguyen, P.4
Marder, T.B.5
-
30
-
-
33745121502
-
-
Dorigo, A. E.; Schleyer, P. v. R. Angew. Chem., Int. Ed. Engl. 1995, 34, 115-117.
-
(1995)
Angew. Chem., Int. Ed. Engl.
, vol.34
, pp. 115-117
-
-
Dorigo, A.E.1
Schleyer, P.V.R.2
-
31
-
-
0001688220
-
-
30 bonds in the boryl-hydride complex derived from oxidative addition of catecholborane to Wilkinson's catalyst. Alkyne insertion into the Ir-H bond of an iridium hydridoboryl complex: Knorr, J. R.; Merola, J. S. Organometallics 1990, 9, 3008-3009.
-
(1990)
Organometallics
, vol.9
, pp. 3008-3009
-
-
Knorr, J.R.1
Merola, J.S.2
-
32
-
-
0000053356
-
-
Associative pathways for alkyne insertion and alkene exchange have been proposed for Ni(II) and Pd(II) square-planar complexes: Gridnev, I. D.; Miyaura, N.; Suzuki, A. Organometallics 1993, 12, 589-592.
-
(1993)
Organometallics
, vol.12
, pp. 589-592
-
-
Gridnev, I.D.1
Miyaura, N.2
Suzuki, A.3
-
33
-
-
6544241298
-
-
The evidence for associative pathways for alkene exchange is convincing: Johnson, L. K.; Killian, C. M.; Brookhart, M. J. Am. Chem. Soc. 1995, 117, 6414-6415.
-
(1995)
J. Am. Chem. Soc.
, vol.117
, pp. 6414-6415
-
-
Johnson, L.K.1
Killian, C.M.2
Brookhart, M.3
-
35
-
-
0021497508
-
-
Phosphine dissociation in Pd(II) alkyl comlexes precedes alkyne insertion into Pd-C bonds: Samsel, E. G.; Norton, J. R. J. Am. Chem. Soc. 1984, 106, 5505-5512.
-
(1984)
J. Am. Chem. Soc.
, vol.106
, pp. 5505-5512
-
-
Samsel, E.G.1
Norton, J.R.2
-
36
-
-
33847089699
-
-
Calculations predict that barriers for reductive elimination are lower for three-coordinate, 14 electron dialkyl complexes as opposed to square-planar 16 electron species. This has been confirmed experimentally.: Kominya, S.; Albright, T. A.; Hoffmann, R.; Kochi, J. K. J. Am. Chem. Soc. 1977, 99, 8440.
-
(1977)
J. Am. Chem. Soc.
, vol.99
, pp. 8440
-
-
Kominya, S.1
Albright, T.A.2
Hoffmann, R.3
Kochi, J.K.4
-
37
-
-
0012599767
-
-
McDermott, J. X.; White, J. F.; Whitesides, G. M. J. Am. Chem. Soc. 1976, 98, 6521-6536.
-
(1976)
J. Am. Chem. Soc.
, vol.98
, pp. 6521-6536
-
-
McDermott, J.X.1
White, J.F.2
Whitesides, G.M.3
-
40
-
-
5244258232
-
-
note
-
Boryl ligands are isolobal to carbene radical cations.
-
-
-
-
41
-
-
33847085021
-
-
Experimental and theoretical work suggest that reductive elimination from a three-coordinate intermediate, such as 6, is reasonable. However, reductive elimination from square-planar Pt(II) complexes has been observed: Sen, A.; Halpern, J. Inorg. Chem. 1980, 19, 1073-1075.
-
(1980)
Inorg. Chem.
, vol.19
, pp. 1073-1075
-
-
Sen, A.1
Halpern, J.2
-
42
-
-
5244277498
-
-
note
-
4-Octyne was diborylated under catalytic conditions. Once the reaction was complete, 3-hexyne was added to the reaction mixture and the solution was heated for 5 h at 80 °C. Diborylation of hexyne was not observed.
-
-
-
-
44
-
-
5244253398
-
-
note
-
See the Experimental Section for details regarding rate law derivation.
-
-
-
-
45
-
-
0000549036
-
-
McCarthy, T. J.; Nuzzo, R. G.; Whitesides, G. M. J. Am. Chem. Soc. 1981, 103, 3396.
-
(1981)
J. Am. Chem. Soc.
, vol.103
, pp. 3396
-
-
McCarthy, T.J.1
Nuzzo, R.G.2
Whitesides, G.M.3
-
46
-
-
5244301999
-
-
Wilkins, R. G., Ed.; VCH: Weiheim, Germany
-
Wilkins, R. G. Kinetics and Mechanisms of Transition Metal Complexes; Wilkins, R. G., Ed.; VCH: Weiheim, Germany, 1991, p 109.
-
(1991)
Kinetics and Mechanisms of Transition Metal Complexes
, pp. 109
-
-
Wilkins, R.G.1
-
47
-
-
0000215451
-
-
Burger, B. J.; Santarsiero, B. D.; Trimmer, M. S.; Bercaw, J. E. J. Am. Chem. Soc. 1988, 110, 3134-3146.
-
(1988)
J. Am. Chem. Soc.
, vol.110
, pp. 3134-3146
-
-
Burger, B.J.1
Santarsiero, B.D.2
Trimmer, M.S.3
Bercaw, J.E.4
-
48
-
-
85087580018
-
-
note
-
2Pt" fragment.
-
-
-
-
49
-
-
5244341084
-
-
note
-
In all kinetic runs, the NMR tubes were heated briefly at 50 °C to dissolve the substrate. The integrity of the sample was confirmed by NMR prior to kinetic runs at 70 °C. In the case of 1,2-bis[p-(trifluoromethyl)phenyl]acetylene, approximately 50% of the alkyne was diborylated during dissolution at 50 °C.
-
-
-
-
50
-
-
0003887404
-
-
Lowry, T. H., Richardson, K. S., Eds.; Harper and Row: New York
-
Lowry, T. H.; Richardson, K. S. Mechanism and Theory in Organic Chemistry, 2nd ed.; Lowry, T. H., Richardson, K. S., Eds.; Harper and Row: New York, 1981; p 131.
-
(1981)
Mechanism and Theory in Organic Chemistry, 2nd Ed.
, pp. 131
-
-
Lowry, T.H.1
Richardson, K.S.2
-
51
-
-
85087581714
-
-
note
-
1H} NMR spectra, which corresponded to the reported literature values.
-
-
-
-
52
-
-
0001096291
-
-
The B-B bond in PinB-BPin measures 1.711(6) Å and is significantly longer than the B-B bond in related catecholate deriva-tives where the B-B distances are 1.68 Å: Nöth, H. Z. Naturforsch. 1984, 39b, 1463-1466.
-
(1984)
Z. Naturforsch.
, vol.39 B
, pp. 1463-1466
-
-
Nöth, H.1
-
53
-
-
1542508234
-
-
Alkyne complexes in these systems are known to react via associative and dissociative pathways: Birk, J. P.; Halpern, J.; Pickard, A. L. Inorg. Chem. 1968, 7, 2672-2673.
-
(1968)
Inorg. Chem.
, vol.7
, pp. 2672-2673
-
-
Birk, J.P.1
Halpern, J.2
Pickard, A.L.3
-
56
-
-
34248223464
-
-
Camalli, M.; Caruso, F.; Chaloupka, S.; Leber, E. M.; Rimml, H.; Venanzi, L. M. Helv. Chim. Acta 1990, 73, 2263-2274.
-
(1990)
Helv. Chim. Acta
, vol.73
, pp. 2263-2274
-
-
Camalli, M.1
Caruso, F.2
Chaloupka, S.3
Leber, E.M.4
Rimml, H.5
Venanzi, L.M.6
-
60
-
-
33845469499
-
-
For olefinic protons: (a) Engman, L. J. Org. Chem. 1984, 49, 3559-3563.
-
(1984)
J. Org. Chem.
, vol.49
, pp. 3559-3563
-
-
Engman, L.1
-
62
-
-
0001739401
-
-
Bellucci, G.; Bianchini, R.; Chiappe, C.; Brown, R. S.; Sleboka-Tilk, H. J. Am. Chem. Soc. 1991, 113, 8012-8016.
-
(1991)
J. Am. Chem. Soc.
, vol.113
, pp. 8012-8016
-
-
Bellucci, G.1
Bianchini, R.2
Chiappe, C.3
Brown, R.S.4
Sleboka-Tilk, H.5
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