-
6
-
-
0000314559
-
-
Ed, L. Paquette, John Wiley & Sons, New York
-
c) G. Cahiez, in Encyclopedia of Reagents for Organic Synthesis (Ed.: L. Paquette), John Wiley & Sons, New York, 1995, pp. 925-928.
-
(1995)
Encyclopedia of Reagents for Organic Synthesis
, pp. 925-928
-
-
Cahiez, G.1
-
7
-
-
33845278851
-
-
S. Araki, H. Ito, Y. Butsugan, J. Org. Chem. 1988, 53, 1831-1833.
-
(1988)
J. Org. Chem
, vol.53
, pp. 1831-1833
-
-
Araki, S.1
Ito, H.2
Butsugan, Y.3
-
8
-
-
56049119352
-
-
Manganese powder (325 mesh, >99%) may be purchased from Sigma-Aldrich for approximately $5/mol. For comparison, magnesium turnings (>99.5%) and indium powder (99.999%) may be purchased for $2 per mol and $560 per mol, respectively.
-
Manganese powder (325 mesh, >99%) may be purchased from Sigma-Aldrich for approximately $5/mol. For comparison, magnesium turnings (>99.5%) and indium powder (99.999%) may be purchased for $2 per mol and $560 per mol, respectively.
-
-
-
-
9
-
-
84891011604
-
-
Ed, P. Knochel, Wiley-VCH Verlag, Weinheim
-
G. Cahiez, F. Mahuteau-Betzer, in Handbook of Functionalized, Organometallics Applications to Synthesis (Ed.: P. Knochel), Wiley-VCH Verlag, Weinheim, 2005, vol. 2, pp. 541-567.
-
(2005)
Handbook of Functionalized, Organometallics Applications to Synthesis
, vol.2
, pp. 541-567
-
-
Cahiez, G.1
Mahuteau-Betzer, F.2
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11
-
-
0000296334
-
-
b) M. Alami, S. Marquais, G. Cahiez, Org. Synth. 1995, 72, 135-146.
-
(1995)
Org. Synth
, vol.72
, pp. 135-146
-
-
Alami, M.1
Marquais, S.2
Cahiez, G.3
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12
-
-
0029880915
-
-
S. H. Kim, M. V. Hanson, R. D. Rieke, Tetrahedron Lett. 1996, 37, 2197-2200.
-
(1996)
Tetrahedron Lett
, vol.37
, pp. 2197-2200
-
-
Kim, S.H.1
Hanson, M.V.2
Rieke, R.D.3
-
13
-
-
0030599259
-
-
0 in situ; a K/C: A. Fürstner, H. Brunner, Tetrahedron Lett. 1996, 37, 7009-7012;
-
0 in situ; a) K/C: A. Fürstner, H. Brunner, Tetrahedron Lett. 1996, 37, 7009-7012;
-
-
-
-
14
-
-
0001461066
-
-
LiAlH4
-
4: T. Hiyama, M. Obayashi, A. Nakamura, Organometallics 1982, 1, 1249-1251;
-
(1982)
Organometallics
, vol.1
, pp. 1249-1251
-
-
Hiyama, T.1
Obayashi, M.2
Nakamura, A.3
-
15
-
-
0030599234
-
-
c) TMSCl: K. Takai, T. Ueda, T. Hayashi, T. Moriwake, Tetrahedron Lett. 1996, 37, 7049-7052;
-
(1996)
Tetrahedron Lett
, vol.37
, pp. 7049-7052
-
-
TMSCl, K.1
Takai, T.2
Ueda, T.3
Hayashi, T.M.4
-
16
-
-
56049122656
-
-
TMSCl and indium powder: J. Augé, N. Lubin-Germain, A. Thiaw-Woaye, Tetrahedron Lett. 1996, 40, 9245-9247.
-
d) TMSCl and indium powder: J. Augé, N. Lubin-Germain, A. Thiaw-Woaye, Tetrahedron Lett. 1996, 40, 9245-9247.
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-
-
-
17
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-
56049106579
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-
Chlorosilanes are also key reagents in manganese-mediated, chromium- and nickel-catalyzed Nozaki-Hiyama-Kishi (NHK) allylation reactions, wherein chlorosilane is proposed to facilitate turnover of the resultant chromium alkoxide; a) For a discussion of the mechanism of manganese-mediated NHK reaction, see: A. Fürstner, N. Shi, Chem. Rev. 1999, 99, 991-1046;
-
Chlorosilanes are also key reagents in manganese-mediated, chromium- and nickel-catalyzed Nozaki-Hiyama-Kishi (NHK) allylation reactions, wherein chlorosilane is proposed to facilitate turnover of the resultant chromium alkoxide; a) For a discussion of the mechanism of manganese-mediated NHK reaction, see: A. Fürstner, N. Shi, Chem. Rev. 1999, 99, 991-1046;
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-
-
-
22
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-
0001470051
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-
Copper salts catalyze the manganese-mediated reaction of allyl chloride with aromatic aldehydes: C. J. Li, Y. Meng, X. H. Yi, J. Ma, T. H. Chan, J. Org. Chem. 1998, 63, 7498-7504.
-
Copper salts catalyze the manganese-mediated reaction of allyl chloride with aromatic aldehydes: C. J. Li, Y. Meng, X. H. Yi, J. Ma, T. H. Chan, J. Org. Chem. 1998, 63, 7498-7504.
-
-
-
-
23
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-
56049101595
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a) J. G. Donkervoort, J. L. Vicario, J. T. B. H. Jastrzebski, R. A. Gossage, G. Cahiez, G. van Koten, J. Organomet. Chem. 1998, 558, 7498-7504;
-
(1998)
J. Organomet. Chem
, vol.558
, pp. 7498-7504
-
-
Donkervoort, J.G.1
Vicario, J.L.2
Jastrzebski, J.T.B.H.3
Gossage, R.A.4
Cahiez, G.5
van Koten, G.6
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24
-
-
0010103769
-
-
b) E. Gallo, E. Solari, C. Floriani, A. Chiesivilla, C. Rizzoli, Organometallics 1995, 14, 2156-2158;
-
(1995)
Organometallics
, vol.14
, pp. 2156-2158
-
-
Gallo, E.1
Solari, E.2
Floriani, C.3
Chiesivilla, A.4
Rizzoli, C.5
-
25
-
-
56049123369
-
-
Higher-order organomanganates have been proposed as intermediates in manganese-catalyzed reactions of Grignard reagents with electrophiles; see ref.[3b
-
[3b].
-
-
-
-
26
-
-
33646440725
-
-
One possible mechanism for catalysis would be activation of the halide toward single electron transfer from Mn0. For activation of allylic bromides by indium salts, see: a G. R. Cook, R. Hayashi, Org. Lett. 2006, 8, 1045-1048;
-
0. For activation of allylic bromides by indium salts, see: a) G. R. Cook, R. Hayashi, Org. Lett. 2006, 8, 1045-1048;
-
-
-
-
28
-
-
27144525212
-
-
An alternative possible mechanism for catalysis would be formation of a nucleophilic allylsilver complex. Silver-catalyzed Sakurai-Hosomi allylation: M. Wadamoto, H. Yamamoto, J. Am. Chem. Soc. 2005, 127, 14556-14557
-
An alternative possible mechanism for catalysis would be formation of a nucleophilic allylsilver complex. Silver-catalyzed Sakurai-Hosomi allylation: M. Wadamoto, H. Yamamoto, J. Am. Chem. Soc. 2005, 127, 14556-14557.
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-
-
-
29
-
-
0032542180
-
-
A moderate yield of benzylated alcohols can be obtained in a silver-catalyzed, zinc-mediated Barbier reaction: L. W. Bieber, E. C. Storch, I. Malvestiti, M. F. da Silva, Tetrahedron Lett. 1998, 39, 9393-9396;
-
a) A moderate yield of benzylated alcohols can be obtained in a silver-catalyzed, zinc-mediated Barbier reaction: L. W. Bieber, E. C. Storch, I. Malvestiti, M. F. da Silva, Tetrahedron Lett. 1998, 39, 9393-9396;
-
-
-
-
30
-
-
43449096041
-
-
Barbier-type reactions mediated by stoichiometric silver iodide and indium: Z.-L. Shen, Y.-L. Yeo, T. P. Loh, J. Org. Chem. 2008, 73, 3922-3924.
-
b) Barbier-type reactions mediated by stoichiometric silver iodide and indium: Z.-L. Shen, Y.-L. Yeo, T. P. Loh, J. Org. Chem. 2008, 73, 3922-3924.
-
-
-
-
31
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-
0001618250
-
-
IMes = 1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene; see: A. J. Arduengo, H. V. R. Dias, J. C. Calabrese, F. Davidson, Organometallics 1993, 12, 3405-3409.
-
IMes = 1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene; see: A. J. Arduengo, H. V. R. Dias, J. C. Calabrese, F. Davidson, Organometallics 1993, 12, 3405-3409.
-
-
-
-
32
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-
56049119096
-
-
Addition of phosphane ligands such as DIFLUORPHOS and MeDuPhos also resulted in lower yields of homoallylic alcohol
-
Addition of phosphane ligands such as DIFLUORPHOS and MeDuPhos also resulted in lower yields of homoallylic alcohol.
-
-
-
-
33
-
-
0032560053
-
-
Copper-catalyzed, manganese-mediated Wurtz coupling in aqueous media: J. H. Ma, T. H. Chan, Tetrahedron Lett. 1998, 39, 2499-2502;
-
a) Copper-catalyzed, manganese-mediated Wurtz coupling in aqueous media: J. H. Ma, T. H. Chan, Tetrahedron Lett. 1998, 39, 2499-2502;
-
-
-
-
34
-
-
0033036003
-
-
10-mediated Wurtz coupling: B. C. Gilbert, C. I. Lindsay, P. T. McGrail, A. F. Parsons, D. T. E. Whittaker, Synth. Commun. 1999, 29, 2711-2718;
-
10-mediated Wurtz coupling: B. C. Gilbert, C. I. Lindsay, P. T. McGrail, A. F. Parsons, D. T. E. Whittaker, Synth. Commun. 1999, 29, 2711-2718;
-
-
-
-
35
-
-
34247258492
-
-
Titaniumand zirconium-catalyzed, manganese-mediated Wurtz coupling: A. F. Barrero, M. M. Herrador, J. F. Q. del Moral, P. Arteaga, J. F. Arteaga, H. R. Dieguez, E. M. Sanchez, J. Org. Chem. 2007, 72, 2988-2995.
-
c) Titaniumand zirconium-catalyzed, manganese-mediated Wurtz coupling: A. F. Barrero, M. M. Herrador, J. F. Q. del Moral, P. Arteaga, J. F. Arteaga, H. R. Dieguez, E. M. Sanchez, J. Org. Chem. 2007, 72, 2988-2995.
-
-
-
-
36
-
-
56049098982
-
-
Certain substrates do not react under our standard allylation conditions. For example, 4-acetamidobenzaldehyde, 4-nitrobenzaldehyde, and 3-hydroxybenzaldehyde afford less than 10% conversion to the requisite homoallylic alcohols.
-
Certain substrates do not react under our standard allylation conditions. For example, 4-acetamidobenzaldehyde, 4-nitrobenzaldehyde, and 3-hydroxybenzaldehyde afford less than 10% conversion to the requisite homoallylic alcohols.
-
-
-
-
37
-
-
6044272959
-
-
Chromium-catalyzed, manganese-mediated pinacol coupling: N. Takenaka, G. Xia, H. Yamamoto, J. Am. Chem. Soc. 2004, 126, 13198-13199.
-
Chromium-catalyzed, manganese-mediated pinacol coupling: N. Takenaka, G. Xia, H. Yamamoto, J. Am. Chem. Soc. 2004, 126, 13198-13199.
-
-
-
-
38
-
-
0034697187
-
-
Rieke manganese has been used to prepare benzylic manganese halides: S. H. Kim, R. D. Rieke, J. Org. Chem. 2000, 65, 2322-2330.
-
Rieke manganese has been used to prepare benzylic manganese halides: S. H. Kim, R. D. Rieke, J. Org. Chem. 2000, 65, 2322-2330.
-
-
-
-
39
-
-
56049105838
-
-
[15b].
-
[15b].
-
-
-
-
41
-
-
27844520946
-
-
J. Einhorn, C. Einhort, J.-L. Luche, Tetrahedron Lett. 1988, 29, 2183-2184.
-
(1988)
Tetrahedron Lett
, vol.29
, pp. 2183-2184
-
-
Einhorn, J.1
Einhort, C.2
Luche, J.-L.3
-
42
-
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33751386227
-
-
E. Kim, D. M. Gordon, W. Schmid, G. M. Whitesides, J. Org. Chem. 1993, 58, 5500-5507.
-
(1993)
J. Org. Chem
, vol.58
, pp. 5500-5507
-
-
Kim, E.1
Gordon, D.M.2
Schmid, W.3
Whitesides, G.M.4
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