-
2
-
-
84989456545
-
-
organo-Li, Mg, Zn, 6, Al, and Cu compounds
-
For reviews, see: (a) Normant, J. F.; Alexakis, A. Synthesis 1981, 841 (organo-Li, Mg, Zn, 6, Al, and Cu compounds). (b) Oppolzer, W. Angew, Chem., Int. Ed. Engl. 1989, 28, 38 (stoichiometric organo-Li, Mg, Zn and catalytic Ni, Pd, Pt compounds). (c) Negishi, E. Pure Appl. Chem. 1981, 53, 2333 (organo-Al/Ti and Al/Zr system). (d) Knochel, P. Comprehensive Organometallic Chemistry II; Able, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, 1995; Vol. 11, p 159 (organo-Li, Mg, Zn, B, Al, Cu, Hg/Pd, Ni, Mn compounds). (e) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, p 865. (f) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207 (organo-Li, Mg, Zn, B, Al compounds).
-
(1981)
Synthesis
, pp. 841
-
-
Normant, J.F.1
Alexakis, A.2
-
3
-
-
84990107570
-
-
stoichiometric organo-Li, Mg, Zn and catalytic Ni, Pd, Pt compounds
-
For reviews, see: (a) Normant, J. F.; Alexakis, A. Synthesis 1981, 841 (organo-Li, Mg, Zn, 6, Al, and Cu compounds). (b) Oppolzer, W. Angew, Chem., Int. Ed. Engl. 1989, 28, 38 (stoichiometric organo-Li, Mg, Zn and catalytic Ni, Pd, Pt compounds). (c) Negishi, E. Pure Appl. Chem. 1981, 53, 2333 (organo-Al/Ti and Al/Zr system). (d) Knochel, P. Comprehensive Organometallic Chemistry II; Able, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, 1995; Vol. 11, p 159 (organo-Li, Mg, Zn, B, Al, Cu, Hg/Pd, Ni, Mn compounds). (e) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, p 865. (f) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207 (organo-Li, Mg, Zn, B, Al compounds).
-
(1989)
Angew, Chem., Int. Ed. Engl.
, vol.28
, pp. 38
-
-
Oppolzer, W.1
-
4
-
-
84937194211
-
-
organo-Al/Ti and Al/Zr system
-
For reviews, see: (a) Normant, J. F.; Alexakis, A. Synthesis 1981, 841 (organo-Li, Mg, Zn, 6, Al, and Cu compounds). (b) Oppolzer, W. Angew, Chem., Int. Ed. Engl. 1989, 28, 38 (stoichiometric organo-Li, Mg, Zn and catalytic Ni, Pd, Pt compounds). (c) Negishi, E. Pure Appl. Chem. 1981, 53, 2333 (organo-Al/Ti and Al/Zr system). (d) Knochel, P. Comprehensive Organometallic Chemistry II; Able, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, 1995; Vol. 11, p 159 (organo-Li, Mg, Zn, B, Al, Cu, Hg/Pd, Ni, Mn compounds). (e) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, p 865. (f) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207 (organo-Li, Mg, Zn, B, Al compounds).
-
(1981)
Pure Appl. Chem.
, vol.53
, pp. 2333
-
-
Negishi, E.1
-
5
-
-
0001342014
-
-
Able, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, organo-Li, Mg, Zn, B, Al, Cu, Hg/Pd, Ni, Mn compounds
-
For reviews, see: (a) Normant, J. F.; Alexakis, A. Synthesis 1981, 841 (organo-Li, Mg, Zn, 6, Al, and Cu compounds). (b) Oppolzer, W. Angew, Chem., Int. Ed. Engl. 1989, 28, 38 (stoichiometric organo-Li, Mg, Zn and catalytic Ni, Pd, Pt compounds). (c) Negishi, E. Pure Appl. Chem. 1981, 53, 2333 (organo-Al/Ti and Al/Zr system). (d) Knochel, P. Comprehensive Organometallic Chemistry II; Able, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, 1995; Vol. 11, p 159 (organo-Li, Mg, Zn, B, Al, Cu, Hg/Pd, Ni, Mn compounds). (e) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, p 865. (f) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207 (organo-Li, Mg, Zn, B, Al compounds).
-
(1995)
Comprehensive Organometallic Chemistry II
, vol.11
, pp. 159
-
-
Knochel, P.1
-
6
-
-
0001522634
-
-
Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford
-
For reviews, see: (a) Normant, J. F.; Alexakis, A. Synthesis 1981, 841 (organo-Li, Mg, Zn, 6, Al, and Cu compounds). (b) Oppolzer, W. Angew, Chem., Int. Ed. Engl. 1989, 28, 38 (stoichiometric organo-Li, Mg, Zn and catalytic Ni, Pd, Pt compounds). (c) Negishi, E. Pure Appl. Chem. 1981, 53, 2333 (organo-Al/Ti and Al/Zr system). (d) Knochel, P. Comprehensive Organometallic Chemistry II; Able, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, 1995; Vol. 11, p 159 (organo-Li, Mg, Zn, B, Al, Cu, Hg/Pd, Ni, Mn compounds). (e) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, p 865. (f) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207 (organo-Li, Mg, Zn, B, Al compounds).
-
(1991)
Comprehensive Organic Synthesis
, vol.4
, pp. 865
-
-
Knochel, P.1
-
7
-
-
4243893500
-
-
organo-Li, Mg, Zn, B, Al compounds
-
For reviews, see: (a) Normant, J. F.; Alexakis, A. Synthesis 1981, 841 (organo-Li, Mg, Zn, 6, Al, and Cu compounds). (b) Oppolzer, W. Angew, Chem., Int. Ed. Engl. 1989, 28, 38 (stoichiometric organo-Li, Mg, Zn and catalytic Ni, Pd, Pt compounds). (c) Negishi, E. Pure Appl. Chem. 1981, 53, 2333 (organo-Al/Ti and Al/Zr system). (d) Knochel, P. Comprehensive Organometallic Chemistry II; Able, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, 1995; Vol. 11, p 159 (organo-Li, Mg, Zn, B, Al, Cu, Hg/Pd, Ni, Mn compounds). (e) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, p 865. (f) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207 (organo-Li, Mg, Zn, B, Al compounds).
-
(1993)
Chem. Rev.
, vol.93
, pp. 2207
-
-
Yamamoto, Y.1
Asao, N.2
-
8
-
-
0345102326
-
-
allyl-Ta
-
(a) Takai, K.; Yamada, M.; Odaka, H.; Utimoto, K.; Fujii, T.; Furukawa, I. Chem. Lett. 1995, 315 (allyl-Ta).
-
(1995)
Chem. Lett.
, vol.31
, pp. 5
-
-
Takai, K.1
Yamada, M.2
Odaka, H.3
Utimoto, K.4
Fujii, T.5
Furukawa, I.6
-
9
-
-
0028145914
-
-
allyl-Zr
-
(b) Takahashi, T.; Kotora, M.; Kasai, K.; Suzuki, N. Tetrahedron Lett. 1994, 35, 5685 (allyl-Zr).
-
(1994)
Tetrahedron Lett.
, vol.35
, pp. 5685
-
-
Takahashi, T.1
Kotora, M.2
Kasai, K.3
Suzuki, N.4
-
10
-
-
0028964910
-
-
allyl-Zn
-
(c) Chatani, N.; Amishiro, N.; Morii, T.; Yamashita, T.; Murai, S. J. Org. Chem. 1995, 60, 1834 (allyl-Zn).
-
(1995)
J. Org. Chem.
, vol.60
, pp. 1834
-
-
Chatani, N.1
Amishiro, N.2
Morii, T.3
Yamashita, T.4
Murai, S.5
-
15
-
-
0001482830
-
-
Lewis acid-catalyzed allyl-Si
-
(h) Yeon, S. H.; Han, J. S.; Hong, E.; Do, Y.; Jung, I. N. J. Organomet. Chem. 1995, 499, 159 (Lewis acid-catalyzed allyl-Si).
-
(1995)
J. Organomet. Chem.
, vol.499
, pp. 159
-
-
Yeon, S.H.1
Han, J.S.2
Hong, E.3
Do, Y.4
Jung, I.N.5
-
16
-
-
0001996468
-
-
Lewis acid-catalyzed allyl-Sn
-
(i) Asao, N.; Matsukawa, Y.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1996, 1513 (Lewis acid-catalyzed allyl-Sn).
-
(1996)
J. Chem. Soc., Chem. Commun.
, pp. 1513
-
-
Asao, N.1
Matsukawa, Y.2
Yamamoto, Y.3
-
18
-
-
33845278851
-
-
Araki, S.; Ito, H.; Butsugan, Y. J. Org. Chem. 1988, 53, 1831.
-
(1988)
J. Org. Chem.
, vol.53
, pp. 1831
-
-
Araki, S.1
Ito, H.2
Butsugan, Y.3
-
19
-
-
0000656554
-
-
(a) Araki, S.; Imai, A.; Shimizu, K.; Yamada, M.; Mori, A.; Butsugan, Y. J. Org. Chem. 1995, 60, 1841.
-
(1995)
J. Org. Chem.
, vol.60
, pp. 1841
-
-
Araki, S.1
Imai, A.2
Shimizu, K.3
Yamada, M.4
Mori, A.5
Butsugan, Y.6
-
20
-
-
0029890653
-
-
(b) Araki, S.; Usui, H.; Kato, M.; Butsugan, Y. J. Am. Chem. Soc. 1996, 118, 4699.
-
(1996)
J. Am. Chem. Soc.
, vol.118
, pp. 4699
-
-
Araki, S.1
Usui, H.2
Kato, M.3
Butsugan, Y.4
-
22
-
-
85047675141
-
-
2O and aqueous/dry THF have been studied: (a) Paquette, L. A.; Mitzel, T. M. Tetrahedron Lett. 1995, 36, 6863. (b) Paquette, L. A.; Mitzel, T. M. J. Am. Chem. Soc. 1996, 118, 1931. (c) Paquette, L. A.; Mitzel, T. M. J. Org. Chem. 1996, 61, 8799.
-
(1995)
Tetrahedron Lett.
, vol.36
, pp. 6863
-
-
Paquette, L.A.1
Mitzel, T.M.2
-
23
-
-
0029933487
-
-
2O and aqueous/dry THF have been studied: (a) Paquette, L. A.; Mitzel, T. M. Tetrahedron Lett. 1995, 36, 6863. (b) Paquette, L. A.; Mitzel, T. M. J. Am. Chem. Soc. 1996, 118, 1931. (c) Paquette, L. A.; Mitzel, T. M. J. Org. Chem. 1996, 61, 8799.
-
(1996)
J. Am. Chem. Soc.
, vol.118
, pp. 1931
-
-
Paquette, L.A.1
Mitzel, T.M.2
-
24
-
-
0039874886
-
-
2O and aqueous/dry THF have been studied: (a) Paquette, L. A.; Mitzel, T. M. Tetrahedron Lett. 1995, 36, 6863. (b) Paquette, L. A.; Mitzel, T. M. J. Am. Chem. Soc. 1996, 118, 1931. (c) Paquette, L. A.; Mitzel, T. M. J. Org. Chem. 1996, 61, 8799.
-
(1996)
J. Org. Chem.
, vol.61
, pp. 8799
-
-
Paquette, L.A.1
Mitzel, T.M.2
-
25
-
-
0000125198
-
-
Fujiwara, N.; Yamamoto, Y. J. Org. Chem. 1997, 62, 2318. See also: Ranu, B. C.; Majee, A. J. Chem. Soc., Chem. Commun. 1997, 1225.
-
(1997)
J. Org. Chem.
, vol.62
, pp. 2318
-
-
Fujiwara, N.1
Yamamoto, Y.2
-
26
-
-
0002747434
-
-
Fujiwara, N.; Yamamoto, Y. J. Org. Chem. 1997, 62, 2318. See also: Ranu, B. C.; Majee, A. J. Chem. Soc., Chem. Commun. 1997, 1225.
-
(1997)
J. Chem. Soc., Chem. Commun.
, pp. 1225
-
-
Ranu, B.C.1
Majee, A.2
-
28
-
-
0345533760
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-
note
-
2) group acts as a ligand of the In complex (ref 4). Accordingly, if the addition of the indium reagents to acetylenes proceeds in quantitative yield, 0.5 equiv of the reagents are needed for 1 equiv of acetylenes. Normally, we used 0.6 equiv of the reagents toward 1 equiv of acetylenes.
-
-
-
-
30
-
-
0344671431
-
-
note
-
The allylation of TMS-substituted alkynes with allylzinc bromide gives the same regioselectivity as the present allylindation (ref 3d).
-
-
-
-
31
-
-
0042558160
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-
A double-zincation intermediate was proposed in the allylzincation of terminal alkynes: Frangin, Y.; Gaudemar, M. J. Organomet. Chem. 1977, 142, 9. See also: Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, p 883.
-
(1977)
J. Organomet. Chem.
, vol.142
, pp. 9
-
-
Frangin, Y.1
Gaudemar, M.2
-
32
-
-
0345102313
-
-
Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford
-
A double-zincation intermediate was proposed in the allylzincation of terminal alkynes: Frangin, Y.; Gaudemar, M. J. Organomet. Chem. 1977, 142, 9. See also: Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, p 883.
-
(1991)
Comprehensive Organic Synthesis
, vol.4
, pp. 883
-
-
Knochel, P.1
-
33
-
-
33847801217
-
-
The stereoselectivity of the addition of aluminum hydride to alkynes was precisely studied. According to the study, the transcarbometalation product is favored thermodynamically under high-temperature reaction conditions: Eisch, J. J.; Rhee, S.-G. J. Am. Chem. Soc. 1975, 97, 4673. See also ref 2d, p 280.
-
(1975)
J. Am. Chem. Soc.
, vol.97
, pp. 4673
-
-
Eisch, J.J.1
Rhee, S.-G.2
-
34
-
-
0344239983
-
-
note
-
Negishi et al. reported the palladium-catalyzed coupling reaction of vinylic bromides and alkenylalane, which was prepared in situ from alkynes and alkylaluminum hydride (ref 2c).
-
-
-
-
35
-
-
0345102311
-
-
note
-
In the three-component coupling reaction, a fair amount of byproducts (mono- and dibenzylation products 18a and 22, respectively) were formed along with 21.
-
-
-
-
36
-
-
0344671429
-
-
note
-
1H NMR and GC-MS showed that 22 was obtained as a single stereoisomer. The Z-conformation were assigned by the analogy from the result of 18a-d (Scheme 2).
-
-
-
-
37
-
-
0345533757
-
-
note
-
2-Pd-(II)X′ species, which would undergo the transmetalation reaction with the vinylindium 20 to give the vinylpalladium intermediate. Reductive elimination would give the three-component coupling product along with the Pd(0) catalyst.
-
-
-
-
38
-
-
0345102310
-
-
note
-
4
-
-
-
-
39
-
-
0345533756
-
-
note
-
The protonation would take place at the workup stage: normally, an acidic silica gel column was used (see Experimental Section). On the other hand, when the reaction was quenched with diluted HCl, the desired allylation - enamination product was not obtained.
-
-
-
-
41
-
-
0000017202
-
-
Stork, G.; Terrell, R.; Szmuszkovicz, J. J. Am. Chem. Soc. 1954, 76, 2029.
-
(1954)
J. Am. Chem. Soc.
, vol.76
, pp. 2029
-
-
Stork, G.1
Terrell, R.2
Szmuszkovicz, J.3
-
43
-
-
33947460354
-
-
(a) Leonard, N. J.; Hay, A. S.; Fulmer, R. W.; Gash, V. W. J. Am. Chem. Soc. 1955, 77, 439.
-
(1955)
J. Am. Chem. Soc.
, vol.77
, pp. 439
-
-
Leonard, N.J.1
Hay, A.S.2
Fulmer, R.W.3
Gash, V.W.4
-
44
-
-
0025203660
-
-
(b) Katritzky, A. R.; Long, Q.-H.; Lue, P.; Jozwiak, A. Tetrahedron 1990, 46, 8153.
-
(1990)
Tetrahedron
, vol.46
, pp. 8153
-
-
Katritzky, A.R.1
Long, Q.-H.2
Lue, P.3
Jozwiak, A.4
-
46
-
-
0002248149
-
-
(d) Broekhof, N. L. J. M.; Jonkers, F. L.; van der Gen, A. Tetrahedron Lett. 1980, 21, 2671.
-
(1980)
Tetrahedron Lett.
, vol.21
, pp. 2671
-
-
Broekhof, N.L.J.M.1
Jonkers, F.L.2
Van Der Gen, A.3
-
47
-
-
0001158461
-
-
(e) Bekker, B. H.; A-Lim, D. S. T.; van der Gen, A. Tetrahedron Lett. 1984, 25, 4259.
-
(1984)
Tetrahedron Lett.
, vol.25
, pp. 4259
-
-
Bekker, B.H.1
A-Lim, D.S.T.2
Van Der Gen, A.3
-
48
-
-
0001727152
-
-
(f) Comi, R.; Franck, R. W.; Reitano, M.; Weinreb, S. M. Tetrahedron Lett. 1973, 3107.
-
(1973)
Tetrahedron Lett.
, pp. 3107
-
-
Comi, R.1
Franck, R.W.2
Reitano, M.3
Weinreb, S.M.4
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