-
2
-
-
0001522634
-
-
(Eds.: B. M. Trost, I. Fleming, M. F. Semmelhack), Pergamon, New York
-
b) P. Knochel in Comprehensive Organic Synthesis, Vol. 4 (Eds.: B. M. Trost, I. Fleming, M. F. Semmelhack), Pergamon, New York, 1991, pp. 865-911;
-
(1991)
Comprehensive Organic Synthesis
, vol.4
, pp. 865-911
-
-
Knochel, P.1
-
3
-
-
0001773192
-
-
(Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim
-
c) I. Marek, J. F. Normant in Metal-Catalyzed Cross-Coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1998, pp. 271-337;
-
(1998)
Metal-Catalyzed Cross-Coupling Reactions
, pp. 271-337
-
-
Marek, I.1
Normant, J.F.2
-
5
-
-
0000725304
-
-
a) E. Shirakawa, H. Yoshida, T. Kurahashi, Y. Nakao, T. Hiyama, J. Am. Chem. Soc. 1998, 120, 2975-2976;
-
(1998)
J. Am. Chem. Soc.
, vol.120
, pp. 2975-2976
-
-
Shirakawa, E.1
Yoshida, H.2
Kurahashi, T.3
Nakao, Y.4
Hiyama, T.5
-
6
-
-
0033520681
-
-
b) E. Shirakawa, K. Yamasaki, H. Yoshida, T. Hiyama, J. Am. Chem. Soc. 1999, 121, 10 221-10 222;
-
(1999)
J. Am. Chem. Soc.
, vol.121
, pp. 10221-10222
-
-
Shirakawa, E.1
Yamasaki, K.2
Yoshida, H.3
Hiyama, T.4
-
7
-
-
0000171394
-
-
c) E. Shirakawa, H. Yoshida, Y. Nakao, T. Hiyama, Org. Lett. 2000, 2, 2209-2211;
-
(2000)
Org. Lett.
, vol.2
, pp. 2209-2211
-
-
Shirakawa, E.1
Yoshida, H.2
Nakao, Y.3
Hiyama, T.4
-
8
-
-
0034504429
-
-
d) H. Yoshida, E. Shirakawa, T. Kurahashi, Y. Nakao, T. Hiyama, Organometallics 2000, 19, 5671-5678;
-
(2000)
Organometallics
, vol.19
, pp. 5671-5678
-
-
Yoshida, H.1
Shirakawa, E.2
Kurahashi, T.3
Nakao, Y.4
Hiyama, T.5
-
9
-
-
0034248709
-
-
e) R. Hua, S. Onozawa, M. Tanaka, Organometallics 2000, 19, 3269-3271;
-
(2000)
Organometallics
, vol.19
, pp. 3269-3271
-
-
Hua, R.1
Onozawa, S.2
Tanaka, M.3
-
10
-
-
0035823698
-
-
f) E. Shirakawa, Y. Yamamoto, Y. Nakao, T. Tsuchimoto, T. Hiyama, Chem. Commun. 2001, 1926-1927;
-
(2001)
Chem. Commun.
, pp. 1926-1927
-
-
Shirakawa, E.1
Yamamoto, Y.2
Nakao, Y.3
Tsuchimoto, T.4
Hiyama, T.5
-
11
-
-
0344875110
-
-
g) B. Martín-Matute, E. Buñuel, M. Méndez, C. Nieto-Oberhuber, D. J. Cárdenas, A. M. Echavarren, J. Organomet. Chem. 2003, 687, 410-419;
-
(2003)
J. Organomet. Chem.
, vol.687
, pp. 410-419
-
-
Martín-Matute, B.1
Buñuel, E.2
Méndez, M.3
Nieto-Oberhuber, C.4
Cárdenas, D.J.5
Echavarren, A.M.6
-
12
-
-
33746293749
-
-
h) E. Shirakawa, Y. Yamamoto, Y. Nakao, S. Oda, T. Tsuchimoto, T. Hiyama, Angew. Chem. 2004, 116, 3530-3533;
-
(2004)
Angew. Chem.
, vol.116
, pp. 3530-3533
-
-
Shirakawa, E.1
Yamamoto, Y.2
Nakao, Y.3
Oda, S.4
Tsuchimoto, T.5
Hiyama, T.6
-
13
-
-
4544257657
-
-
Angew. Chem. Int. Ed. 2004, 43, 3448-3451;
-
(2004)
Angew. Chem. Int. Ed.
, vol.43
, pp. 3448-3451
-
-
-
16
-
-
0001996468
-
-
The allylstannylation of alkynes through the nucleophilic addition of allylstannanes across alkynes activated by a Lewis acid is known, see: a) N. Asao, Y. Matsukawa, Y. Yamamoto, Chem. Commun. 1996, 1513-1514;
-
(1996)
Chem. Commun.
, pp. 1513-1514
-
-
Asao, N.1
Matsukawa, Y.2
Yamamoto, Y.3
-
17
-
-
0033583167
-
-
b) Y. Matsukawa, N. Asao, H. Kitahara, Y. Yamamoto, Tetrahedron 1999, 55, 3779-3790;
-
(1999)
Tetrahedron
, vol.55
, pp. 3779-3790
-
-
Matsukawa, Y.1
Asao, N.2
Kitahara, H.3
Yamamoto, Y.4
-
18
-
-
0030592707
-
-
for the radical-mediated allylstannylation of alkynes, see: c) K. Miura, D. Itoh, T. Honda, H. Saito, H. Ito, A. Hosomi, Tetrahedron Lett. 1996, 37, 8539-8542.
-
(1996)
Tetrahedron Lett.
, vol.37
, pp. 8539-8542
-
-
Miura, K.1
Itoh, D.2
Honda, T.3
Saito, H.4
Ito, H.5
Hosomi, A.6
-
19
-
-
37049139551
-
-
For alkynylstannanes, see: a) B. Cetinkaya, M. F. Lappert, J. McMeeking, D. E. Palmer, J. Chem. Soc., Dalton Trans. 1973, 1202-1208;
-
(1973)
J. Chem. Soc., Dalton Trans.
, pp. 1202-1208
-
-
Cetinkaya, B.1
Lappert, M.F.2
McMeeking, J.3
Palmer, D.E.4
-
20
-
-
0030741227
-
-
b) E. Shirakawa, H. Yoshida, T. Hiyama, Tetrahedron Lett. 1997, 38, 5177-5180;
-
(1997)
Tetrahedron Lett.
, vol.38
, pp. 5177-5180
-
-
Shirakawa, E.1
Yoshida, H.2
Hiyama, T.3
-
21
-
-
0031860749
-
-
c) M. Herberhold, U. Steffl, W. Milius, B. Wrackmeyer, Chem. Eur. J. 1998, 4, 1027-1032;
-
(1998)
Chem. Eur. J.
, vol.4
, pp. 1027-1032
-
-
Herberhold, M.1
Steffl, U.2
Milius, W.3
Wrackmeyer, B.4
-
22
-
-
0038336919
-
-
d) T. Matsubara, K. Hirao, Organometallics 2002, 21, 4482-4489; for allyl and acylstannanes, see references [2g] and [2e], respectively.
-
(2002)
Organometallics
, vol.21
, pp. 4482-4489
-
-
Matsubara, T.1
Hirao, K.2
-
23
-
-
37049094646
-
-
Many reports on the oxidative addition of organostannanes to platinum(0) complexes are available, see: a) C. Eaborn, A. Pidcock, B. R. Steele, J. Chem. Soc., Dalton Trans. 1976, 767-776;
-
(1976)
J. Chem. Soc., Dalton Trans.
, pp. 767-776
-
-
Eaborn, C.1
Pidcock, A.2
Steele, B.R.3
-
25
-
-
0001917999
-
-
c) G. Butler, C. Eaborn, A. Pidcock, J. Organomet. Chem. 1979, 181, 47-59;
-
(1979)
J. Organomet. Chem.
, vol.181
, pp. 47-59
-
-
Butler, G.1
Eaborn, C.2
Pidcock, A.3
-
26
-
-
84909707739
-
-
d) C. Eaborn, K. Kundu, A. Pidcock, J. Chem. Soc., Dalton Trans. 1981, 1223-1332.
-
(1981)
J. Chem. Soc., Dalton Trans.
, pp. 1223-1332
-
-
Eaborn, C.1
Kundu, K.2
Pidcock, A.3
-
27
-
-
0034029281
-
-
The palladium-catalyzed arylstannylation of norbornene using aryl(trichloro)stannanes has been proposed to proceed through the oxidative addition of an Ar-Sn bond to palladium(0) complexes, see: a) K. Fugami, Y. Mishiba, S. Hagiwara, D. Koyama, M. Kameyama, M. Kosugi, Synlett 2000, 553-555;
-
(2000)
Synlett
, pp. 553-555
-
-
Fugami, K.1
Mishiba, Y.2
Hagiwara, S.3
Koyama, D.4
Kameyama, M.5
Kosugi, M.6
-
28
-
-
0034986271
-
-
aryl- and alkenylstannanes undergo the palladium-catalyzed dimerization/carbostannylation of alkynes not through oxidative addition but through the reaction with palladacyclopentadienes; see: b) H. Yoshida, E. Shirakawa, Y. Nakao, Y. Honda, T. Hiyama, Bull. Chem. Soc. Jpn. 2001, 74, 637-647.
-
(2001)
Bull. Chem. Soc. Jpn.
, vol.74
, pp. 637-647
-
-
Yoshida, H.1
Shirakawa, E.2
Nakao, Y.3
Honda, Y.4
Hiyama, T.5
-
29
-
-
0000685605
-
-
Acyl(tributyl)stannanes are readily prepared by the reaction of aldehydes with tributylstannylmagnesium or -lithium reagents, see: a) M. Kosugi, H. Naka, T. Sano, T. Migita, Bull. Chem. Soc. Jpn. 1987, 60, 3462-3464;
-
(1987)
Bull. Chem. Soc. Jpn.
, vol.60
, pp. 3462-3464
-
-
Kosugi, M.1
Naka, H.2
Sano, T.3
Migita, T.4
-
30
-
-
0013128314
-
-
b) J. A. Marshall, A. W. Garofalo, K. W. Hinke, Org. Synth. 1999, 77, 98-106.
-
(1999)
Org. Synth.
, vol.77
, pp. 98-106
-
-
Marshall, J.A.1
Garofalo, A.W.2
Hinke, K.W.3
-
31
-
-
3643112634
-
-
For decarbonylative 1,4-carbosilylation of 1,3-dienes through three-component coupling, see: a) Y. Obora, Y. Tsuji, T. Kawamura, J. Am. Chem. Soc. 1995, 117, 9814-9821;
-
(1995)
J. Am. Chem. Soc.
, vol.117
, pp. 9814-9821
-
-
Obora, Y.1
Tsuji, Y.2
Kawamura, T.3
-
32
-
-
0000398571
-
-
b) Y. Obora, Y. Tsuji, T. Kawamura, J. Am. Chem. Soc. 1993, 115, 10 414-10 415.
-
(1993)
J. Am. Chem. Soc.
, vol.115
, pp. 10414-10415
-
-
Obora, Y.1
Tsuji, Y.2
Kawamura, T.3
-
33
-
-
33746322949
-
-
note
-
The use of other ethereal solvents, such as THF, 1,4-dioxane, 1,2-dimethoxyethane (DME), toluene, and dimethyl formamide (DMF), gave inferior results.
-
-
-
-
34
-
-
0034692348
-
-
2] in the absence of an unsaturated compound, see: E. Shirakawa, Y. Nakao, H. Yoshida, T. Hiyama, J. Am. Chem. Soc. 2000, 122, 9030-9031.
-
(2000)
J. Am. Chem. Soc.
, vol.122
, pp. 9030-9031
-
-
Shirakawa, E.1
Nakao, Y.2
Yoshida, H.3
Hiyama, T.4
-
35
-
-
0000665822
-
-
A similar regioselective insertion of propargyl pivalate into a H-Pt bond has been proposed, see: G. Stork, M. E. Jung, E. Colvin, Y. Noel, J. Am. Chem. Soc. 1974, 96, 3684-3686.
-
(1974)
J. Am. Chem. Soc.
, vol.96
, pp. 3684-3686
-
-
Stork, G.1
Jung, M.E.2
Colvin, E.3
Noel, Y.4
-
36
-
-
0001445927
-
-
Acyl-palladium intermediates are reluctant to undergo decarbonylation (≈200°C), as observed in the palladium-catalyzed decarbonylation of acyl halides or aldehydes, whereas the presence of an alkene and/or a base accelerates decarbonylation in the decarbonylative coupling reaction of acid chlorides with alkenes; see reference [8] and a) J. O. Hawthorne, M. H. Wilt, J. Org. Chem. 1960, 25, 2215-2216;
-
(1960)
J. Org. Chem.
, vol.25
, pp. 2215-2216
-
-
Hawthorne, J.O.1
Wilt, M.H.2
-
38
-
-
0000475761
-
-
c) J. W. Verbicky, Jr., B. A. Dellacoletta, L. Williams, Tetrahedron Lett. 1982, 23, 371-372;
-
(1982)
Tetrahedron Lett.
, vol.23
, pp. 371-372
-
-
Verbicky Jr., J.W.1
Dellacoletta, B.A.2
Williams, L.3
-
40
-
-
33847085177
-
-
No side products, such as a hydrostannylation product derived from β-hydride elimination, were observed during the reaction of tributyl(propanoyl)stannane (Table 2, entry 7), thus implying rapid reductive elimination from 6; for CO-induced reductive elimination, see: T. Yamamoto, J. Ishizu, T. Kohara, S. Komiya, A. Yamamoto, J. Am. Chem. Soc. 1980, 102, 3758-3764.
-
(1980)
J. Am. Chem. Soc.
, vol.102
, pp. 3758-3764
-
-
Yamamoto, T.1
Ishizu, J.2
Kohara, T.3
Komiya, S.4
Yamamoto, A.5
-
41
-
-
33746290351
-
-
note
-
The reaction under identical conditions to entry 4 in Table 2 but under a CO atmosphere (1 atm) gave adduct 3i in less than 20% yield, and no trace amounts of a non-decarbonylative adduct, such as 8, was observed.
-
-
-
|