-
1
-
-
77956990841
-
-
Hou, X.-L.; Yang, Z.; Wong, H. N. C. Prog. Heterocycl. Chem. 2002, 14, 139-179.
-
(2002)
Prog. Heterocycl. Chem.
, vol.14
, pp. 139-179
-
-
Hou, X.-L.1
Yang, Z.2
Wong, H.N.C.3
-
2
-
-
0032891112
-
-
(a) Alali, F. Q.; Liu, X.-X.; McLaughlin, J. L. J. Nat. Prod. 1999, 62, 504-540.
-
(1999)
J. Nat. Prod.
, vol.62
, pp. 504-540
-
-
Alali, F.Q.1
Liu, X.-X.2
McLaughlin, J.L.3
-
4
-
-
0032145138
-
-
(c) Zafra-Polo, M. C.; Figadere, B.; Gallardo, T.; Tormo, J. R.; Cortes, D. Phytochemistry 1998, 48, 1087-1117.
-
(1998)
Phytochemistry
, vol.48
, pp. 1087-1117
-
-
Zafra-Polo, M.C.1
Figadere, B.2
Gallardo, T.3
Tormo, J.R.4
Cortes, D.5
-
13
-
-
84950086559
-
-
(b) Semmelhack, M. F.; Kim, C.; Zhang, N.; Bodurow, C.; Sanner, M.; Dobler, W.; Meier, M. Pure Appl. Chem. 1990, 62, 2035-2040.
-
(1990)
Pure Appl. Chem.
, vol.62
, pp. 2035-2040
-
-
Semmelhack, M.F.1
Kim, C.2
Zhang, N.3
Bodurow, C.4
Sanner, M.5
Dobler, W.6
Meier, M.7
-
18
-
-
0026325945
-
-
(g) Gracza, T.; Hasenöhrl, T.; Stahl, U.; Jäger, V. Synthesis 1991, 1108-1118.
-
(1991)
Synthesis
, pp. 1108-1118
-
-
Gracza, T.1
Hasenöhrl, T.2
Stahl, U.3
Jäger, V.4
-
20
-
-
1242269280
-
-
A portion of this work has been previously communicated. See: Wolfe, J. P.; Rossi, M. A. J. Am. Chem. Soc. 2004, 126, 1620-1621.
-
(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 1620-1621
-
-
Wolfe, J.P.1
Rossi, M.A.2
-
21
-
-
4544265647
-
-
For related transformations of γ-aminoalkenes that afford nitrogen heterocycles, see: (a) Ney, J. E.; Wolfe, J. P. Angew. Chem., Int. Ed. 2004, 43, 3605-3608. (b) Lira, R.; Wolfe, J. P. J. Am. Chem. Soc. 2004, 126, 13906-13907.
-
(2004)
Angew. Chem., Int. Ed.
, vol.43
, pp. 3605-3608
-
-
Ney, J.E.1
Wolfe, J.P.2
-
22
-
-
7444269099
-
-
For related transformations of γ-aminoalkenes that afford nitrogen heterocycles, see: (a) Ney, J. E.; Wolfe, J. P. Angew. Chem., Int. Ed. 2004, 43, 3605-3608. (b) Lira, R.; Wolfe, J. P. J. Am. Chem. Soc. 2004, 126, 13906-13907.
-
(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 13906-13907
-
-
Lira, R.1
Wolfe, J.P.2
-
23
-
-
0142089062
-
-
For related transformations of γ-alkylidene malonates that afford carbocycles see: (a) Balme, G.; Bouyssi, D.; Lomberget, T.; Monteiro, N. Synthesis 2003, 2115-2134. (b) Balme, G.; Bouyssi, D.; Faure, R.; Gore, J.; Van Hemelryck, B. Tetrahedron 1992, 48, 3891-3902.
-
(2003)
Synthesis
, pp. 2115-2134
-
-
Balme, G.1
Bouyssi, D.2
Lomberget, T.3
Monteiro, N.4
-
24
-
-
0026594326
-
-
For related transformations of γ-alkylidene malonates that afford carbocycles see: (a) Balme, G.; Bouyssi, D.; Lomberget, T.; Monteiro, N. Synthesis 2003, 2115-2134. (b) Balme, G.; Bouyssi, D.; Faure, R.; Gore, J.; Van Hemelryck, B. Tetrahedron 1992, 48, 3891-3902.
-
(1992)
Tetrahedron
, vol.48
, pp. 3891-3902
-
-
Balme, G.1
Bouyssi, D.2
Faure, R.3
Gore, J.4
Van Hemelryck, B.5
-
25
-
-
0032981402
-
-
For related transformations of γ-hydroxy allenes, see: (a) Kang, S.-K.; Baik, T.-G.; Kulak, A. N. Synlett 1999, 324-326. (b) Walkup, R. D.; Guan, L.; Mosher, M. D.; Kim, S. W.; Kim, Y. S. Synlett 1993, 88-90.
-
(1999)
Synlett
, pp. 324-326
-
-
Kang, S.-K.1
Baik, T.-G.2
Kulak, A.N.3
-
26
-
-
85058223555
-
-
For related transformations of γ-hydroxy allenes, see: (a) Kang, S.-K.; Baik, T.-G.; Kulak, A. N. Synlett 1999, 324-326. (b) Walkup, R. D.; Guan, L.; Mosher, M. D.; Kim, S. W.; Kim, Y. S. Synlett 1993, 88-90.
-
(1993)
Synlett
, pp. 88-90
-
-
Walkup, R.D.1
Guan, L.2
Mosher, M.D.3
Kim, S.W.4
Kim, Y.S.5
-
27
-
-
0001227038
-
-
For related transformations of γ-hydroxy alkynes, see: Luo, F. T.; Schreuder, I.; Wang, R. T. J. Org. Chem. 1992, 57, 2213-2215.
-
(1992)
J. Org. Chem.
, vol.57
, pp. 2213-2215
-
-
Luo, F.T.1
Schreuder, I.2
Wang, R.T.3
-
28
-
-
0029042650
-
-
For related heteroannulations of internal alkynes with o-haloanilines, o-halophenols, and related compounds, see: Larock, R. C.; Yum, E. K.; Doty, M. J.; Sham, K. K. C. J. Org. Chem. 1995, 60, 3270-3271.
-
(1995)
J. Org. Chem.
, vol.60
, pp. 3270-3271
-
-
Larock, R.C.1
Yum, E.K.2
Doty, M.J.3
Sham, K.K.C.4
-
29
-
-
0024803101
-
-
Small amounts of 5-aryl-4-penten-1-ol products were also observed. See: Larock, R. C.; Leung, W.-Y.; Stoltz-Dunn, S. Tetrahedron Lett. 1989, 30, 6629-6632.
-
(1989)
Tetrahedron Lett.
, vol.30
, pp. 6629-6632
-
-
Larock, R.C.1
Leung, W.-Y.2
Stoltz-Dunn, S.3
-
31
-
-
84943961926
-
-
Trost has noted the formation of a tetrahydrofuran side product in the Heck arylation of an enyne bearing a secondary OH group and suggested a mechanism of intermolecular carbopalladation to account for its formation. See: Trost, B. M.; Pfrengle, W.; Urabe, H.; Dumas, J. J. Am. Chem. Soc. 1992, 114, 1923-1924.
-
(1992)
J. Am. Chem. Soc.
, vol.114
, pp. 1923-1924
-
-
Trost, B.M.1
Pfrengle, W.2
Urabe, H.3
Dumas, J.4
-
34
-
-
0042865830
-
-
(a) Jensen, D. R.; Schultz, M. J.; Mueller, J. A.; Sigman, M. S. Angew. Chem., Int. Ed. 2003, 42, 3810-3813.
-
(2003)
Angew. Chem., Int. Ed.
, vol.42
, pp. 3810-3813
-
-
Jensen, D.R.1
Schultz, M.J.2
Mueller, J.A.3
Sigman, M.S.4
-
35
-
-
0012253713
-
-
and references therein
-
(b) Steinhoff, B. A.; Stahl, S. S. Org. Lett. 2002, 4, 4179-4181 and references therein.
-
(2002)
Org. Lett.
, vol.4
, pp. 4179-4181
-
-
Steinhoff, B.A.1
Stahl, S.S.2
-
36
-
-
17444424355
-
-
note
-
Ligand abbreviations: dppe = 1,2-bis(diphenylphosphino)ethane; BINAP = 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl; dppf = 1,1′-bis(diphenylphosphino)ferrocene; dppb = 1,1′- bis(diphenylphosphino)butane; xantphos = 9,9-dimethyl-4,5-bis(diphenylphosphino) xanthene; dpe-phos = bis(2-diphenylphosphinophenyl)ether. All ligands are readily available from commercial sources.
-
-
-
-
37
-
-
17444376126
-
-
note
-
Most reactions proceeded to completion in ca. 2 h as judged by GC analysis of crude reaction mixtures.
-
-
-
-
38
-
-
17444403649
-
-
note
-
1H NMR and GC.
-
-
-
-
39
-
-
17444362010
-
-
note
-
It is likely that oxidation of the alcohol accompanies reduction of the aryl bromide. However, the aldehyde side products that would be generated in this process were not detected and are likely unstable under the reaction conditions. See ref 17.
-
-
-
-
40
-
-
17444425823
-
-
note
-
Only trace amounts of side products derived from Heck arylation of the olefin were detected.
-
-
-
-
41
-
-
17444421639
-
-
note
-
13C NMR spectroscopy and MS. See the Supporting Information.
-
-
-
-
42
-
-
17444366272
-
-
note
-
Stereochemistry of tetrahydrofuran products was established by nOe experiments or by comparison of NMR spectra to related compounds of known configuration. See the Supporting Information for complete details.
-
-
-
-
43
-
-
17444386784
-
-
note
-
1H NMR and/or GC analysis of crude reaction mixtures.
-
-
-
-
45
-
-
0001567673
-
-
(b) Jager, J.; Graafland, T.; Schenk, H.; Kirby, A. J.; Engberts, J. B. F. N. J. Am. Chem. Soc. 1984, 106, 139-143.
-
(1984)
J. Am. Chem. Soc.
, vol.106
, pp. 139-143
-
-
Jager, J.1
Graafland, T.2
Schenk, H.3
Kirby, A.J.4
Engberts, J.B.F.N.5
-
47
-
-
0000699103
-
-
(b) Bryndza, H. E.; Calabrese, J. C.; Wreford, S. S. Organometallics 1984, 3, 1603-1604.
-
(1984)
Organometallics
, vol.3
, pp. 1603-1604
-
-
Bryndza, H.E.1
Calabrese, J.C.2
Wreford, S.S.3
-
48
-
-
1642300603
-
-
(c) Hayashi, T.; Yamasaki, K.; Mimura, M.; Uozumi, Y. J. Am. Chem. Soc. 2004, 126, 3036-3037.
-
(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 3036-3037
-
-
Hayashi, T.1
Yamasaki, K.2
Mimura, M.3
Uozumi, Y.4
-
50
-
-
17444404290
-
-
note
-
Tetrafluoroethylene undergoes selective insertion into the Pt-O bond of (dppe)Pt(Me)(OMe). See ref 28a,b.
-
-
-
-
51
-
-
17444394574
-
-
note
-
Related transformations of γ-aminoalkenes to pyrrolidines have been shown to proceed through an analogous mechanism. Experimental evidence in the pyrrolidine-forming reactions supports the idea that alkene insertion occurs into the Pd-heteroatom bond rather than the Pd-carbon bond. See ref 9a.
-
-
-
-
52
-
-
17444387532
-
-
note
-
Although we currently favor this mechanism, an alternative mechanism involving alkene insertion into the Pd-C bond followed by C-O bond-forming reductive elimination cannot be unambiguously ruled out in all instances. This mechanistic pathway would also likely proceed via a cyclic, chelated intermediate such as 32, or 35. High 1,4 asymmetric induction would be unlikely if insertion into the Pd-C bond occurred from an acyclic, unchelated intermediate. For further details, see ref 8.
-
-
-
-
53
-
-
0038276962
-
-
There is a significant buildup of positive charge on the C1 carbon in the transition state leading to β-elimination. Thus, substrates bearing electron-donating C1 substituents are more prone to β-elimination than substrates with electron-withdrawing substituents. See: Mueller, J. A.; Sigman, M. S. J. Am. Chem. Soc. 2003, 125, 7005-7013.
-
(2003)
J. Am. Chem. Soc.
, vol.125
, pp. 7005-7013
-
-
Mueller, J.A.1
Sigman, M.S.2
-
54
-
-
0029890191
-
-
For a discussion on the effect of Pt-O bond strength on rates of CO insertion, see: Dockter, D. W.; Fanwick, P. E.; Kubiak, C. P. J. Am. Chem. Soc. 1996, 118, 4846-4852.
-
(1996)
J. Am. Chem. Soc.
, vol.118
, pp. 4846-4852
-
-
Dockter, D.W.1
Fanwick, P.E.2
Kubiak, C.P.3
-
55
-
-
17444397541
-
-
note
-
The insertion of tetrafluoroethylene into the Pt-O bond of (dppe)Pt(Me)(OMe) has been shown to occur through a five-coordinate intermediate. See ref 28a.
-
-
-
-
56
-
-
0032496939
-
-
For a discussion of mechanistic issues in related alkene insertions into Pd-C bonds, see: (a) Ashimori, A.; Bachand, B.; Calter, M. A.; Govek, S. P.; Overman, L. E.; Poon, D. J. J. Am. Chem. Soc. 1998, 120, 6488-6499. (b) Oestreich, M.; Sempere-Culler, F.; Machotta, A. B. Angew. Chem., Int. Ed. 2005, 44, 149-152. (c) Samsel, E. G.; Norton, J. R. J. Am. Chem. Soc. 1984, 106, 5505-5512.
-
(1998)
J. Am. Chem. Soc.
, vol.120
, pp. 6488-6499
-
-
Ashimori, A.1
Bachand, B.2
Calter, M.A.3
Govek, S.P.4
Overman, L.E.5
Poon, D.J.6
-
57
-
-
11244311586
-
-
For a discussion of mechanistic issues in related alkene insertions into Pd-C bonds, see: (a) Ashimori, A.; Bachand, B.; Calter, M. A.; Govek, S. P.; Overman, L. E.; Poon, D. J. J. Am. Chem. Soc. 1998, 120, 6488-6499. (b) Oestreich, M.; Sempere-Culler, F.; Machotta, A. B. Angew. Chem., Int. Ed. 2005, 44, 149-152. (c) Samsel, E. G.; Norton, J. R. J. Am. Chem. Soc. 1984, 106, 5505-5512.
-
(2005)
Angew. Chem., Int. Ed.
, vol.44
, pp. 149-152
-
-
Oestreich, M.1
Sempere-Culler, F.2
Machotta, A.B.3
-
58
-
-
0021497508
-
-
For a discussion of mechanistic issues in related alkene insertions into Pd-C bonds, see: (a) Ashimori, A.; Bachand, B.; Calter, M. A.; Govek, S. P.; Overman, L. E.; Poon, D. J. J. Am. Chem. Soc. 1998, 120, 6488-6499. (b) Oestreich, M.; Sempere-Culler, F.; Machotta, A. B. Angew. Chem., Int. Ed. 2005, 44, 149-152. (c) 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
-
59
-
-
0001663666
-
-
Wilkinson, G., Guard, R. D., McCleverty, J. A., Eds.; Pergamon: Oxford
-
(a) Tobe, M. L. In Comprehensive Coordination Chemistry; Wilkinson, G., Guard, R. D., McCleverty, J. A., Eds.; Pergamon: Oxford, 1987; Vol. 1, pp 281-329.
-
(1987)
Comprehensive Coordination Chemistry
, vol.1
, pp. 281-329
-
-
Tobe, M.L.1
-
61
-
-
4544245811
-
-
3. See: (a) Bartolome, C.; Espinet, P.; Martin-Alvarez, J. M.; Villafane, F. Eur. J. Inorg. Chem. 2004, 2326-2337. (b) Louie, J.; Hartwig, J. F. J. Am. Chem. Soc. 1995, 117, 11598-11599.
-
(2004)
Eur. J. Inorg. Chem.
, pp. 2326-2337
-
-
Bartolome, C.1
Espinet, P.2
Martin-Alvarez, J.M.3
Villafane, F.4
-
62
-
-
0000008345
-
-
3. See: (a) Bartolome, C.; Espinet, P.; Martin-Alvarez, J. M.; Villafane, F. Eur. J. Inorg. Chem. 2004, 2326-2337. (b) Louie, J.; Hartwig, J. F. J. Am. Chem. Soc. 1995, 117, 11598-11599.
-
(1995)
J. Am. Chem. Soc.
, vol.117
, pp. 11598-11599
-
-
Louie, J.1
Hartwig, J.F.2
-
63
-
-
0012857368
-
-
The insertion of alkenes into Pd-C bonds in intramolecular Heck reactions occurs through a conformation in which the alkene π-bond and the Pd-C bond are eclipsed. The analogous insertion into the Pd-O bond via an eclipsed conformation is depicted in Figures 3 and 4. See: Link, J. T. Org. React. 2002, 60, 157-534.
-
(2002)
Org. React.
, vol.60
, pp. 157-534
-
-
Link, J.T.1
-
64
-
-
17444427428
-
-
note
-
Diastereoselectivities in related Pd(II)-catalyzed carbonylations of 1-substituted 4-penten-1-ols that proceed via a Wacker-type mechanism are typically in the range of 1-3:1. See ref 7a-d.
-
-
-
|