-
4
-
-
33845281119
-
Electrophiles used in palladium-catalyzed condensation reactionslb,c include acyl chlorides, allyl halides, vinyl halides and triflates, aryl halides and triflates, vinyl epoxides and perfluoroalkyl iodides
-
Aryl halides
-
Electrophiles used in palladium-catalyzed condensation reactionslb,c include acyl chlorides, allyl halides, vinyl halides and triflates, aryl halides and triflates, vinyl epoxides and perfluoroalkyl iodides. For very recent references, see the following. Vinyl halides: (a) Stille, J. K.; Groh, B. L. J. Am. Chem. Soc. 1987,109, 813. Aryl halides:
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J. Am. Chem. Soc.
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Stille, J.K.1
Groh, B.L.2
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5
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McKean, D. R.; Parinello, G.; Renaldo, A. F.; Stille, J. K. J. Org. Chem. 1987,52, 422.
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McKean, D.R.1
Parinello, G.2
Renaldo, A.F.3
Stille, J.K.4
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6
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45549111739
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Haack, R. A.; Penning, T. D.; Djuric, S. W.; Dziuba, J. A. Tetrahedron Lett. 1988, 29,2783.
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Tetrahedron Lett.
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, pp. 2783
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Haack, R.A.1
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Djuric, S.W.3
Dziuba, J.A.4
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12
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0023889587
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Krolski, M. E.; Renaldo, A. F.; Rudisil, D. E.; Stille, J. K. J. Org. Chem. 1988, 53, 1170.
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Krolski, M.E.1
Renaldo, A.F.2
Rudisil, D.E.3
Stille, J.K.4
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13
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0000380193
-
Vinyl epoxides
-
Vinyl epoxides: (j) Echavarren, A. M.; Tueting, D. R.; Stille, J. K. J. Am. Chem. Soc. 1986, 110, 4039. Allyl halides:
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(1986)
J. Am. Chem. Soc.
, vol.110
, pp. 4039
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Echavarren, A.M.1
Tueting, D.R.2
Stille, J.K.3
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16
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0000977041
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Matsubara, S.; Mitani, M.; Utimoto, K. Tetrahedron Lett. 1987, 28, 5857.
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Tetrahedron Lett.
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Matsubara, S.1
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Utimoto, K.3
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17
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0000404899
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Behling, J. R.; Babiak, K. A.; Ng, J. S.; Campbell, A. L.; Moretti, R.; Koerner, M.; Lipshutz, H. B. J. Am. Chem. Soc. 1988, 110, 2641.
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Behling, J.R.1
Babiak, K.A.2
Ng, J.S.3
Campbell, A.L.4
Moretti, R.5
Koerner, M.6
Lipshutz, H.B.7
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18
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0002899916
-
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Wulff, W. D.; Peterson, G. A.; Bauta, E. W.; Chan, K. S.; Faron, K. L.; Gilbertson, S. R.; Kaesler, R. W.; Yang, D. C.; Murray, C. K. J. Org. Chem. 1986, 51, 277 and references therein.
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Wulff, W.D.1
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Chan, K.S.4
Faron, K.L.5
Gilbertson, S.R.6
Kaesler, R.W.7
Yang, D.C.8
Murray, C.K.9
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19
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37049100645
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Baldwin, J. E.; Kelly, D. R.; Ziegler, C. B. J. Chem. Soc., Chem. Commun. 1984,133.
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Baldwin, J.E.1
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Ghozal, S.; Luke, J. P.; Kyler, K. S. J. Org. Chem. 1987, 52, 4296.
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23
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0001438331
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Leusink, A. J.; Budding, H. A.; Drenth, W. J. Organomet. Chem. 1968, 11, 541 and references therein.
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Nozaki, K.; Oshima, K.; Utimoto, K. J. Am. Chem. Soc. 1987, 109, 2547.
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37
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0000672350
-
After this work was well underway, two short communications appeared dealing, respectively, with palladium-catalyzed and with rhodium-catalyzed hydrostannation reactions
-
After this work was well underway, two short communications appeared dealing, respectively, with palladium-catalyzed and with rhodium-catalyzed hydrostannation reactions: Ichinose, Y.; Oda, H.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1987, 60, 3468.
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Bull. Chem. Soc. Jpn.
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Ichinose, Y.1
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85023867503
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For very recent references, see the following
-
Electrophiles used in palladium-catalyzed condensation reac-tions1b,c include acyl chlorides, allyl halides, vinyl halides and triflates, aryl halides and triflates, vinyl epoxides and perfluoroalkyl iodides. For very recent references, see the following.
-
Electrophiles used in palladium-catalyzed condensation reac-tions1b,c include acyl chlorides, allyl halides, vinyl halides and triflates, aryl halides and triflates, vinyl epoxides and perfluoroalkyl iodides
-
-
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44
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0346184325
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McKean, D.R.; Parinello, G.; Renaldo, A. F.; Stille, J. K. J. Org. Chem. 1987, 52, 422.
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(1987)
J. Org. Chem.
, vol.52
, Issue.422
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McKean, D.R.1
Parinello, G.2
Renaldo, A.F.3
Stille, J.K.4
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45549111739
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Haack, R. A.; Penning, T. D.; Djuric, S. W.; Dziuba, J. A. Tetrahedron Lett. 1988,29, 2783.
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(1988)
Tetrahedron Lett.
, vol.29
, pp. 2783
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Haack, R.A.1
Penning, T.D.2
Djuric, S.W.3
Dziuba, J.A.4
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51
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0023889587
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Krolski, M. E.; Renaldo, A. F.; Rudisil, D. E.; Stille, J. K. J. Org. Chem. 1988, 53, 1170.
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(1988)
J. Org. Chem.
, vol.53
, pp. 1170
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Krolski, M.E.1
Renaldo, A.F.2
Rudisil, D.E.3
Stille, J.K.4
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52
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0000380193
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Vinyl epoxides: Echavarren, A. M.; Tueting, D. R.; Stille, J. K. J. Am. Chem. Soc. 1986, 110, 4039.
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(1986)
J. Am. Chem. Soc.
, vol.110
, pp. 4039
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Echavarren, A.M.1
Tueting, D.R.2
Stille, J.K.3
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0000977041
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Perfluoroalkyl iodides: Matsubara, S.; Mitani, M.; Utimoto, K. Tetrahedron Lett. 1987, 28, 5857.
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Tetrahedron Lett.
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Behling, J. R.; Babiak, K. A.; Ng, J. S.; Campbell, A. L.; Moretti, R.; Koerner, M.; Lipshutz, H. B. J. Am. Chem. Soc. 1988, 110, 2641.
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(1988)
J. Am. Chem. Soc.
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Behling, J.R.1
Babiak, K.A.2
Ng, J.S.3
Campbell, A.L.4
Moretti, R.5
Koerner, M.6
Lipshutz, H.B.7
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57
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0002899916
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references therein
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Wulff, W. D.; Peterson, G. A.; Bauta, E. W.; Chan, K. S.; Faron, K. L.; Gilbertson, S. R.; Kaesler, R. W.; Yang, D. C.; Murray, C. K. J. Org. Chem. 1986, 51, 277 and references therein.
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Faron, K.L.5
Gilbertson, S.R.6
Kaesler, R.W.7
Yang, D.C.8
Murray, C.K.9
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37049100645
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Baldwin, J. E.; Kelly, D. R.; Ziegler, C. B. J. Chem. Soc., Chem. Commun. 1984,133.
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33845281114
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62
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85023834574
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In the absence of acetylenic compounds, an orange solution of 3 in THF under argon atmosphere immediately turns black and cloudy upon addition of Bu3SnH
-
The tin byproduct of the reaction is Bu3SnBr (GC/MS). IR analysis (after dilution in CHCI3) shows a single strong CO absorption at 1950 cm-1. Thus, the species which forms is not the known (THF)3Mo(CO)3 (kc0 = 1920 and 1780 cm1. Hoff, C. D. J. Organomet. Chem. 1985, 282, 201). If the reaction of 3 and Bu3SnH is performed under CO atmosphere (in this case the solution turns red and stays homogeneous), the CO band at 1950 cm-1 is progressively replaced, over ca. 1 h, by the CO band at 1986 cm-1 of Mo(CO)6, which can be precipitated out of the solution quantitatively
-
In the absence of acetylenic compounds, an orange solution of 3 in THF under argon atmosphere immediately turns black and cloudy upon addition of Bu3SnH. NMR analysis (THF-d6) shows a complete disappearance of the proton signals20 of the 03BC-allyl entity. The tin byproduct of the reaction is Bu3SnBr (GC/MS). IR analysis (after dilution in CHCI3) shows a single strong CO absorption at 1950 cm-1. Thus, the species which forms is not the known (THF)3Mo(CO)3 (kc0 = 1920 and 1780 cm1. Hoff, C. D. J. Organomet. Chem. 1985, 282, 201). If the reaction of 3 and Bu3SnH is performed under CO atmosphere (in this case the solution turns red and stays homogeneous), the CO band at 1950 cm-1 is progressively replaced, over ca. 1 h, by the CO band at 1986 cm-1 of Mo(CO)6, which can be precipitated out of the solution quantitatively.
-
NMR analysis (THF-d6) shows a complete disappearance of the proton signals20 of the 03BC-allyl entity
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The values of the ligand cone angle 6 for P(o-tolyl)3, PPh3, and P(OMe)3 are, respectively, 194
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Simple bromoalkenes are not as reactive. For instance, under similar conditions and due to competitive tributyltin hydride decomposition, 1-bromostyrene is reduced only to the extent of ca
-
Simple bromoalkenes are not as reactive. For instance, under similar conditions and due to competitive tributyltin hydride decomposition, 1-bromostyrene is reduced only to the extent of ca. 50% by addition of one equivalent of tributyltin hydride (observations from this laboratory).
-
50% by addition of one equivalent of tributyltin hydride (observations from this laboratory)
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See also: Doyle, M. P.; Taunton, J.; Su-Min oon Liu, M. T. H.; Soundararajan, N.; Platz, M. S.; Jackson, J. E. Tetrahedron Lett. 1988, 9, 5863.
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