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2
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13244279541
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Intramolecular hydroalkoxylation of olefins: (a) Grant, V. H.; Liu, B. Tetrahedron Lett. 2005, 46, 1237-1239.
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Grant, V.H.1
Liu, B.2
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4
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27144523211
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(c) Yang, C-G.; Reich, N. W.; Shi, Z.; He, C. Org. Lett. 2005, 7, 4553-4556.
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Org. Lett.
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Yang, C.-G.1
Reich, N.W.2
Shi, Z.3
He, C.4
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8
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3543083464
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Qian, H.; Han, X.; Widenhoefer, R. A. J. Am. Chem. Soc. 2004, 126, 9536-9537.
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J. Am. Chem. Soc.
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Qian, H.1
Han, X.2
Widenhoefer, R.A.3
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10
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15444376499
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Hydroalkoxylation with Pd(0): Matsukawa, Y.; Mizukado, J.; Quan, H.; Tamura, M.; Sekiya, A. Angew. Chem., Int. Ed. 2005, 44, 1128-1130.
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Angew. Chem., Int. Ed.
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Matsukawa, Y.1
Mizukado, J.2
Quan, H.3
Tamura, M.4
Sekiya, A.5
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11
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4143153074
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For reviews of Pd-catalyzed oxidation reactions, see: (a) Stahl, S. S. Angew. Chem., Int. Ed. 2004, 43, 3400-3420.
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Angew. Chem., Int. Ed.
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Stahl, S.S.1
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14
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26844513781
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(b) For a similar example, see: Chevrin, C.; Bras, J. L.; Hénin, F.; Muzart, J. Synthesis 2005, 2615-2618.
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Synthesis
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Chevrin, C.1
Bras, J.L.2
Hénin, F.3
Muzart, J.4
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15
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27144547160
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and references therein
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2 in alcohol oxidations, see: Mueller, J. A.; Cowell, A.; Chandler, B. D.; Sigman, M. S. J. Am. Chem. Soc. 2005, 127, 14817-14824 and references therein.
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Mueller, J.A.1
Cowell, A.2
Chandler, B.D.3
Sigman, M.S.4
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16
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33644948817
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note
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See Supporting Information for details.
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-
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17
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33644966670
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note
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(a) One possibility to account for the formation of ketone is via acetal formation, which is hydrolyzed upon workup; for a review see ref 6b.
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18
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0034697701
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(b) Another possible pathway is via a Pd-catalyzed aerobic alcohol oxidation coupled Wacker oxidation. See: Nishimura, T.; Kakiuchi, N.; Onoue, T.; Ohe, K.; Uemura, S. J. Chem. Soc., Perkin Trans. 1 2000, 1915-1918.
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J. Chem. Soc., Perkin Trans. 1
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Nishimura, T.1
Kakiuchi, N.2
Onoue, T.3
Ohe, K.4
Uemura, S.5
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19
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0000300355
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For an example of a nucleopalladation with a chiral secondary alcohol, see: Hosokawa, T.; Ohta, T.; Kanayama, S.; Murahashi, S.-I. J. Org. Chem. 1987, 52, 1758-1764.
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J. Org. Chem.
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Hosokawa, T.1
Ohta, T.2
Kanayama, S.3
Murahashi, S.-I.4
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20
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33644943592
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note
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Under identical conditions with 4-methylstyrene in ethanol, the Markovnikov diethyl acetal is formed.
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21
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33644941202
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note
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Only one deuterium atom is incorporated into the olefin, indicating that the equilibration of D and E does not include dissociation of the olefin.
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-
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22
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33947293332
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For an example of a stoichiometric Pd(II)-mediated formation of a quinone methide, see: Chapman, O. L.; Engel, M. R.; Springer, J. P.; Clardy, J. C. J. Am. Chem. Soc. 1971, 93, 6696-6698.
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J. Am. Chem. Soc.
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Chapman, O.L.1
Engel, M.R.2
Springer, J.P.3
Clardy, J.C.4
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