Novel highly regioselective VO (acac) 2/TBHP mediated oxidation of o-alkenyl phenols to o-hydroxybenzyl ketones

A Lattanzi, A Senatore, A Massa…

Index: Lattanzi, Alessandra; Senatore, Antonello; Massa, Antonio; Scettri, Arrigo Journal of Organic Chemistry, 2003 , vol. 68, # 9 p. 3691 - 3694

Full Text: HTML

Citation Number: 39

Abstract

A novel mild methodology for the preparation of o-hydroxybenzyl ketones is described starting from o-alkenyl phenols and based on the VO (acac) 2/TBHP (2 mol%/1.2 equiv) system. VO (acac) 2 first catalyzes the epoxidation of o-alkenyl phenols and then the rearrangement of the epoxyphenols to ketones via the selective benzylic CO cleavage and 1, 2 hydride migration. The protocol has also been applied to set up a useful and easy one ...

Related Articles:

Palladium-Catalyzed Selective Heck-Type Diarylation of Allylic Esters with Aryl Halides Involving a β-OAc Elimination Process

[Liu, Yan; Yao, Bo; Deng, Chen-Liang; Tang, Ri-Yuan; Zhang, Xing-Guo; Li, Jin-Heng Organic Letters, 2011 , vol. 13, # 5 p. 1126 - 1129]

Ruthenium NHC catalyzed highly asymmetric hydrogenation of benzofurans

[Ortega, Nuria; Urban, Slawomir; Beiring, Bernhard; Glorius, Frank Angewandte Chemie - International Edition, 2012 , vol. 51, # 7 p. 1710 - 1713]

Chromium (II) salt mediated reductive transposition of an ester acyl group in ortho-O-acyl benzylic bromides: a ready access to unmasked ortho-hydroxybenzyl …

[Ledoussal, Benoit; Gorgues, Alain; Coq, Andre Le Journal of the Chemical Society, Chemical Communications, 1986 , # 2 p. 171 - 172]

Palladium-Catalyzed Selective Heck-Type Diarylation of Allylic Esters with Aryl Halides Involving a β-OAc Elimination Process

[Liu, Yan; Yao, Bo; Deng, Chen-Liang; Tang, Ri-Yuan; Zhang, Xing-Guo; Li, Jin-Heng Organic Letters, 2011 , vol. 13, # 5 p. 1126 - 1129]

Revisit to the reduction of allylic chlorides to less substituted olefins by a low-valent chromium species in the presence of a proton source

[Omoto, Mineko; Kato, Nobuo; Sogon, Tetsuya; Mori, Akira Tetrahedron Letters, 2001 , vol. 42, # 5 p. 939 - 941]

More Articles...