I just felt like sharing something I read today
The book is Palladium Reagents and Catalysts, Innovations in Organic Synthesis by Jiro Tsuji
So here's a quick fact list with their references. I havent looked into any of them yet but maybe some of you will feel like looking too. Of course some stuff might be known to most of you, I didnt feel like UTFSE , anyway I dont have any questions about it...yet
Taken from page 22-24
Refering to CuCl2/O2 system
- DMF is widely used as a solvent, but the oxidation proceeds faster in alcohols. Double bond isomerisation occurs extensively in alcohols1
- Polyethylene glycol(PEG 400) is a good solvent for the oxidation of terminal and internal alkenes 2
- Sometimes, chlorination of carbonyl compounds is observed with the use of CuCl2. The use of CuCl, after facile preoxidation to Cu 2+ with oxygen, is recommended because no chlorination takes place with CuCl3,4,5
- FeCl3, HNO3 and MnO2 can oxidize Pd(0), but stochiometric amounts are necessary. (unfortunately they dont mention anything else, no ref)
- Benzoquinone is most widely used. The oxidation can be carried out using a catalytic amount of benzoquinone by the combination of electrochemical oxidation as shown6
The drawing shows hydroquinone being reoxidized to benzoquinone at the anode.
Tetrahedron Lett. and Journal of Organic chem are classics,easy to get, I wonder if I'll find anything really interesting.
1. D.G. Lloyd and B.J. Luberoff, J. Org. Chem., 34, 3949(1969)
2. H. Alper, K.Januzkiewicz, and D.J. H. Smith, Tetrahedron Lett., 26, 2263(1985)
3. J.Tsuji, I. Shimizu, and K.Yamamoto, Tetrahedron Lett., 2975(1976)
4. J.Tsuji, I. Shimizu, and Y.Kobayashi, Isr. J. Chem, 24, 153(1984)
5. F.J. McQuilin and D.G. Parker, J. Chem. Soc., Perkin Trans. 1, 809(1974)
6. J. Tsuji and M.Minato, Tetrahedron Lett., 28,3683(1987)
