1,4-Benzoquinone, BQ
1,4-Benzoquinone is a dehydrogenation reagent. The derivative 2,3-dichloro-5,6-dicyanobenzoquinone is a stronger oxidant.
Recent Literature
A Pd(PPh3)4-catalyzed reaction between α-diazocarbonyl
compounds and arylboronic acids leads to cross-coupled products in good yields.
C. Peng, Y. Wang, J. Wang, J. Am. Chem. Soc., 2008,
130, 1566-1567.
1,4-Benzoquinones have been found to prevent olefin isomerization of a number
of allylic ethers and long-chain aliphatic alkenes during ruthenium-catalyzed
olefin metathesis reactions. This mild, inexpensive, and effective method
increases the overall product yield and purity.
S. H. Hong, D. P. Sander, C. W. Lee, R. H. Grubbs, J. Am. Chem. Soc.,
2005,
127, 17160-17161.
A novel chelate-controlled intermolecular oxidative Heck reaction proceeds with
a wide range of nonresonance stabilized α-olefin substrates and organoboron
reagents to afford internal olefin products in good yields and outstanding
regio- and E:Z stereoselectivities. Pd-H isomerization, common in many
Heck reactions, is not observed under these mild, oxidative conditions.
J. H. Delcamp, A. P. Brucks, M. C. White, J. Am. Chem. Soc., 2008,
130, 11270-11271.
A Pd-catalyzed intermolecular 1,2-carboamination route to indolines from N-aryl
ureas and 1,3-dienes proceeds under mild conditions in relatively nonacidic
media via a C-H insertion/carbopalladation/nucleophilic displacement process.
The in situ generation, or preformation of a palladium tosylate emerges as a key
parameter in gaining the requisite reactivity.
C. E. Houlden, C. D. Bailey, J. G. Ford, M. R. Gagné, G. C. Lloyd-Jones, K. I.
Booker-Milburn, J. Am. Chem. Soc., 2008,
130, 10066-10067.
