Categories: C-C Bond Formation > Nitrogen-containing molecules >
Synthesis of Nitriles
An efficient cobalt-catalyzed reductive coupling reaction of alkyl halides with alkenes bearing electron-withdrawing groups in the presence of water and zinc powder in acetonitrile gave the corresponding Michael-type addition products in high yields. The mechanism is discussed.
P. Shukla, Y.-C. Hsu, C.-H. Cheng, J. Org. Chem., 2006, 71, 655-658.
The simple and inexpensive combination of TiCl4(2,4,6-collidine) and manganese powder afforded a low-valent titanium reagent, which facilitated homolytic cleavage of benzylic C-OH bonds. Radical conjugate addition reactions of various benzyl alcohol derivatives with electron-deficient alkenes furnished the corresponding adducts in good yields.
T. Suga, S. Shimazu, Y. Ukaji, Org. Lett., 2018, 20, 5389-5392.
When used with photocatalysis, bench-stable, commercially available collidinium salts are excellent radical precursors with a broad scope, that can substitute alkyl halides. Furthermore, all of the reaction components are water-soluble, which facilitates product isolation.
M. D. Rathnayake, J. D. Weaver III, Org. Lett., 2021, 23, 2036-2041.
The ionic liquid [bmIm]OH is a catalyst and a reaction medium for Michael additions. Although the addition to α,β-unsaturated ketones gives the monoaddition products, this ionic liquid always drives the reaction of open-chain 1,3-dicarbonyl compounds with α,β-unsaturated esters and nitriles toward bis-addition.
B. C. Ranu, S. Banerjee, Org. Lett., 2005, 7, 3049-3052.