The day may come when you must leave a relationship. Maybe "Branched N-1 Substituted Thymine Derivative" Bob just couldn't keep you happy :(
Have no fear! With these related papers, you can move far, far away from old loves while still keeping some of your old chemistry alive.
Zhang, X.; Yang, Z.; Huang, L.; You, S. Agnew. Chem. Int. Ed. 2015, 54, 1873-1876.
Building off of the work of Stanley and Hartwig, the You lab developed an intermolecular method of iridium-catalyzed amination of 2-hydroxopyridines. Amination may occur with a variety of functional groups and in extremely high yields.
Crabtree, R.H. Chemical Reviews 2015, 115, 127-150.
Crabtree, an extremely renown organometallics chemist, comments not on the potential uses of organometallic catalysts, but discusses the issue of premature catalyst deactivation in the context of existing reactions. Specifically, with certain functional groups researched by Hartwig, Iridium may be prone to deactivation and significantly slow the rate of reaction. Catalyst ratios may be adjusted to avoid many of these issues.
Arnold, J. S.; Mwenda, E. T.; Nguyen, H. M. Angewandte Chem. Int. Ed. 2014, 53, 3688-3692.
The authors develop a new application of Rhodium-catalyzed ring formation by introducing a variation of oxidative annulation in which 1,3-enynes may function as 1-carbon reaction partners rather than 2-carbon partners. This mechanistic variant of rhodium-catalyzed ring formation may be useful in expanding the utility of organometallic catalyzed reactions.
During the process of Batzelladine-D synthesis, the authors of our paper performed an allylic amination of 3,4-dihydropyrimidin-2(1H)-one to stereoselectively synthesize an amine from heterocyclic nitrogen. The authors described their starting reagent as a pro-nucleophile, and had little trouble creating the desired diastereomer in high yield (84%) with the use of catalytic Rhodium, trimethyl phosphite, and a lithium hydride analogue. However, generally speaking, the stereoselective amination of a heterocycle nitrogen may not always be easy, especially if the starting material cannot readily become nucleophilic. Stanley and Hartwig sought to explore more robust methods of heterocyclic amination that could perhaps be applied to less nucleophilic reagents. Rather than Rhodium, the authors developed an amination method using Iridium which produced stereospecific products in extremely high yield in many classes of starting material.In the most simplified sense, an iridium catalyst proved to be more reactive with less nucleophilic compounds due to a larger electron cloud and greater flexibility of the square-planar complex of the intermediate compared to rhodium. Additionally, Iridium-catalyzed conditions do not require the presence of exogenous base when aminating imidazoles or benzimidazoles.
Stanley, L.M. ; Hartwig, J.F. J. Am. Chem. Soc. 2009, 131, 8971-8983.
Enderlin, G.; Taillefumier, C.; Didierjean, C.; Chapleur, Y. J. Org. Chem. 2009, 74, 8388-8391.
Gharpure, S.J.; Niranjana, P. ; Porwal, S.K. Org. Lett. 2012, 14, 5476-5479.