By Alexandre Alexakis, Norbert Krause, Simon Woodward
This ebook displays the expanding curiosity one of the chemical artificial neighborhood within the quarter of uneven copper-catalyzed reactions, and introduces readers to the newest, most important advancements within the field.
The contents are prepared based on response kind and canopy mechanistic and spectroscopic elements in addition to purposes within the synthesis of typical items. a complete bankruptcy is dedicated to knowing how fundamental organometallics have interaction with copper to supply selective catalysts for allylic substitution and conjugate addition, either one of that are taken care of in separate chapters. one other is dedicated to the diversity of substrates and experimental protocols, whereas a whole bankruptcy covers the use on non-carbon nucleophiles. different chapters care for less-known reactions, comparable to carbometallation or the additions to imines and comparable structures, whereas the extra demonstrated reactions cyclopropanation and aziridination in addition to using copper (II) Lewis acids are warranted their very own specific chapters. additional chapters predicament the procedures concerned, as made up our minds by means of mechanistic reviews. ultimately, an entire bankruptcy is dedicated to the bogus applications.
this is often crucial studying for researchers at educational associations and execs at pharmaceutical or agrochemical businesses.
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Extra info for Copper-Catalyzed Asymmetric Synthesis
One other common scenario is use of a chiral Lewis acid fragment linked to a simple heterocuprate via a bridging ligand 3. 1 Generalized binding modes for Cu-promoted activation of prochiral substrates where MR is a main group organometallic, X is a halogen, D is a generalized two electron donor, and “bridge” is a generalized anionic ligand. ) is, of course, possible. Clearly, in attaining enantioselective transition states for asymmetric reactions, the nature of the bridging ligand (typically a halide or pseudohalide) is at least as important as the identification of an effective chiral ligand ( L*) in attaining effective docking of substrates in 1–3.
Support for these ideas comes from the interaction of theory and experiment. Replacing the CuMe2− fragment by MeCuCN− in the DFT modeled oxidative addition reveals two factors: (i) a slower oxidative addition, but (ii) high polarization of the Cu dxz-based highest occupied molecular orbital (HOMO) providing greater electron density trans to the CN group. This leads to more developed Cγ–Cu bond in transition state 11, which is retained in the resulting Me(CN)CuIII (allyl) intermediate (the analog of 10).
DFT modeling of this proposed pathway suggests that the rate determining step for the process is transmetallation of copper alkoxide intermediate. The absence of any nonlinear effect (NLE) in the product ee when scalemic mixtures of a chiral ligand are used point strongly to mononuclear catalysis. 5. The half dependence in catalyst concentration is believed to indicate that the resting state of the catalyst is the copper dimer 54 . Very recently an example (2011, structure INIRIH) of such a species has been characterized where the bridging hydrides were crystallographically located .
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