By Shu-Li You, Chris Hardacre
Asymmetric C-H direct functionalization reactions are the most lively and engaging components of study in natural chemistry as a result of their value within the development of molecular complexity with no pre-activation, and the step economic system and atom economic system beneficial properties in capability artificial program. Distinguishing the reactivity between quite a few C–H bonds in a single unmarried molecule represents probably the most not easy concerns in natural synthesis and calls for specific response layout. As such, this box is now receiving expanding realization from researchers.
This ebook presents the 1st complete overview of this box, summarizing the foundation, mechanism, scope and functions of the uneven C-H bond functionalization response. It covers organocatalytic reactions and transition-metal-catalyzed reactions, in addition to uneven C-H functionalization reactions no longer defined in different books.
Written through a number one specialist during this box, the ebook is perfect for postgraduates and researchers operating in natural synthesis, catalysis, and organometallic chemistry.
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The recent development achieved by Musaev, Davies, Blakey, and co-workers made the reactions more operative under ambient conditions without the demand for slow addition of the diazo ester or low temperature. Moreover, substituted 1,4-cyclohexadienes were also subjected to the reactions and the corresponding α,α-biarylacetates could be obtained in good yields (64–98%) with excellent enantioselectivity (90–99% ee) after the subsequent oxidation with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ).
Under these conditions, a series of five- and six-membered-ring products were obtained with up to 71% yield and 92% ee. 50). 48 Mn-catalyzed amination reactions reported by Katsuki. 49 Mn-catalyzed intramolecular amidation reactions reported by Che. corresponding six-membered ring product 136 was obtained and the aziridination product was not observed. 51). Under these conditions, a lot of substrates which contain benzylic or allylic CeH bonds were transformed to their corresponding aminated products with excellent enantioselectivity.
48, under the catalysis of C12, aminated indane compound 134 was produced in 63% yield and 66% ee by using PhIaNTs as the nitrene precursor. 49, top). To shed light on the rate-limiting step, competition experiments were performed with different groups on the arene core. 49, bottom). Meanwhile, it was suggested that this reaction is stereospecific as the enantiopure substrate gives the desired product with the identical absolute configuration. 102 Initially, the reaction was tested without any additives.
Asymmetric functionalization of C-H bonds by Shu-Li You, Chris Hardacre