Download Asymmetric functionalization of C-H bonds by Shu-Li You, Chris Hardacre PDF

By Shu-Li You, Chris Hardacre

Asymmetric C-H direct functionalization reactions are the most energetic and engaging components of analysis in natural chemistry as a result of their importance within the development of molecular complexity with no pre-activation, and the step financial system and atom economic climate good points in capability artificial software. Distinguishing the reactivity between a variety of C–H bonds in a single unmarried molecule represents essentially the most tough concerns in natural synthesis and calls for distinctive response layout. As such, this box is now receiving expanding cognizance from researchers.

This e-book presents the 1st finished assessment of this box, summarizing the starting place, mechanism, scope and purposes 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 by way of a number one professional during this box, the publication is perfect for postgraduates and researchers operating in natural synthesis, catalysis, and organometallic chemistry.

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Preliminary experiments showed that the reaction can be enantioselective. When using Ikegami’s dirhodium Rh2(S-PTPA)4 as the catalyst and NsNaIPh as the nitrene precursor,76 indane was transformed to the amidated product 98 with 7% ee. 34 The  first enantioselective CeH bond insertion reactions involving Rh nitrenoids reported by Müller. 35 Rh  II-catalyzed asymmetric CeH bond amination reactions reported by Hashimoto. enhanced to 31% ee. Although the results were not ideal, they opened the door to the advances in this specific area.

It is noteworthy that only methyl, ethyl, and cyclic methylene groups in the benzylic or allylic positions can be aminated. In addition, the amination product of aliphatic linear Z-olefin derivatives is not observed. Chapter 1 48 intramolecular amination reactions reported by Blakey. 10 Ru-catalyzed  Entry Solvent Additive Catalyst Yield (%) ee (%) 1 2 3 4 5 6 7 8 9 10a,b 11a,b 12a,b 13a,b 14a,c DCM Benzene Et2O DCM Benzene Et2O DCM Benzene Et2O DCM Benzene Et2O Benzene Benzene — — — AgOTf AgOTf AgOTf AgOTf AgOTf AgOTf AgOTf AgOTf AgOTf AgOTf AgOTf C14 C14 C14 C14 C14 C14 C15 C15 C15 C15 C15 C15 C16 C16 50 47 33 61 49 42 94 45 40 98 84 58 93 84 24 26 43 53 70 77 69 84 84 61 76 81 80 84 a  hI(CO2tBu)2 was used in place of PhI(OAc)2.

32 Fe-catalyzed  asymmetric CeH bond functionalization reactions of indoles reported by Zhou. 38 The elaborate screening of the reaction parameters unveiled that the combination of spiro bisoxazoline (S,S,Ra)-L3 as ligand and Fe(ClO4)2 as Fe precursor could give the optimal results (92% yield, 73% ee). The corresponding α-aryl-α-indolylacetates 94 were obtained in up to 94% yield and 78% ee, which could be readily purified by recrystallization in most cases. This study suggested a promising future for the application of sustainable and environmentally friendly catalysts in carbene transformations.

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