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 28.06.2012   Карта сайта     Language По-русски По-английски
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Экология
Электротехника и обработка материалов
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28.06.2012

Activation of remote meta-C–H bonds assisted by an end-on template





Journal name:

Nature

Volume:

486,

Pages:

518–522

Date published:

(28 June 2012)

DOI:

doi:10.1038/nature11158


Received


Accepted


Published online







Functionalization of unactivated carbon–hydrogen (C–H) single bonds is an efficient strategy for rapid generation of complex molecules from simpler ones. However, it is difficult to achieve selectivity when multiple inequivalent C–H bonds are present in the target molecule. The usual approach is to use σ-chelating directing groups, which lead to…





Figures at a glance


left


  1. Figure 1: A template strategy for the activation of distal meta-C–H bonds (more than ten bonds away).
    A template strategy for the activation of distal meta-C-H bonds (more than ten bonds away).

    a, Remote meta-C–H activation is a challenge. I: ortho-directed C–H activation. DG, directing group. II, III and IV: Remote meta-C–H activation using an ‘end-on’ template. The dotted blue lines divide the arene template into four quadrants. The blue bonds in all figures highlight the targeted C–H bonds. b, Templates for toluenes and hydrocinnamic acids. c, Unprecedented positional selectivity in C–H activation, overriding electronic and steric biases, and ortho-directing effects.. d, Structurally related drug molecules (brand names in parentheses).




  2. Figure 2: Template-directed meta-selective C–H olefination of toluene derivatives.
    Template-directed meta-selective C-H olefination of toluene derivatives.

    a, Arenes (8ap) with a variety of substitution patterns undergo facile olefination. b, In the box, many election-deficient olefins and various di- and tri-substituted olefins were used. The isolated yield of the mono-olefinated product (and also the isolated yield of the di-olefinated product when applicable) is shown along with the selectivity. See Supplementary Information for experimental details. Selectivity of the mono- and di-olefinated products was determined by 1H NMR analysis and confirmed by one-dimensional selective NOESY experiments; the variance is estimated to be within 5%. OPiv, pivalate.




  3. Figure 3: Template-directed meta-selective C–H olefination of hydrocinnamic acid derivatives.
    Template-directed meta-selective C-H olefination of hydrocinnamic acid derivatives.


 


 


 


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