Catalytic C-H activation has emerged in the past two decades as a powerful and sustainable tool in organic synthesis. However, the knowledge and the applicability of this chemistry has not yet reached its full potential. Ideally, to use C-H activation as a standard strategy in organic synthesis, chemists should be able to selectively activate a desired C-H bond. However, activation of a C-H bond further than the g-position from a directing group is still an under explored field.<br/>To achieve high selectivity, the use of directing groups is common. However, the use of this strategy leads to the activation of C-H bonds in proximity to the directing group. Another way to perform this activation is <i>via</i> through-space 1,4-metal migrations. Our group already has a longstanding experience in this subject, leading to a domino double C-H activation pathway with the first report of an allyl-to-allyl Rh(III) 1,4-migration (Scheme 1). Following our interest in C-H activation, we are working on expanding this methodology reaching the activation of further C-H bonds. In this poster we present a Rh(III)-catalyzed relay process that couples benzamides with skipped dienes that employs allyl-to-allyl 1,4-migration as a key step.

Rh(III)-catalyzed C-H activation by allyl-to-allyl 1,4-migration

256th National Meeting (2018)

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