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The C–H borylation of indolizines has not previously been reported. In this communication, we describe our preliminary efforts to apply this chemistry to this scaffold and contrast this approach to directed metalation. Through these methodologies, it was possible obtain a library of substituted indolizines functionalized on both the pyridinic and pyrrole rings.

The full-text may be used and/or reproduced, and given to third parties in any format or medium, without prior permission or charge, for personal research or study, educational, or not-for-prot purposes provided that:• a full bibliographic reference is made to the original source • a link is made to the metadata record in DRO • the full-text is not changed in any way The full-text must not be sold in any format or medium without the formal permission of the copyright holders.

Borylation. -In the absence of any steric directing group, the title reaction proceeds selectively at C-3 of the indazole skeleton. The borylated site can be used for various further functionalizations as is demonstrated for some examples. The additional presence of a bromide substituent allows further transformations. Diborylated indazoles formed by treatment of the substrate [cf. (X)] with 2 equiv. of (II) are not suitable for selective coupling: in situ protodeborylation at C-3 produces the boronate ester at C-5, which can be arylated. -(SADLER, S. A.; HONES, A. C.; ROBERTS, B.; BLAKEMORE, D.; MARDER, T. B.; STEEL*, P. G.; J. Org. Chem. 80 (2015) 10, 5308-5314, http://dx.