Boronic acids are amongst the most useful synthetic intermediates, frequently used by modern drug design. However, their access and fast synthesis of libraries are often problematic. We present a methodology on the synthesis of drug-like scaffolds via IMCRs with unprotected phenylboronic acids. To demonstrate an application of our approach, we also performed one-pot Suzuki couplings on the primary MCR scaffolds. Moreover, we performed a thorough data-mining of the Cambridge Structural Database, revealing interesting geometrical features.