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A preeminent challenge in alkene difunctionalization is the control of regio-, diastereo-, and enantioselectivity. In this Perspective, a Pd/Cu-cooperative catalytic system for alkene arylboration is highlighted that allows for the controlled introduction of substituents. In particular, examples that allowed for divergent reactivity from a single substrate based on the tuning of catalysts and reaction conditions are emphasized.

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A rhodium-catalyzed cross-coupling of aryl and aliphatic quinolinyl ketones with boronic acids has been developed. Proceeding via quinoline-directed carbon-carbon σ bond activation, the transformation demonstrates tolerance of a range of functional groups on both the ketone and aryl boronic acid substrates, providing good to excellent yields of the new ketones, particularly those containing electron-withdrawing substituents. Catalyst reactivity is dependent on quinolinyl ketone substrates, with alkyl ketones requiring Rh(PPh3)3Cl instead of the more reactive [Rh(C2H4)2Cl]2. With the use of K2CO3 as an additive, methyl boronic acid is also a competent substrate, giving rise to an unprecedented methylation technique.

We have developed a course-based undergraduate research experience (CURE) that can be carried out in the context of an existing second-semester or upper-level organic laboratory course. In this three-week laboratory module, students synthesize a small library of molecules, test them in a robust biological assay, and design a new compound library on the basis of their results.