The development of transition metal-catalyzed crosscoupling reactions ushered in a new era of retrosynthetic disconnections that subsequently changed the way medicinal chemists design and synthesize molecules. At first, enabling C(sp 2 )-C(sp 2 ) and C(sp 2 )-C(sp) bond formation in a robust and reliable way set the stage for modern diversification strategies and led to a rapid expansion of the medicinal chemistry toolkit. The development of this versatile platform witnessed an exponential growth after the 1990s both in terms of publications and patents, until it reached its peak after 2010. Nowadays, the construction of C-C bonds via Suzuki, Negishi, 4 Kumada, Stille, Sonogashira, and Heck 8 couplings is considered intuitive and logical. As a result, the problem of crafting C(sp 2 )-C(sp 2 ) and C(sp 2 )-C(sp) linkages is perceived as largely solved (Figure ). On the other hand, the logical extension of this concept to C(sp 2 )-C(sp ) bond formation has remained underdeveloped. The use of alkyl organometallic reagents in the context of Pd-catalyzed cross-couplings is not as general as their aryl/alkenyl counterparts, as many concerns arise on the stability of the requisite alkyl organometallic reagents, chemoselectivity issues, and the challenge of β-hydride elimination that can affect the outcome of such catalytic transformations. This limitation represents a striking opportunity for innovation within the landscape of molecular design, due to ubiquitous presence of aryl/alkyl or alkenyl/alkyl bonds in Nature as well as pharmaceutical or agrochemical compounds. Decades of research on canonical polar approaches for C(sp 2 )-C(sp 3 ) cross-coupling have iterated on the lessons learned in classic Suzuki, Kumada, and Negishi couplings. Despite extensive modifications of conditions and ligands to effect such transformations, a robust strategy to enable a level of diversification akin to the (sp 2 )-C(sp 2 ) and C(sp 2 )-C(sp) ones remains elusive. From first principles, even a fully optimized variant of such chemistry would require the synthesis of bespoke alkyl-M fragments which is not ideal for a medicinal chemistry campaign (Figure ). Over the last decade the community has begun to embrace a different retrosynthetic logic that departs from polar-bond analysis and instead makes polarity-agnostic convergent disconnections resulting in radical synthons. Radical retrosynthesis relies on the use of convenient precursors (often ubiquitous) to expand the selection of coupling partners. The pioneering work of Kochi, and Morrell, 11 also provided the basis for using transition metals other than palladium thereby mitigating the problem of βhydride elimination. 12 Among the wide array of radical-based, transition metal-catalyzed cross-coupling reactions, the decarboxylative cross-coupling (DCC) approach is perhaps most appealing, as carboxylic acids are widely commercially available (more so than any other functional group), benchtop stable and amenable to multiple modes of functionalization. Not surprisingly, numerous publications have been released on this topic in the last decade, with a similar scenario emerging to canonical cross-coupling during the 90s (Figure ).