The use of radicals in organic synthesis has a rich history in the progression of chemical synthesis. In the early days, proving the very existence of radicals was an exciting area. Following that, their exploration in organic and organometallic chemistry led to a wellspring of useful discoveries. The classic studies of Stork, Curran, Barton, Zard, Minisci, 9, 10 and others showed how radicals could be tamed to make useful bonds. The modern manifestation of radical retrosynthesis has the potential to transform conventional logic and enable dramatically simplified routes to seemingly trivial and structures. It has now been demonstrated multiple times that such logic can obviate the need for otherwise arduous multistep synthetic sequences that are wedded to polar (2 electron) disconnections. Polar bond analysis, a useful rubric for synthesis planning, is often plagued by a reliance on protecting group chemistry, superfluous redox fluctuations and functional group manipulations that lower the ideality of a synthetic design. In contrast, radical-based transformations offer new disconnection opportunities that are often far more convergent, enabling access to an expanded chemical space. This is in part due to the higher chemoselectivity of single electron processes leading to a lower reliance on protecting groups. Such approaches have been highly impactful in the context of medicinal chemistry efforts, where expedient and modular access to a broad range of analogues is critical for exploring key biological hypotheses. For instance, the construction of potential drug candidates is often guided by the presence of C(sp 2 )-C(sp ) linkages, which are an essential motif in countless active pharmaceutical ingredients and are often a vector where SAR studies are performed with great diligence. Therefore, the development of synthetic methods that give access to a vast swath of chemical space by merging two accessible and benchtop-stable partners have attracted great attention. To this end, cross coupling partners such as carboxylic acids and aryl halides represent an attractive choice owing to their widespread commercial availability. For this reason, numerous radical decarboxylative cross coupling methodologies have been developed thereby opening up a more intuitive retrosynthesis of high-value targets. As an example, trivial looking unnatural amino acids like homotyrosine (Figure ), have historically been accessed through linear multistep syntheses using exclusively polar transformations that require careful reaction set up, preparation of organometallic reagents, multiple protecting group manipulations, and unstable intermediates that do not intuitively map onto the final target. Strikingly, these multistep routes, ranging from 5-10 steps, feature only one strategic bond forming step to forge a single C-C bond. Alternatively, using radical retrosynthesis, homotyrosine and other analogues could easily be traced back to glutamic acid and an appropriate aryl halide in a single step operation. To test the viability of this strategy, numerous decarboxylative cross coupling (DCC) methods that represent the current state of the art were tested (Figure ). First, cross electrophile coupling using zinc as a terminal reductant delivered only 9% of 1. Next, an electrochemical approach was pursued but no product formation with this challenging coupling partner 3 was observed. We next turned our attention towards photochemically enabled reactivity platforms. First, a reductive cross electrophile coupling leveraging electron donor acceptor complexes was evaluated. In the event, no desired product was formed. Finally, an oxidative activation of the carboxylic acid was evaluated, using photoinducedelectron transfer (PET, Ir-based) and a key phthalimide additive. However, even with this method, only no desired product was observed. At first glance, these results are surprising given the extensive body of literature around such transformations. However, upon closer examination of our desired cross coupling reaction and the surrounding literature, several key challenges were limiting the success of this coupling (Figure ). First, the scope of aryl electrophiles for C(sp 2 )-C(sp 3 ) reductive cross coupling generally favors electron deficient arenes and heterocycles over their electron rich counterparts even without considering sensitive functionality. Second, the carboxylic acid or corresponding redox active ester, if it is not engaged in productive catalysis, is prone to several decomposition pathways. These include H-atom abstraction by transient radicals, dimerization, and in the case of redox active esters, unproductive N-O bond heterolysis resulting in recovery of the acid starting material. In extreme cases, where the reaction does not proceed, only starting materials are recovered. In this Article a practical method to overcome the limitations of decarboxylative arylation is presented. It features a wide scope amongst challenging real-world substrates, extreme operational simplicity, and a versatile scale regime from parallel screening (mg) to recirculating flow scale up (decagram). Most importantly, the results herein are presented in context with existing methods for achieving the same transformation and conducted in collaboration with a diverse array of practitioners across five different pharmaceutical partners (the typical end user of this method).