Thousands of variants of these two-electron, polar reaction types have been reported thereby forming the bedrock of the logic of retrosynthetic analysis. Designing a route to complex structures using these methods can often involve a complex interplay of stereo-, regio-, and chemoselectivty considerations along with balancing proper redox states. As such, vast realms of protecting groups, reagents, and stereochemical rubrics have been developed to aid the practitioner in executing synthetic plans. Years of experience is necessary to appropriately deploy various reactions with successful synthetic strategies often being considered a form of "art". Numerous computerbased algorithms and software packages have been launched to simplify synthesis design which is often equated with providing solutions to a complex puzzle. In contrast, a different approach to retrosynthesis that uses radical-based logic (1e - disconnection) to create new C-C bonds is emerging that can directly access previously challenging motifs, and in the process avoid downstream functional/protecting group manipulations and extraneous redox fluctuations. Since disconnections based on radical retrosynthesis are polarity agnostic, any C-C bond can, in principle, be constructed by the coupling of carbon radicals regardless of the surrounding functional groups. This, in turn, opens up completely different ways of making molecules since polarity assignments do not need to be the sole criteria to guide a logical disconnection. Instead, maximization of convergency and starting material availability/simplicity can serve as a primary guiding principle. Towards this end, doubly decarboxylative cross coupling (dDCC) is a powerful tool to realize this vision as it directly forges Csp 3 -Csp 3 bonds between two carboxylic acids. Whereas the initial manifestation of this chemistry did not tolerate adjacent functional groups, herein we disclose a method to extend the scope of this reaction enabling the modular coupling of α-functionalized acids to access structures classically associated with 2e -synthetic strategies (Figure ).