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1. π-Bond Dissociation Energies: C–C, C–N, and C–O

   https://doi.org/10.1021/acs.joc.4c01925  

   Kass, Steven R (October 2024, The Journal of Organic Chemistry)
2. Automated Iterative N─C and C─C Bond Formation

   https://doi.org/10.1002/anie.202509974  

   Tyrikos‐Ergas, Theodore; Agiakloglou, Sevasti; LaPorte, Antonio J; Wang, Wesley; Chan, Chieh‐Kai; Wells, Clare E; Rakowski, Christopher K; Hammond, Rachel I; Qiu, Jia; Raymond, Jonathan D; et al (August 2025, Angewandte Chemie International Edition)

   Small molecule solutions to many contemporary societal challenges await discovery, but the artisanal and manual process via which this class of chemical matter is typically accessed limits the discovery of new functions. Automated assembly of (N‐methyl iminodiacetic acid) MIDA or (tetramethyl N‐methyl iminodiacetic acid) TIDA boronate building blocks via iterative C─C bond formation, an approach we call “block chemistry”, alternatively enables generalized and automated preparation of many different types of small molecules in a modular fashion. But in its current form, this engine cannot also leverage nitrogen atoms as iteration handles. Here, we disclose a new iteration‐enabling group, CbzT (p‐TIDA boronate‐substituted carboxybenzyl), that reversibly attenuates the reactivity of nitrogen atoms and enables generalized catch‐and‐release purification. CbzT is leveraged to achieve the automated modular synthesis of Imatinib (Gleevec), an archetypical clinically approved kinase inhibitor, in which building blocks are iteratively linked by both N─C and C─C bonds. This work substantially expands the types of small molecules that can be iteratively assembled in an automated modular fashion. It also advances the concept of intentionally developing chemistry that machines can do. 

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3. Radical Capture at Nickel(II) Complexes: C–C, C–N, and C–O Bond Formation

   https://doi.org/10.1021/acs.organomet.0c00021  

   Bakhoda, Abolghasem Gus; Wiese, Stefan; Greene, Christine; Figula, Bryan C.; Bertke, Jeffery A.; Warren, Timothy H. (May 2020, Organometallics)

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4. C–C Cleavage Approach to C–H Functionalization of Saturated Aza-Cycles

   https://doi.org/10.1021/acscatal.9b04551  

   Roque, Jose B.; Kuroda, Yusuke; Jurczyk, Justin; Xu, Li-Ping; Ham, Jin Su; Göttemann, Lucas T.; Roberts, Charis A.; Adpressa, Donovon; Saurí, Josep; Joyce, Leo A.; et al (March 2020, ACS Catalysis)
5. x86-64 instruction usage among C/C++ applications

   https://doi.org/10.1145/3319647.3325833  

   Akshintala, Amogh; Jain, Bhushan; Tsai, Chia-Che; Ferdman, Michael; Porter, Donald E. (June 2019, Proceedings of the 12th ACM International Systems and Storage Conference)

   This paper presents a study of x86-64 instruction usage across 9,337 C/C++ applications and libraries in the Ubuntu16.04 GNU/Linux distribution. We present metrics for reasoning about the relative importance of instructions weighted by the popularity of applications that contain them. From this data, we systematize and empirically ground conventional wisdom regarding the relative importance of various components of an ISA, with particular focus on building binary translation tools. We also verify the representativity of two commonly used benchmark suites, and highlight areas for improvement. 

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