Continuous Flow Electroselenocyclization of Allylamides and Unsaturated Oximes to Selenofunctionalized Oxazolines and Isoxazolines

24h Integrating Electrochemical and Statistical Analysis Tools for Molecular Design and Mechanistic Understanding Robinson, Sophia G.; Sigman, Matthew S. Accounts of Chemical Research (2020), 53 (2), 289-299CODEN: ACHRE4; ISSN:0001-4842. (American Chemical Society) A review. Conspectus: Medicinal chem. campaigns set the foundation for streamlined mol. design strategies through the development of quant. structure-activity models. Our group’s enduring underlying interest in reaction mechanism propelled our adaptation of a similar strategy to unite mechanistic interrogation and catalyst optimization by relating reaction outputs to mol. descriptors. Through collaborative opportunities, we have recently expanded these predictive statistical modeling tools to electrocatalysis and the design of redox-active org. mols. for application as electrolytes in nonaq. redox flow batteries. Utilizing small, strategically designed data sets for a given core structure, we develop predictive statistical models that enable rapid virtual screening campaigns to identify analogs with enhanced properties. This process relates structural parameters to the output of interest, providing insight into the structural features that influence the output under study. Furthermore, the weighting of the coeffs. for each parameter in the model can furnish mechanistic insight. Such a synergistic implementation of exptl. and computational tools for mechanistic insight provides a means of forecasting properties of analogs without necessitating the synthesis and anal. of each mol. of interest. Through collaborative efforts, we have demonstrated the effectiveness of these tools for predicting diverse outputs such as stability, redox potential, and nonaq. soly. In this Account, we outline our entry into the field of org. electrochem. and the implementation of statistical modeling tools for designing org. electrolytes. Through these projects we were exposed to the power of electrochem. techniques as a mechanistic tool, which has provided access to crit. information that would otherwise be difficult to obtain. Utilizing electroanal. techniques, we have quantified the rates of disproportionation of a variety of cobalt complexes and developed statistical models that provide crit. insight into understanding of fundamental processes involved in the disproportionation of organometallic complexes. Electroanal. tools have also been effective in elucidating the active catalyst oxidn. state in different catalytic organometallic systems for C-H functionalization. Thus, our foray into electrolyte design and electrocatalysis, in which the statistical modeling tools developed for mechanistic insight were applied in a new context, came full circle to the core foundation of our group: mechanistic understanding. >> More from SciFinder [https://scifinder.cas.org/scifinder/view/link_v1/reference.jsf?l=BmxxGlm8wGqBVR2RjfkjK7Vg90H21EOLACvtfcHk0lj5zcf_3V_7LQ]https://chemport.cas.org/services/resolver?origin=ACS&resolution=options&coi=1%3ACAS%3A528%3ADC%252BB3cXlsVyltA%253D%253D&md5=8a006042cdf3084a025d57959af5bb19 (i) Siu, J. C.; Fu, N.-K.; Lin, S. Catalyzing Electrosynthesis: A Homogeneous Electrocatalytic Approach to Reaction Discovery. _Acc. Chem. Res._ 2020, _53_, 547- 560, DOI: 10.1021/acs.accounts.9b00529

• Alzaidi, O
• Wirth, T

• School of Chemistry, Cardiff University, Park Place, Main Building, Cardiff CF10 3AT, U.K

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