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. Author manuscript; available in PMC: 2019 Oct 10.
Published in final edited form as: J Am Chem Soc. 2018 Oct 2;140(40):12829–12835. doi: 10.1021/jacs.8b05870

Figure 3.

Figure 3

Mechanistic studies. (a) Proposed mechanism for the reactivity between EBXs and phenols under the influence of visible light. Thermochemistry evaluation was conducted at the M06/Lanl2dz level of theory with CPCM-described solvation in acetonitrile; CPCM: conductor-like polarizable continuum model. Time-dependent density functional theory (TD-DFT) calculations to model the lowest excited states of the EDA complex were conducted at the CAM-B3LYP/Lanl2dz/CPCM-MeCN level of theory. HOMO: highest occupied molecular orbital; LUMO: lowest unoccupied molecular orbital; f: predicted oscillator strength. λcalc: predicted maximum wavelength of absorption of the lowest excited state. (b) 13C-labeling experiment. (c) Experiment involving deuterated phenol. (d) Experiment involving vinylbenziodoxolone and sodium phenoxide. (e) Light-driven reaction between EBX 2a, diboronate ester, and pyridine to yield (iodoethynyl)benzene.