Fig. 4 XANES spectra [red line, 0.6 mmol of CuI and 12 mmol of LiCl in 12 ml of DMA at room temperature (rt) under N2 for 5 min; black line, 0.6 mmol of CuI and 12 mmol of LiCl in 12 ml of DMA at rt under air for 5 min; brown line, 0.6 mmol of CuI, 12 mmol of LiCl, and 30 mmol of 2a in 12 ml of DMA at rt under air for 5 min; green line, 0.6 mmol of CuI, 12 mmol of LiCl, and 30 mmol of 2a in 12 ml of DMA at 120°C under air for 5 min]. Fig. 6 Density functional theory (DFT) calculations for intramolecular cyclization of the enamine cationic radical. (A) Free energy profile for copper(II)-involved cyclization. (B) ESP map of complex IX. (C) Spin density map of complex IX. The numbers in parentheses are the corresponding Mulliken spin density located on each atom.
Supplementary Materials
Supplementary material for this article is available at http://advances.sciencemag.org/cgi/content/full/1/9/e1500656/DC1
General information
General procedure
Table S1. The evaluation of several metal salts.
Table S2. The effects of other solvents.
Table S3. The effects of reaction temperature.
Table S4. The effects of the ratio of substrates.
Table S5. The effects of LiCl loading.
Table S6. Oxidative C–H/N–H coupling between ketone and ethylenediamine under standard reaction conditions.
Scheme S1. Gas chromatography–mass spectrometry analysis of the reaction between 1a and 2a.
Scheme S2. Gas chromatography–mass spectrometry analysis of the reaction between 1a and 2e.
EPR experiments
Radical trapping experiments
Scheme S3. Radical trapping experiment using BHT [2,6-bis(1,1-dimethylethyl)-4-methylphenol] as the scavenger.
Scheme S4. Radical trapping experiment using TEMPO (2,2,6,6-tetramethylpiperidinyloxy) as the scavenger.
XAS experiments
General computational calculation details
Detailed descriptions for products
NMR data
References (65–73)
Additional Files
Supplementary Materials
This PDF file includes:
- General information
- General procedure
- Table S1. The evaluation of several metal salts.
- Table S2. The effects of other solvents.
- Table S3. The effects of reaction temperature.
- Table S4. The effects of the ratio of substrates.
- Table S5. The effects of LiCl loading.
- Table S6. Oxidative C–H/N–H coupling between ketone and ethylenediamine under standard reaction conditions.
- Scheme S1. Gas chromatography–mass spectrometry analysis of the reaction between 1a and 2a.
- Scheme S2. Gas chromatography–mass spectrometry analysis of the reaction between 1a and 2e.
- EPR experiments
- Radical trapping experiments
- Scheme S3. Radical trapping experiment using BHT 2,6-bis(1,1-dimethylethyl)-4-methylphenol as the scavenger.
- Scheme S4. Radical trapping experiment using TEMPO (2,2,6,6-tetramethylpiperidinyloxy) as the scavenger.
- XAS experiments
- General computational calculation details
- Detailed descriptions for products
- NMR data
- References (65–73)
Files in this Data Supplement:
