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. Author manuscript; available in PMC: 2019 Jul 28.
Published in final edited form as: Nat Protoc. 2017 Feb 2;12(3):472–492. doi: 10.1038/nprot.2016.176

TABLE 2 |.

Troubleshooting table.

Step Problem Possible reason Solution
1A(lvii), synthesis of 1a Resulting solid is not yellow Co-crystallization of acetone The resultant crystals can contain some residual acetone, which, to the best of our knowledge, has a negligible effect on catalyst activity but will lead to a change in color (typically more orange or red). Residual acetone can be removed through azeotropic distillation in vacuo with CHCl3 (typically by dissolving the crude material in ~200 ml/g of photocatalyst)
Presence of nanoparticles Dissolve the solid in the minimum amount possible of dry acetone. Add a few drops of pentane to the acetone to cause precipitation of the desired product, and then filter through a cotton-containing pipette. Remove the solvent
Obtained solid is sticky Incomplete drying Place the obtained solid in a small Buchner fritted funnel atop a small Buchner flask. Wash the solid with Et2O and then with pentane. Repeat Step 1A(liv-lvi)
Yield is low (see ANTICIPATED RESULTS for expected yields) Incomplete crystallizationa Collect the organic solutions from Steps 1A(lii) and 1A(liii). Remove the solvent in vacuo. Dissolve the resulting solid in the minimum amount of acetone and place the resulting solution in a scintillation vial. Repeat Steps 1A(xlix-lvii)
Loss of material during washes Collect the organic solutions from Steps 1A(xlii, xliii, lii, and liii) and combine them. Remove the solvent in vacuo by rotary evaporation. Dissolve the resulting solid in the minimum amount of dichloromethane and, using an automated chromatographic machine, elute the desired product into test tubes through a prepacked silica column using a 95:5 (by volume) mixture of CH2Cl2/iPrOH. Transfer the fractions containing the product to a round-bottom flask and remove solvent from the eluate in vacuo by rotary evaporation (10 mmHg, 38 °C) to obtain pure 1a.
1B(xxiv), synthesis of 2a Resulting solid is not red Traces of ruthenium(0) particles Dissolve the solid using 400 ml of hot acetone and filter the solution through a 10 × 3 cm pad of Celite, eluting with an additional ~300 ml of hot acetone. Remove the acetone in vacuo by rotary evaporation (10 mmHg, 38 °C)
NMR analysis of 2a (see Analytical data in the ANTICIPATED RESULTS) shows the presence of other complexes Incomplete anion metathesis Dissolve the solid using ~200 ml of H2O, and add ~2 equiv. of NH4PF6 to the mixture. Sonicate the resulting suspension at room temperature for 30 min and then filter it. This procedure will afford a brick-red cake of the desired product. Proceed to dry the solid as defined in the PROCEDURE.
Obtained solid is sticky Incomplete drying Place the solid in a separatory funnel and wash with diethyl ether (~150 ml) followed by pentane (~150 ml). Collect the solid and place it under high vacuum (< 1 mmHg while heating to ~50 °C)
Yield is low (see ANTICIPATED RESULTS for expected yields) Incomplete precipitation Collect and combine the organic filtrates and remove the solvent in vacuo by rotary evaporation (10 mmHg, 38 °C). Take the crude solid up in acetone (200 ml) and, using the same precipitation method, repeat Steps 1B(xvi-xxiv) using a quarter of the solvent volumes listed.
a

The procedures described in the second paragraph of the Solution column can be applied to address both possible reasons reported for low 1a yield.