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. Author manuscript; available in PMC: 2020 Apr 3.
Published in final edited form as: J Am Chem Soc. 2019 Sep 9;141(37):14570–14575. doi: 10.1021/jacs.9b08662

Table 3.

Deuteration of Cyclic Amino C─H Bonds a,b

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a

Conditions: N-alkylamine (1, 0.2 mmol), acetone-d6 (2, 1.36 mmol), B(C6F5)3 (10 mol%), toluene (0.8 mL), under N2, 150 °C, 3 h.

b

Yield of isolated and purified product. Deuterium incorporation level was determined by 1H NMR analysis of the isolated and purified product.

c

Green label indicates sites that are beta to N. Red label is used for any other sites that undergo deuteration.

d

Conditions: N-alkylamine (1, 0.2 mmol), acetone-d6 (2, 1.4 mmol), B(C6F5)3 (5.0 mol%), toluene (0.8 mL), under N2, 150 °C, 3 h. After the filtration of the crude reaction mixture through a pad of silica gel and removal of volatiles, acetone-d6 (2, 1.4 mmol), B(C6F5)3 (5.0 mol%), and toluene (1.0 mL) were added under N2, and then heated at 150 °C, 3 h.

e

The reaction was carried out in two batches, using 10 mol% of B(C6F5)3 in the first batch, and 5.0 mol% in the second. For details, see the SI.