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. Author manuscript; available in PMC: 2022 Apr 28.
Published in final edited form as: J Am Chem Soc. 2021 Apr 15;143(16):6065–6070. doi: 10.1021/jacs.1c02747

Table 1.

Optimization of Oxidative Amination

graphic file with name nihms-1748416-t0003.jpg
entry[a] photocat. oxidant % yield[b]
1 MesAcrPh+ CuBr2 0%
2 MesAcrPh+ Cu(OTf)2 3%
3 MesAcrPh+ Cu(OAC)2 48%
4 MesAcrPh+ CU(TFA)2 57%
5 MesAcrPh+ Cu(OPiv)2 57%
6 MesAcrPh+ CU(EH)2 87%
7 MesAcrMe+ CU(EH)2 52%
8 TPPT Cu(EH)2 24%
9[c] MesAcrPh+ Cu(EH)2 28%
10 none CU(EH)2 0%
11 MesAcrPh+ none 0%
12[d] MesAcrPh+ CU(EH)2 0%
graphic file with name nihms-1748416-t0004.jpg
[a]

Reactions conducted using 1 (0.1 mmol), oxidant (2 equiv), TFA (1 equiv), and photocatalyst (2.5 mol%) in degassed 1,2-DCE and irradiated with a 15 W blue LED flood lamp for 16 h.

[b]

Yields were determined by 1H NMR analysis of the unpurified reaction mixtures using phenanthrene as an internal standard.

[c]

Reaction conducted in absence of 1 equiv TFA.

[d]

Reaction vessel was covered in aluminum foil.