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. Author manuscript; available in PMC: 2021 May 11.
Published in final edited form as: Angew Chem Int Ed Engl. 2020 Mar 17;59(20):7921–7927. doi: 10.1002/anie.201916710

Table 1.

Reaction conditions for the direct decarboxylative alkylation (DDA) of anilines.[a]

graphic file with name nihms-1576805-t0009.jpg
Entry Change from optimal conditions Yield, %[b]
1 No change 99 (97[c])
2 No light 0
3 No A1 0
4 No Cu(hfac)2 0
5 No DTBP 7
6 A2 instead of A1 86
7 Cu(acac)2 instead of Cu(hfac)2 38
8 PhCF3 instead of EtOAc 78
9 PhCH3 instead of EtOAc 76
10 420 nm instead of 400 nm LED 86
11 Under air 94
[a]

Reaction conditions: aniline (0.3 mmol), carboxylic acid (0.75 mmol), A1 (10 mol%), Cu(hfac)2 (10 mol%), DTBP (0.6 mmol), EtOAc (4.5 mL), LED (400 nm), 12 h.

[b]

Determined by 1H NMR with 1,4-dimethoxybenzene as an internal standard.

[c]

Isolated yield.