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. Author manuscript; available in PMC: 2020 Nov 13.
Published in final edited form as: J Am Chem Soc. 2019 Nov 1;141(45):18160–18169. doi: 10.1021/jacs.9b08894

Table 1.

Ligand Effect on Co(II)-Based Metalloradical System for Asymmetric 1,5-C–H Amination of Arylsulfonyl Azidea

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entry catalyst temp (°C) solvent yield (%) ee (%)
1 [Co(P1)] 80 chlorobenzene 99 28
2 [Co(P2)] 80 chlorobenzene 99 32
3 [Co(P3)] 80 chlorobenzene 99 49
4 [Co(P4)] 80 chlorobenzene 99 84
5 [Co(P4)] 60 chlorobenzene 99 86
6 [Co(P4)] 40 chlorobenzene 63 88
7 [Co(P4)] 60 chloroform 70 89
8b [Co(P4)] 50 chloroform 96 92
graphic file with name nihms-1057584-t0003.jpg
a

Reactions were carried out for 18 h on 0.10 mmol scale under N2; [1a] = 0.25 M. Isolated yields Enantiomeric excess determined by chiral HPLC.

b

4 mol % catalyst for 48 h.