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. Author manuscript; available in PMC: 2022 Aug 1.
Published in final edited form as: Org Biomol Chem. 2022 Jun 1;20(21):4314–4319. doi: 10.1039/d2ob00439a

Table 2.

TEMPO oxidation of p-nitrobenzalcohol 12a

graphic file with name nihms-1825201-t0008.jpg
entry catalyst Time (h)[b] 21 Yield (%)[c]
1 14 4 >98
2 (RR,RR)-12 5.5 >98
3 (R,R)-1 24 ND
4 (RR,RR)-1 + Zn(OAc)2 24 ND
5[d] (RR,RR)-12 Repeat #8 8 87
6[d][e] (RR,RR)-12 Renewed, Repeat #3 5.5 >98
[a]

p-Nitrobenzaldehyde 7 (1.0 mmol), DIB (1.02 mmol) and catalyst (20 mol%) in DMF.

[b]

Monitored by GC.

[c]

An isolated yield after column purification (Hex:EtOAc = 7:3 to 5:5).

[d]

Renewed catalyst was used.

[e]

3rd reaction cycle using the renewed catalyst. ND: not determined.

ND: not determined.