Table 1. Investigation of NIS Reagent Loading Under Anaerobic and Aerobic Conditions: Catalyzed Umpolung Amide Synthesis.

entrya	O2b	NIS amount (mol %)	yield (%)c
1	no	100	69
2	no	75	52
3	no	50	36
4	no	30	25
5	no	20	20
6	no	10	20
7	no	0	19
8	yes	20	76
9	yes	10	73
10	yes	5	76
11	yes	1	55
12e	yes	0	51
13e	yesd	5	69

^aReactions are 0.2 M in nitroalkane and employ 1.2 equiv of amine and 5 equiv of H₂O and run for 24 h. Under anaerobic conditions (entries 1–7), NIS was added once the nitroalkane was no longer visible by TLC, indicating that the nitronate predominated (see Supporting Information).

^bAll solutions were first degassed (freeze–pump–thaw cycles), and entries not using oxygen were performed under an argon atmosphere (balloon), whereas entries using oxygen were performed under an oxygen atmosphere (balloon).

^cIsolated yield.

^dOpen to air.

^e48 h reaction time.