Table 1.

Optimal conditions for primary pyridinium salts.

Entry[a]	Change in condition from scheme	G	1 (%)[b]
1	None	F	82 (79)
2[c]	In situ formation of acyl fluoride	F	75
3	L1 instead of L5	F	62
4	L2 instead of L5	F	65
5	L3 instead of L5	F	53
6	L4 instead of L5	F	41
7	Different G	SPy	4
8	Different G	OPy	11
9[e]	Zn instead of Mn	F	5
10[d]	No nickel	F	0
11[d]	No ligand	F	0
12[e]	No Mn reductant	F	0

^[a]Pyridinium salt (0.125 mmol, 1 equiv), acyl fluoride (0.125 mmol, 1 equiv), NiCl₂(dme) (0.0125 mmol, 10 mol %), ligand (0.0125 mmol, 10 mol %), Mn (0.1875 mmol, 1.5 equiv) was stirred in NMP (0.8 mL) at 60 °C for 24 h.

^[b]GC yield vs 1,3.5-trimethoxybenzene standard. Isolated yield in parentheses.

^[c]Carboxylic acid (0.125 mmol, 1 equiv), TFFH (0.125 mmol, 1 equiv), 1,8-bis(dimethylamino)naphthylene (0.125 mmol, 1 equiv), NMP (0.8 mL).

^[d]Significant amount of acyl fluoride recovered.

^[e]Both starting materials recovered.

G = Activating Group.