Table 1.

Optimization of Reaction Conditions for Pd-Catalyzed C(sp³)–H Carbonylation^a

entry	additive	solvent	yield (%)b
1	none	DMF	<1
2	none	toluene	7
3	none	C6F6	8
4	none	n-hexane	30
5	BQ	n-hexane	13
6	Cu(OAc)2	n-hexane	4
7	DMF	n-hexane	54
8	PivOH	n-hexane	50
9	TEMPOc	n-hexane	80
10	TEMPO	n-hexane	95

^aReaction conditions: 1a (0.1 mmol), Pd(OAc)₂ (10 mol %), AgOAc (2.0 equiv), KH₂PO₄ (2.0 equiv), additive (2.0 equiv), solvent (1 mL), CO (1 atm), 130 °C, 18 h.

^bThe yield was determined by ¹H NMR analysis of the crude product using 1,1,2,2-tetrachloroethane as an internal standard.

^cTEMPO (0.2 equiv).