Table 1.

Heck cyclization of 10 Using Different Palladium Catalysts

	Reaction Conditions						Oxindole
entry	substrate	catalysta	Additiveb	Solvent	T (°C)	t (h)	Yield, %c	11:12d
1	10a	Pd(Ph3P)4	Et3N	MeCN	82	18	81	66:34
2	10b	Pd(Ph3P)4	Et3N	MeCN	82	15	66	60:40
3	10b	Pd(Ph3P)4	Et3N	THF	66	24	20f	60:40
4	10b	Pd(dppe)e	Et3N	THF	66	24	46f	55:45
5	10b	Pd(dppf)e	Et3N	THF	66	36	(18)	50:50
6	10b	Pd2(dba)3	Et3N	THF	66	24	75f	73:27
7	10b	Pd2(dba)3	Et3N	PhMe	110	1	80–95g	89:11
8	10b	Pd2(dba)3	Ag3PO4	THF	66	36	77	3:97

^a10–20% was employed.

^b10–15 equiv of Et₃N or 2 equiv of Ag₃PO₄ (per equiv of 10) was employed.

^cIsolated yields of the isomer mixture, yields in parentheses are % conversion by capillary GC analysis (peak area % without calibration).

^dCapillary GC or 500 MHz ¹H NMR analysis; in contrast to the methyl analog, isomers 11b and 12b could not be separated on silica gel.

^ePrepared in situ from 1 equiv of Pd₂(dba)₃ and 2 equiv of the diphosphine.

^fThe majority of the remaining mass was recovered 10b

^gMultiple experiments conducted with 100–300 mg of 10b.