Table 3. Effects of the amounts of reagents and concentrations ^a .

Entry	1a (mmol%)	Fe(Pc) (mmol%)	PPh3 (equiv.)	Conc. (M)	Time (h)	Yield (%)	Er
1	10	10	2.0	0.1	52	80	98 : 2
2	10	10	2.0	0.5	29	88	99 : 1
3	10	10	2.0	1.0	18	91	98 : 2
4	10	10	2.0	2.0	14	97	98 : 2
5	10	10	1.5	2.0	14	91	99 : 1
6	10	10	1.1	2.0	12	68	99 : 1
7	10	10	2.0	4.0	12 (24) b	93 (88) b	99 : 1 (99 : 1) b
8	10	10	1.5	4.0	12 (48) c	92 (10) c	99 : 1 (46 : 54) c
9	10	10	1.1	4.0	12	76	99 : 1
10	10	5	1.5	4.0	21	84	99 : 1
11	10	1	1.5	4.0	18	81	99 : 1
12	10	1	2.0	4.0	36	89	99 : 1
13	5	10	1.5	4.0	38	78	99 : 1
14	5	5	1.5	4.0	24	76	99 : 1
15	3	3	1.5	4.0	39	68	99 : 1

^aReaction conditions: 3 (1.0 mmol), 4 (1.1 mmol), 1a (0.10, 0.050 or 0.030 mmol), Fe(Pc) (0.10, 0.050, 0.030 and 0.010 mmol), PPh₃ (2.0, 1.5 or 1.1 mmol), toluene (10, 2, 1, 0.5 or 0.25 mL), MS 5 Å (500 mg) at room temperature under air atmosphere unless otherwise noted. MS 5 Å was activated by heating using a heat gun (ca. 450 °C) in vacuo (ca. 0.1 mmHg) for 5 min.

^bThe reaction was performed on the 10 mmol scale.

^cPBu₃ was used instead of PPh₃.