Table 3.

Optimization of Photoinduced Method To Produce 2-Phenyl-1,2-benzisoselenazol-3(2H)-ones^a

entry	equiv, catalyst	halogen	energy	yield (%)
1	1.0, phen-CuI	4b	thermal reaction	1a: 89b
2	1.0, phen-CuI	4b	22 W Hg lamp	1a: 31
3	1.0, CuI	4b	22 W Hg lamp	1a: 82
4	0.1, CuI	4b	22 W Hg lamp	1a: 60c
5		4b	22 W Hg lamp	1a: N.R.
6	1.0, CuI	4b	dark	1a:6
7	1.0, CuI	4b	22 W Hg lamp	1a: N.R.
8	1.0, CuI	4b	ambient light	1a: 21
9	1.0, CuI	4b	250 W infrared lamp	1a: 63d
10	0.1, CuI	4b	22 W Hg lamp	1a: 81c,e
11	1.0, CuI	4c	22 W Hg lamp	1a: 92
12	1.0, CuI	4a	22 W Hg lamp	1a: N.R.
13	1.0, CuI	5o	22 W Hg lamp	1o: 85
14	1.0, CuI	4b	14 W Hg lamp	1a: 77f

^aUnless otherwise stated, KSeCN (2.5 equiv) and Cs₂CO₃ (1.2 equiv) 24 h, and acetonitrile were used. Reactions were cooled for about 2 h and allowed to warm to room temperature (20 °C).

^bThermal activation = phen-CuI (1.0 equiv), KSeCN (1.2 equiv), Cs₂CO₃ (2.5 equiv), 12 h, 100–110 °C.

^c48 h.

^dReaction reached 65–70 °C.

^eNaOtBu (0.1 equiv). N.R = no reaction. 22 W is a combined wattage of two lamps.

^fReaction performed without BLE-8T365 (320–400 nm) lamp; only the 14 W Rayonet RPR-3000A lamp was used.