. 2021 Apr 30;86(10):7078–7091. doi: 10.1021/acs.joc.1c00333

Table 1. Optimization of the Reaction Conditions for the Iodocarbocyclization Reaction of 4aa^a.

entry	I⁺ source	equiv	solvent	additive	yield (%)^b
1	NIS	1.1	CH₂Cl₂	–	51
2	NIS	1.3	CH₂Cl₂	–	76 (74)^c
3^d	NIS	1.1	CH₂Cl₂	BF₃·Et₂O	56
4^e	NIS	1.3	CH₂Cl₂	BF₃·Et₂O	60
5^e	NIS	1.3	CH₂Cl₂	AcOH	50
6	I₂	1.3	CH₂Cl₂	–	–
7^e	I₂	1.3	CH₂Cl₂	Na₂CO₃	32
8^e	I₂	1.3	CH₂Cl₂	K₂CO₃	35

Reaction conditions: 4aa (0.1 mmol) and NIS (0.13 mmol) in CH₂Cl₂ (1 mL).

Determined by ¹H NMR using CH₂Br₂ as the internal standard.

Yield after column chromatography in parentheses.

With 0.11 mmol of additive.

With 0.13 mmol of additive.

Table 1. Optimization of the Reaction Conditions for the Iodocarbocyclization Reaction of 4aaa.