Iodine-Mediated Neutral and Selective N-Boc Deprotection

Table 1

Effect of solvents on iodine-mediated de-N-tert-butoxycarbonylation of N-Boc-aniline (1a)^a.

Entry	Solvent	Time	Yield^b (%)
1	DCM	5 h	94
2	CH3CN	6 h	92
3	Benzene	9 h	88
4	Toluene	12 h	82
5	No solvent	30 min	98

^aAll the reactions were carried out using the tert-butyl phenylcarbamate (1a, 1.0 mmol) and iodine (0.08 mmol) at room temperature.
^bIsolated yield.