Table 2. Stability tests for TIMs toward different reagents and in buffers at different pHs.

Entry	Conditions	Conversion a
		2 h	16 h	24 h
1	Et3N (5.00 equiv.)			0%
2	Piperidine (20.0 equiv.)			0%
3	CF3CO2H (0.1 mL) b			0%
4	aq. HCl (0.1 M, pH 1.2)			0%
5	aq. citric acid (0.1 M, pH 2.0)			0%
6	aq. citric acid/K2HPO4 buffer (0.1 M, pH 3.0)	0%	2%
7	aq. citric acid/K2HPO4 buffer (0.1 M, pH 5.0)	2%	5%
8	aq. KH2PO4/K2HPO4 buffer (0.1 M, pH 7.0)	4%	14%	19%

^aConversion determined using LC-MS.

^bCH₂Cl₂ used as solvent instead of CH₃CN. Solvolysis of the BF₃ group was never observed under aqueous conditions.