Table 2.

Screening of Amine additives

Entrya	Additive	3a Yield (%)	4a Yield (%)
1	–	60.5	96.8
2	NH4Cl	47.3	96.5
3	NH4OAc	62.5	95.9
4	NH4HCO3	71.6	96.3
5		43.5	95.2
6		61.5	94.1
7		68.1	93.4
8b	NH4HCO3	89.5	96.8

^aUnless otherwise specified, the reaction conditions are: Step 1: 1a (0.2 mmol),5 wt% Pd/C (5 mol%), NaBH₄ (10 mol%) in water (0.5 mL), toluene (1.5 mL), 140°C, t = 2 h. Step 2: 2a (0.4 mmol), I₂ (0.35 mmol), additive (0.4 mmol), 140°C, t = 15 h. Yield was determined by GC-FID using dodecane as an internal standard.

^b1a (0.2 mmol), 2a (0.8 mmol), NH₄HCO₃ (0.4 mmol).