Table 1. Optimization of the reaction conditions ^a .

Entry	LAG	Milling frequency (Hz)	Time (min)	NMR yield b (%)
1	None	30	30	40
2	None	30	60	43
3	THF	30	30	71
4	Toluene	30	30	61
5	CH3CN	30	30	71
6	Dioxane	30	30	64
7	DMF	30	30	64
8	Et2O	30	30	66
9	DMSO	30	30	55
10	Pentane	30	30	58
11	Cyclohexane	30	30	47
12	MeOH	30	30	48
13	THF	25	30	78 e
14 c	THF	25	30	55
15 d	THF	25	30	67
16	THF	25	10	71

^aConditions: 1 (0.05 mmol), 2a (0.05 mmol), RuPhos (0.05 mmol), and the LAG additive (0.2 μL mg^–1) in a stainless-steel ball-milling jar (1.5 mL) with a stainless-steel ball (3 mm).

^bDetermined by ¹H NMR analysis of the crude reaction mixture using an internal standard.

^cTwo stainless-steel balls (3 mm) were used.

^dThree stainless-steel balls (3 mm) were used.

^eIsolated yield.