. 2023 Nov 19;8(48):45867–45877. doi: 10.1021/acsomega.3c06594

Table 1. Optimization of the Reaction Conditions^a.

entry	solvent	base	T (°C)	yield (%)^b
1	DMF	Cs₂CO₃	110	81
2	DMSO	Cs₂CO₃	110	68
3	toluene	Cs₂CO₃	110	12
4	1,4-dioxane	Cs₂CO₃	110	36
5	MeCN	Cs₂CO₃	110	81
6	MeCN	Cs₂CO₃	100	87
7	MeCN	Cs₂CO₃	90	93
8	MeCN	Cs₂CO₃	80	90
9	MeCN	Na₂CO₃	90	63
10	MeCN	t-BuOK	90	43
11	MeCN		90	15
12	MeCN	Cs₂CO₃	90	78^c
13	MeCN	Cs₂CO₃	90	90^d

Reaction conditions: 1a (0.3 mmol, 1.0 equiv), 1b (0.3 mmol, 1.0 equiv), and base (0.6 mmol, 2.0 equiv) in solvent (2.0 mL) for 24 h.

The yields were determined by ¹H NMR analysis using 1,3,5-trimethoxybenzene as the internal standard.

Gram-scale (10 mmol scale) reaction.

(3-Bromoprop-1-yn-1-yl)benzene 1e was used.

Table 1. Optimization of the Reaction Conditionsa.