Table 3. Optimization of reaction conditions for the Sonogashira coupling between 4-bromoanisole and phenylacetylene. Triethylamine (Et₃N) is used as the base. Borax-crosslinked Ncs are used as catalytic systems^a.

Entry	EC capsules (Pd mol%)	Surfactant (wt%)	T (°C)	Atmosphere	GC-MS conv. to product %
1	Nc-Pd(OAc)2 (0.75) + free XPhos	K-EL (2)	rt	Air	—
2	Nc-Pd(OAc)2 (0.75) + free XPhos	K-EL (5)	rt	Air	—
3	Nc-Pd(OAc)2 (0.75) + free XPhos	K-EL/Tol 9 : 1 (2)	rt	Air	—
4	Nc-Pd(OAc)2 (0.75) + free XPhos	—	rt	Air	—
5	Nc-Pd(OAc)2-XPhos (0.75)	K-EL (2)	rt	Air	4
6	Nc-Pd(OAc)2-XPhos (1.50)	K-EL (2)	rt	Air	4
7	Nc-Pd(OAc)2-XPhos (2.00)	K-EL (2)	rt	Air	17
8	Nc-Pd(OAc)2-XPhos (0.75)	K-EL (2)	45	Air	5
9	Nc-Pd(OAc)2-XPhos (0.75)	K-EL (2)	rt	N2	79, 30, 93, 52
10	Nc-Pd(OAc)2-XPhos (0.75)	K-EL (2)	16	N2	12
11	Nc-Pd(OAc)2-XPhos (0.75)	K-EL (2)	35	N2	47
12	Nc-Pd(OAc) 2 -XPhos (0.75)	K-EL (2)	45	N 2	100, 98, 100 (6 h)
13	Mc-Pd(OAc) 2 -XPhos (0.75)	K-EL (2)	45	N 2	100

^aGC-MS conversion % are determined by the ratio of the integration of product and starting material peaks.