Optimization of CuO/CNF for the synthesis of alkenyl boronates using phenylacetylene and bis(pinacolato)diboron^a.

Entry	Catalyst (mg)	Base	Temp. (°C)	Conv.b (%) 3aa
1	CuO/CNF (2)	—	25	59
2	CuO/CNF (2)	—	40	74
3	CuO/CNF (2)	K2CO3	40	82
4	CuO/CNF (2)	KOtBu	25	87
5	CuO/CNF (2)	KOtBu	40	98 (93)c
6	CuO/CNF (2)	KOtBu	40	69d
7	Recovered from #5	KOtBu	40	96
8	Recovered from #7	KOtBu	40	94
9	Recovered from #8	KOtBu	40	91
10	Recovered from #9	KOtBu	40	89

^aExperimental conditions: phenylacetylene (0.49 mmol), B₂Pin₂ (0.588 mmol), CuO/CNF (2 mg), base (10 mol%), methanol (1 mL) under argon, 40 °C, 12 h.

^bConversion determined by GC-MS.

^cIsolated yield.

^d0.98 mmol of phenylacetylene were used.