Table 1.

Optimization of the key Suzuki-Miyaura coupling of vinyl bromide 5 and boronic monoester 4.^a

entry	Ligand (0.2 equiv)	Base (3 equiv)	Suzuki-Miyaura couplingb	C-H insertionb
1	SPhosc	Cs2CO3	trace	30%
2	SPhosd	Cs2CO3	trace	51%
3	PPh3	Cs2CO3	trace	2%
4	Xantphos	Cs2CO3	trace	21%
5	dppp	Cs2CO3	trace	trace
6	dppf	Cs2CO3	trace	17%
7	RuPhos	CsF	47%	trace
8	SPhos	K2CO3	34%	22%
9	SPhos	K3PO4	10%	17%
10	APhos	Cs2CO3	40%	12%
11	APhose,f	Cs2CO3	74%	trace

^aStandard conditions: 10% Pd(OAc)₂, ligand (0.2 equiv), base (3 equiv), PhMe (0.1M), 65 °C.

^bYields refer to purified, isolated products.

^cReaction temperature was 110 °C.

^dConcentration: 0.01M.

^eSlow addition of the catalyst (0.1 mL/h, over 3 h) as a toluene solution.

^fConcentration: 0.2 M.