Table 2. Coupling Reaction between Phenylboronic Acid and Different >P(O)H Reagents.

						product composition (%)a,b
entry	Y1, Y2	base	solvent	t (h)	conversion (%)a	1	Ar3PO	yield (%)
1	Ph	Cs2CO3	EtOH	1.5	100b	95c		83 (1a)
2	Ph	K2CO3	MeCN	2.5	96	96		78 (1a)
3	4-MeC6H4	Cs2CO3	EtOH	2	100	85	15	78 (1b)
4	4-MeC6H4	K2CO3	MeCN	3	100	81	19	72 (1b)
5	3,5-diMeC6H3	Cs2CO3	EtOH	2.5	100	88	12	74 (1c)
6	3,5-diMeC6H3	K2CO3	MeCN	4	100	79	21	56 (1c)
7	EtO	Cs2CO3	EtOH	4	100	100		84 (1d)
8	EtO	Cs2CO3	EtOH	0.5d	100	100		82 (1d)
9	EtO	K2CO3	MeCN	4	63	63
10	EtO	K2CO3	MeCN	2d	100	100		73 (1d)
11	EtO, Ph	Cs2CO3	EtOH	4	100	100		82 (1e)
12	EtO, Ph	Cs2CO3	EtOH	0.5d	100	91e		86 (1e)

^aOn the basis of relative ³¹P NMR intensities.

^bThe average of two or three parallel experiments.

^c5% of (EtO)Ph₂PO as the byproduct.

^dThe temperature was 150 °C.

^e9% of (EtO)₂PhPO as the byproduct.