Table 2.

Asymmetric synthesis of biaryls by enantioselective Suzuki-Miyaura coupling.^a

Entry	R	R′	X	Yield %b	ee %c
a	Me	H	Cl	87	93(R)
b	Me	H	Br	83	93(R)
c	Me	H	I	81	94(R)
d	OEt	H	Cl	81	91(S)
e	OEt	H	Br	80	91(S)
f	Me	4-F	Br	83	93(R)
g	OEt	4-F	Br	81	90(S)
h	Me	4-Me	Br	82	94(R)
i	OEt	4-Me	Br	81	92(S)
j	Me	4-NO2	Br	92	88(R)
k	Me	5-OMe	Br	83	94(R)
l	OEt	5-OMe	Br	84	91(S)
m	Me	5-CF3	Br	87	89(R)
n	Me	5-F	Br	85	92(R)
o	Me	6-Me	Br	80	48(R)
p	Me	6-F	Br	46	90(R)

^aReaction conditions: 1.0 equiv of aryl halide, 1.5–2.0 equiv of boronic acid, (S)-1/Pd(OAc)₂ = 1.2, 3 equiv of K₃PO₄, THF (2.5–3 mL/mmol of halide).

^bIsolated yield (average of two runs).

^cThe ee values were determined by chiral HPLC on a Chiralcel OD-H or AD-H.

The absolute configuration of 14h was determined by X-ray crystallography. The configurations of other biaryl compounds were assigned by analogy.