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. Author manuscript; available in PMC: 2011 Aug 18.
Published in final edited form as: J Am Chem Soc. 2010 Aug 18;132(32):11278–11287. doi: 10.1021/ja104297g

Table 1.

Effect of functional group located ortho to the halide substituent on the enantioselectivity.

graphic file with name nihms224529u2.jpg
R = NEt2, X = Br (6) R = N(Me)tBu, X = Br (10)
R = NEt2, X = I (7) R = N(OMe)Me, X = Br (11)
R = NEt2, X = OTf (8) R = N(H)tBu, X = Br (12)
R = NiPr2, X = Br (9) R = N(H)C(Me)2Ph, X = Br (13)
Entry ArX Temp (°C) Yield %b ee %c
a 6 rt 80 75
b 7 rt 78 73
c 8 rt 85 71
d 9 rt 76 82
e 10 rt 82 75
f 11 rt 75 80
g 12 50 68 87
h 13 50 81 93
a

Reaction conditions: 1.0 equiv of aryl halide, 2.0 equiv of boronic acid, 5 mol% Pd, 6 mol% (S)-1, 3 equiv of K3PO4, THF (2.5–3 mL/mmol of halide), 24–40 h.

b

Isolated yield.

c

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