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. Author manuscript; available in PMC: 2011 Nov 5.
Published in final edited form as: Org Lett. 2010 Nov 5;12(21):4876–4879. doi: 10.1021/ol102039c

Table 2.

Cross-Coupling of 4a with Diverse Aryl Chlorides

graphic file with name nihms241428u3.jpg
entry chloride product % isolated yield
1 graphic file with name nihms241428t17.jpg graphic file with name nihms241428t18.jpg 5a 87
2 graphic file with name nihms241428t19.jpg graphic file with name nihms241428t20.jpg 5b: R1 = H 83 (91)a
5c: R1 = Me 88b
3 graphic file with name nihms241428t21.jpg graphic file with name nihms241428t22.jpg 5d 65a
4 graphic file with name nihms241428t23.jpg graphic file with name nihms241428t24.jpg 5e: R1 = CN 87
5f: R1 = CHO 88
5g: R1 = Ac 88
5 graphic file with name nihms241428t25.jpg graphic file with name nihms241428t26.jpg 5h 98
6 graphic file with name nihms241428t27.jpg graphic file with name nihms241428t28.jpg 5i 95 (91)c
7 graphic file with name nihms241428t29.jpg graphic file with name nihms241428t30.jpg 5j 74
8 graphic file with name nihms241428t31.jpg graphic file with name nihms241428t32.jpg 5k 87
9 graphic file with name nihms241428t33.jpg graphic file with name nihms241428t34.jpg 5l 89
10 graphic file with name nihms241428t35.jpg graphic file with name nihms241428t36.jpg 5m 76

All reactions were carried out using 0.3 mmol of 4a and aryl chloride, 2.5 mol % Pd(OAc)2, 5 mol % XPhos, 0.9 mmol of Cs2CO3, 10:1 CPME/H2O (0.09 M), 85 °C, 6 h.

a

Used 5 mol % Pd(OAc)2, 10 mol % XPhos.

b

Heated reaction for 14 h.

c

Reaction performed on 4.1 mmol scale using 1 mol % Pd(OAc)2 and 2 mol % XPhos, 24 h at 85 °C.