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. Author manuscript; available in PMC: 2011 Apr 16.
Published in final edited form as: J Org Chem. 2010 Apr 16;75(8):2756–2759. doi: 10.1021/jo100344k

TABLE 3.

Synthesis of Other Heterocycles Using Aryl Chlorides as Electrophilesa

entry substrate product yieldb
1 graphic file with name nihms189339t31.jpg
8
graphic file with name nihms189339t32.jpg
14
77%
2 graphic file with name nihms189339t33.jpg
9
graphic file with name nihms189339t34.jpg
15
81% (20:1 dr)
3 graphic file with name nihms189339t35.jpg
10
graphic file with name nihms189339t36.jpg
16
73%
4 graphic file with name nihms189339t37.jpg
11
graphic file with name nihms189339t38.jpg
17
89%c
5 graphic file with name nihms189339t39.jpg
12
graphic file with name nihms189339t40.jpg
Not observed
18
0%
6 graphic file with name nihms189339t41.jpg
13
graphic file with name nihms189339t42.jpg
19
Not observed
0%
a

Conditions: substrate (1 equiv), aryl chloride (1.2 equiv), NaOtBu (1.2 equiv), Pd(OAc)2 (2 mol %), S-Phos (4 mol %), toluene (0.25 M), 90 °C or 110 °C.

b

Isolated yield (average of two or more experiments).

c

This material was obtained as a 13:1 mixture of regioisomers.