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. Author manuscript; available in PMC: 2013 Oct 5.
Published in final edited form as: J Org Chem. 2012 Sep 26;77(19):8648–8656. doi: 10.1021/jo3016192

Table 2.

Pd-Catalyzed Annulation of Benzyne 2aa

graphic file with name nihms410817t2.jpg
entry substrate % yield
of 3b 		entry substrate % yield
of 3b
1 graphic file with name nihms410817t3.jpg (3a) 73 14 graphic file with name nihms410817t4.jpg (3n) 74
2 graphic file with name nihms410817t5.jpg (3b) 70 15 graphic file with name nihms410817t6.jpg (3o) 74
3 graphic file with name nihms410817t7.jpg (3c) 87 16 graphic file with name nihms410817t8.jpg (3p) 70
4 graphic file with name nihms410817t9.jpg (3d) 64 17 graphic file with name nihms410817t10.jpg (3q) 67
5 graphic file with name nihms410817t11.jpg (3e) 65 18 graphic file with name nihms410817t12.jpg (3r) 52
6 graphic file with name nihms410817t13.jpg (3f)--c 19 graphic file with name nihms410817t14.jpg (3s) 65
7 graphic file with name nihms410817t15.jpg (3g) 82 20 graphic file with name nihms410817t16.jpg (3t) 79
8 graphic file with name nihms410817t17.jpg (3h) 77 21 graphic file with name nihms410817t18.jpg (3u) 70
9 graphic file with name nihms410817t19.jpg (3i) 75 22 graphic file with name nihms410817t20.jpg (3v) 55
10 graphic file with name nihms410817t21.jpg (3j) 83 23 graphic file with name nihms410817t22.jpg (3w) 36
11 graphic file with name nihms410817t23.jpg (3g) 38 24 graphic file with name nihms410817t24.jpg (3x) 0
12 graphic file with name nihms410817t25.jpg (3l) 84 25 graphic file with name nihms410817t26.jpg (3y) 0
13 graphic file with name nihms410817t27.jpg (3m) 79
a

Representative procedure: 1 (0.25 mmol), 2.0 equiv of 2, 5.0 equiv of CsF, 5 mol % Pd(OAc)2, 10 mol % dppm, 1.0 equiv of Na2CO3 in 5 ml of 4:1 toluene/MeCN at 110 °C for 16–24 h.

b

Isolated yield.

c

An unknown mixture was generated with products overlapping with the starting material 1d on the TLC plate.