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. Author manuscript; available in PMC: 2012 May 23.
Published in final edited form as: Angew Chem Int Ed Engl. 2011 Apr 21;50(22):5125–5129. doi: 10.1002/anie.201101147

Table 2.

Regioselective cross-couplings of tribrominated biaryls.

graphic file with name nihms365148u2.jpg
entry product R= substrate % yielda (% rec. SM) regioselectivityb,c,d (A:B:C) SM er Pdt ere,f
1 graphic file with name nihms365148t7.jpg
14a 		9 70 (20) 11.0:1.0:1.0 95.0:5.0
97.0:3.0
2 graphic file with name nihms365148t8.jpg
14b 		9 48 (20) 17.0:1.0:1.0 95.0:5.0
98.0:2.0
3 graphic file with name nihms365148t9.jpg
14c 		9 55 (20) >30.0:1.0:1.0 95.0:5.0
97.5:2.5
4 graphic file with name nihms365148t10.jpg
14d 		9 52 (23) 24.0:2.0:1.0 95.0:5.0
94.5:4.5
5 graphic file with name nihms365148t11.jpg
14e 		9 49 5.0:1.0:1.0 95.0:5.0
95.0:5.0
6 graphic file with name nihms365148t12.jpg
15a 		10 45 (19) 10.0:1.0:1.0 95.0:5.0
97.0:3.0
7 graphic file with name nihms365148t13.jpg
15b 		10 45 (30) 10.0:1.0:-- 95.0:5.0
95.5:4.5
8 graphic file with name nihms365148t14.jpg
15c 		10 52 (23) 14.0:1.0:1.0 95.0:5.0
96.0:4.0
a

Average isolated yields of three experimental runs.

b

Assigned by NMR analysis.

c

Ratio determined by 1H NMR.

d

Averaged over three experimental runs.

e

Enantiomer ratios were determined by HPLC analysis.

f

Averaged over three runs.