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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 4.

Regioselective cross-couplings of dibrominated p-terphenyls.

graphic file with name nihms365148u4.jpg
entry substrate product % yield (% rec. SM)b regioselectivityc,d,e SM er Pdt era
1 14b graphic file with name nihms365148t18.jpg
16 		52 (20) 10.0:1.0 98.0:2.0
99.0:1.0
2 14b graphic file with name nihms365148t19.jpg
17 		65 (10) 5.0:1.0 98.0:2.0
99.0:1.0
3 15c graphic file with name nihms365148t20.jpg
18 		41 (24) 7.0:1.0 96.0:4.0
95.0:5.0
4 15c graphic file with name nihms365148t21.jpg
19 		52 (18) 6.0:1.0 96.0:4.0
95.0:5.0
5 14h graphic file with name nihms365148t22.jpg
20 		37 (36) 2.5:1.0f 96.0:4.0
95.0:5.0
a

Enantiomer ratios were determined by chiral HPLC.

b

Average isolated yield of three experimental runs.

c

Assigned by NMR analysis.

d

Ratio determined by 1H NMR.

e

Averaged over three experimental runs.

f

Isolated as single regioisomer in 25 % overall yield