Skip to main content
. Author manuscript; available in PMC: 2011 Jun 23.
Published in final edited form as: J Am Chem Soc. 2010 Jun 23;132(24):8419–8427. doi: 10.1021/ja101851v

Table 12.

Arylhalogenation of cis-48 and trans-48a

graphic file with name nihms210777t92.jpg
Entry Substrate Oxidant Solvent Yieldb,c Ratio 49 : 50b
1 cis-48 PhICl2 CH2Cl2 40% 12 : 1
2 cis-48 CuCl2 Et2O 51% >30 : 1
3 cis-48 CuBr2 Et2O 41% 5 : 1
4 trans-48 PhICl2 CH2Cl2 21% 1 : 1.6
5 trans-48 CuCl2 Et2O 45% 1 : 8
6 trans-48 CuBr2 Et2O 9% 1 : 8
a

Conditions: 2 equiv PhSnBu3, 10 mol % PdCl2(PhCN)2, 0.032 M, −78 → 23 °C, 36 h.

b

Yield and selectivity determined by 1H NMR spectroscopic analysis of crude reaction mixture.

c

The mass balance in these reactions is accounted for by recovered starting material as well as the corresponding Mizoroki-Heck product. See Supporting Information for full details.