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. 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 9.

Reactions of Vinylnaphthalene

graphic file with name nihms210777t89.jpg
Entry Oxidant/Solvent X Yielda Ratio 1,2 : 1,1a
1 PhICl2/CH2Cl2 Cl 60%b > 50 :1
2 CuCl2/Et2O Cl 76% > 50 : 1
3c CuBr2/THF Br 12%d > 50 : 1
4c CuBr2/Et2O Br 48%d > 50 : 1
a

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

b

Mass balance in 1,2-chlorination is accounted for by formation of 25% of the 1,2-dichloro product.

c

Pd(acac)2 used as [Pd].

d

Mass balance in arylbromination reactions is predominantly accounted for by incomplete conversion (15% conversion of vinylnaphthalene in entry 3 and 70% conversion of vinylnaphthylene in entry 4).