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. Author manuscript; available in PMC: 2018 Aug 23.
Published in final edited form as: J Am Chem Soc. 2017 Aug 14;139(33):11595–11600. doi: 10.1021/jacs.7b06794

Table 6.

Comparing the dehydrohalogenation of alkyl bromide and iodide ATRC intermediates.

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entry conditions conversion (%)a yield (%)a
1 X = Br, no additive 100 100
2 X = I, no additive 100 97
3 X = Br, with 10 mol % dinitrobenzene 22 9
4 X = I, with 10 mol % dinitrobenzene 100 100
5 X = Br, no metal or ligand <2 <2
6 X = I, no metal or ligand 56 37
a

Determined by 1H NMR spectroscopy using 1,3,5-trimethoxybenzene as internal standard. For details regarding the distribution of minor regioisomers, see Supporting Information.