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. 2011 Sep 16;13(18):4974-6.
doi: 10.1021/ol202098h. Epub 2011 Aug 24.

An improved palladium-catalyzed conversion of aryl and vinyl triflates to bromides and chlorides

Jun Pan  1 , Xinyan Wang, Yong Zhang, Stephen L Buchwald
Affiliations

An improved palladium-catalyzed conversion of aryl and vinyl triflates to bromides and chlorides

Jun Pan et al. Org Lett. .

Abstract

A facile Pd-catalyzed conversion of aryl and vinyl triflates to aryl and vinyl halides (bromides and chlorides) is described. This method allows convenient access to a variety of aryl, heteroaryl, and vinyl halides in good to excellent yields and with greatly simplified conditions relative to our previous report.

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Figures

Figure 1
Figure 1
Biarylphosphine ligands.
Figure 2
Figure 2
Pd-Catalyzed Conversion of Triflates to Bromidesa a Reaction conditions: ArOTf (1.0 mmol), Pd2(dba)3 (1.5 mol %), L4 (4.5 mol %), KBr (2.0 mmol), KF (0.5 mmol), 1,4-dioxane (4 mL), 130 °C, 16 h. Isolated yields are based on an average of two runs.
Figure 3
Figure 3
Pd-Catalyzed Conversion of Triflates to Chloridesa a Reaction conditions: ArOTf (1.0 mmol), Pd2(dba)3 (1.5 mol %), L4 (4.5 mol %), KCl (2.0 mmol), KF (0.5 mmol), 1,4-dioxane (4 mL), 130 °C, 16 h. Isolated yields are based on an average of two runs.
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