Directed alkyne oxyhalogenation pre-print online

Over the years, we’ve found that translating lessons learned in alkene difunctionalization to alkyne substrates is not as straightforwards as it seems, owing to unique reactivity profiles of alkyl- versus alkenylpalladium species. In our most recent collaboration with the Shi group from Zhejiang University and the Lan group from Zhengzhou University, we show that use of the 2-(pyridin-2-yl)isopropyl (PIP) amide directing group enables regio- and stereoselective oxyhalogenation of alkynes. The alkenyl halide products can be readily diversified via cross-coupling to access an array of tetrasubstituted alkene products. Congrats to Mingyu, Juntao, and Raul (Scripps Research); Tao (Zhengzhou U), Yi and Ye-Qiang (Zhejiang U) for an excellent study.

For a link to the ChemRxiv pre-print, click here: