Only second to the dihalogens, hydrogen halides are the most atom efficient source of halogenation. However, hydrogen halides are gases at ambient temperature so their utility is limited due to challenges in handling of gases. We present the preparation of new highly concentrated and bench stable organic solutions of these HX molecules that have special reactivity with alkenes and alkynes. These solutions take advantage of the strong hydrogen bond basicity pK<sub>BHX</sub> of the solvent 1,3-dimethyl-3,4,5,6-tetrahydro-2(1<i>H</i>)-pyrimidinone (DMPU) to form stable complex with HX molecules. These new organic-based solution of hydrogen halides have been applied in a metal free hydrobromination of alkynes and a homogenous gold-catalyzed hydrochlorination of alkynes.

Investigating the reactivity of HCl/DMPU and HBr/DMPU reagents with unsaturated systems

254th National Meeting (2017)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.