Organocatalytic Deoxyhalogenation of Alcohols with Inorganic Halides

Abstract

Direct substitution of alcohols has been a popular topic in organic chemistry. Deoxyhalogenation of alcohols represents one of the most important transformations for accessing organic halides. However, a practical catalytic protocol with readily available, inexpensive, and stable inorganic halides is still unknown. Herein, we report an organocatalytic deoxyhalogenation of alcohols with inorganic halides, which avoids the employment of stoichiometric activators and organic halogenating reagents. Various alcohols are transformed to the corresponding organic bromides and iodides in good yield.

Catalyst-Free Trans-Selective Oxyiodination and Oxychlorination of Alkynes Employing N–X (Halogen) Reagents

“…Despite the significance of hydroalkoxylation [12,13], the scope of alkynes has mainly been focused on terminal alkynes, which lead to disubstituted enol esters/ethers. Introducing halogen atoms into organic molecules is an important step in organic synthesis [14][15][16][17][18][19][20][21], as halogen groups could serve as versatile synthetic handles for further transformations [22][23][24]. The oxyhalogenation of alkynes is a straightforward route to β-halogenated enol esters and ethers by simultaneously installing O-centered groups and halogen groups into C-C triple bonds.…”