951887-60-8Relevant articles and documents
Iridium-Catalyzed Hydrochlorination and Hydrobromination of Alkynes by Shuttle Catalysis
Yu, Peng,Bismuto, Alessandro,Morandi, Bill
supporting information, p. 2904 - 2910 (2020/01/25)
Described herein are two different methods for the synthesis of vinyl halides by a shuttle catalysis based iridium-catalyzed transfer hydrohalogenation of unactivated alkynes. The use of 4-chlorobutan-2-one or tert-butyl halide as donors of hydrogen halides allows this transformation in the absence of corrosive reagents, such as hydrogen halides or acid chlorides, thus largely improving the functional-group tolerance and safety profile of these reactions compared to the state-of-the-art. This method has granted access to alkenyl halide compounds containing acid-sensitive groups, such as tertiary alcohols, silyl ethers, and acetals. The synthetic value of those methodologies has been demonstrated by gram-scale synthesis where low catalyst loading was achieved.
A Chlorinating Reagent Yields Vinyl Chlorides with High Regioselectivity under Heterogeneous Gold Catalysis
Liang, Shengzong,Ebule, Rene,Hammond, Gerald B.,Xu, Bo
supporting information, p. 4524 - 4527 (2017/09/11)
A novel chlorinating reagent with a high concentration of HCl has enabled the highly regioselective hydrochlorination of unactivated alkynes using a commercial nanogold catalyst. No overchlorination or hydration products were formed, and various functional groups were tolerated. This hydrochlorination method could be conducted under open air.
