91335-82-9Relevant academic research and scientific papers
The catalytic cleavage of carbon-carbon double bond in polychloroprene induced by Schwartz's reagent via chlorine self-assisted β-alkyl elimination mechanism
Gu, Yang,Ye, Lin,Lin, Fei,Lin, Yichao,Tang, Tao,Ma, Li
, p. 24 - 30 (2019)
The carbon-carbon double bonds (C[dbnd]C) in polychloroprene (PCP) was broken down by Schwartz's reagent ([Cp2ZrClH]n) under mild conditions. The reaction mechanism for cleaving C[dbnd]C bonds in PCP was studied in detail. It was found that the cleavage pathway was chlorine self-assisted β-alkyl elimination reaction, namely, β-alkyl elimination was promoted while chlorine in PCP was eliminated by releasing Cp2ZrCl2. The molecular weights of chain-scission products were controlled ranging from starting molecular weights of PCP to 0.2 kg mol?1; at the same time, microstructures of chain-scission products were similar to chain structures of original PCP. In addition, chain-scission products could be chain-end functionalized by electrophiles quenching chain scission reaction. More importantly, efficient catalytic chain cleavage was achieved under the synergistic effect of [Cp2ZrClH]n with both LiH and H2.
Cyclic (Alkyl)(amino)carbene Ligands Enable Cu-Catalyzed Markovnikov Protoboration and Protosilylation of Terminal Alkynes: A Versatile Portal to Functionalized Alkenes**
Bertrand, Guy,Engle, Keary M.,Gao, Yang,Grotjahn, Douglas B.,Jazzar, Rodolphe,Junor, Glen P.,Kang, Taeho,Kendrick, Aaron,Yazdani, Sima
supporting information, p. 19871 - 19878 (2021/08/13)
Regioselective hydrofunctionalization of alkynes represents a straightforward route to access alkenyl boronate and silane building blocks. In previously reported catalytic systems, high selectivity is achieved with a limited scope of substrates and/or rea
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.
