14447-41-7Relevant articles and documents
Bordwell et al.
, p. 5298 (1968)
Bordwell,Jarvis
, p. 3585,3593 (1973)
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Jones,Damico
, p. 2273,2277 (1963)
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Visible light-mediated metal-free double bond deuteration of substituted phenylalkenes
Iakovenko, Roman,Hlavá?, Jan
supporting information, p. 440 - 446 (2021/01/28)
Various bromophenylalkenes were reductively photodebrominated by using 1,3-dimethyl-2-phenyl-1H-benzo-[d]imidazoline (DMBI) and 9,10-dicyanoanthracene. With deuterated DMBI analogs (the most effective was DMBI-d11), satisfactory to excellent isotopic yields were obtained. DMBI-d11 could also be regenerated from the reaction mixtures with a recovery rate of up to 50%. The combination of the photodebromination reaction with conventional methods for bromoalkene synthesis enables sequential monodeuteration of a double bond without the necessity of a metal catalyst. This journal is
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.