91388-35-1Relevant articles and documents
A Transient Directing Group Strategy Enables Enantioselective Multicomponent Organofluorine Synthesis
Liu, Zhonglin,Oxtoby, Lucas J.,Liu, Mingyu,Li, Zi-Qi,Tran, Van T.,Gao, Yang,Engle, Keary M.
supporting information, p. 8962 - 8969 (2021/07/01)
The vicinal fluorofunctionalization of alkenes represents an expedient strategy for converting feedstock olefins into valuable fluorinated molecules and as such has garnered significant attention from the synthetic community; however, current methods remain limited in terms of scope and selectivity. Here we report the site-selective palladium-catalyzed three-component coupling of alkenylbenzaldehydes, arylboronic acids, and N-fluoro-2,4,6-trimethylpyridinium hexafluorophosphate facilitated by a transient directing group. The synthetically enabling methodology constructs vicinal stereocenters with excellent regio-, diastereo-, and enantioselectivities, forging products that map onto bioactive compounds.
Cyclization reaction for the synthesis of polysubstituted naphthalenes in the presence of Au(I) precatalysts
Jagdale, Arun R.,Park, Jong Hyub,Youn, So Won
experimental part, p. 7204 - 7215 (2011/10/17)
Au(I)-catalyzed cyclization of alkenyl carbonyl compounds leading to a variety of substituted naphthalenes has been developed. This process exploits a dual function of the Au(I) catalyst: (1) the oxophilic nature of the Au(I) catalyst, counterintuitive to the π-acidic reactivities generally associated with Au catalysts, and (2) olefin isomerization supported by the outcome of isotope scrambling experiments. It cannot be completely excluded that TfOH is a true operative catalyst in this protocol. In view of the practicality, the unnecessity of isomerically pure starting material in this reaction is particularly attractive and valuable.
Manganese-catalyzed substitution of activated aryl halides (X = Cl, Br and F) and aryl ethers by organomagnesium reagents
Cahiez, Gerard,Lepifre, Franck,Ramiandrasoa, Parfait
, p. 2138 - 2144 (2007/10/03)
In the presence of manganese chloride (10%), Grignard reagents readily react in THF with aryl bromides, chlorides and even fluorides, as well as aryl methyl ethers bearing in the ortho- or para-position an electron withdrawing activating group (CN, CH=NR, oxazoline). Aryl and N- or S- alkylmagnesium halides have been used successfully. The reaction is performed under mild conditions (0 °C to room temperature, 30 minutes to 24 hours) and leads to cross-coupling products in good yields.