18410-58-7Relevant articles and documents
SOME GROUP IVB DERIVATIVES OF 1,6-METHANOANNULENE. SYNTHESIS, SUBSTITUENT EFFECTS AND REACTIVITY
Kitching, William,Olszowy, Henry A.,Schott, Inge,Adcock, William,Cox, D. P.
, p. 269 - 284 (1986)
Certain Group IVB derivatives of 1,6-methanoannulene have been synthesised, and their 13C nuclear magnetic resonance spectra recorded and assigned, to provide a measure of the substituent effects exerted by metalloid-containing groups in this non-benzenoid aromatic system.Comparisons are made with the corresponding naphthalene and some anthracene derivatives.Protiodemetallations of a number of arylsilanes and -stannanes have been examined, and in protiodestannyletion by CH3CO2H/dioxane at 27 deg C (an electrophilic aromatic substitution) the α- (or 2-) posititon of 1,6-methanoannulene is ca. 35 times as reactive as the α (or 1-) position of naphthalene, whereas in protiodesilylation by CF3CO2H/CH3CO2H at 27 deg C it is ca. 700 times the more reactive.
Water and Sodium Chloride: Essential Ingredients for Robust and Fast Pd-Catalysed Cross-Coupling Reactions between Organolithium Reagents and (Hetero)aryl Halides
Dilauro, Giuseppe,Quivelli, Andrea Francesca,Vitale, Paola,Capriati, Vito,Perna, Filippo Maria
supporting information, p. 1799 - 1802 (2019/01/25)
Direct palladium-catalysed cross-couplings between organolithium reagents and (hetero)aryl halides (Br, Cl) proceed fast, cleanly and selectively at room temperature in air, with water as the only reaction medium and in the presence of NaCl as a cheap additive. Under optimised reaction conditions, a water-accelerated catalysis is responsible for furnishing C(sp3)–C(sp2), C(sp2)–C(sp2), and C(sp)–C(sp2) cross-coupled products, in competition with protonolysis, within a reaction time of 20 s, in yields of up to 99 %, and in the absence of undesired dehalogenated/homocoupling side products even when challenging secondary organolithiums serve as the starting material. It is worth noting that the proposed protocol is scalable and the catalyst and water can easily and successfully be recycled up to 10 times, with an E-factor as low as 7.35.
Nickel-Catalyzed Csp2-Csp3 Bond Formation via C-F Bond Activation
Ho, Yee Ann,Leiendecker, Matthias,Liu, Xiangqian,Wang, Chengming,Alandini, Nurtalya,Rueping, Magnus
supporting information, p. 5644 - 5647 (2018/09/12)
A nickel-catalyzed cross coupling of aryl fluorides via C-F bond activation has been developed. The alkylation method allows selective replacement of aryl fluorides by alkyl groups and enables the synthesis of diverse and otherwise difficult to access scaffolds in good yields.
