Download PDF by Arimasa Matsumoto: Iron-Catalyzed Synthesis of Fused Aromatic Compounds via C–H

By Arimasa Matsumoto

ISBN-10: 4431549277

ISBN-13: 9784431549277

ISBN-10: 4431549285

ISBN-13: 9784431549284

Iron catalysts in natural synthesis are strongly widespread simply because iron is non-toxic, low-cost and the main ample transition steel within the earth, even though their use remains to be constrained in comparison with that of infrequent, priceless metals similar to palladium, ruthenium and rhodium. This thesis describes the 1st sensible instance of iron catalysis within the carbon–hydrogen bond activation response to synthesized fused fragrant ring compounds. by utilizing a distinct mix of iron catalyst and dichloride oxidant, quite a few form of naphthalene and phenanthrene derivatives have been synthesized through annulation response with alkynes together with direct C–H bond activation technique. This fulfillment opens the hot hazard of low-valent iron catalysis and expands man made equipment for a sustainable society.

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Extra resources for Iron-Catalyzed Synthesis of Fused Aromatic Compounds via C–H Bond Activation

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42 3,10-dimethyl-9-phenylphenanthrene and 3,9-dimethyl-10-phenylphenanthrene (Eq. 5): obtained in 93 % yield (55:45 mixture of isomers by NMR) as a colorless oil. 7 Experimental Part 43 gel-permeation chromatography (GPC). The structure was determined by 2DNMR (COSY and NOESY) of the mixture. 75H). 2. GC MS (EI) m/z (relative intensity): Major isomer: 283 (23), 282 (M+, 100), 267 (30), 265 (25), 252 (17). Minor isomer: 283 (24), 282 (M+, 100), 267 (28), 265 (25), 252 (16). Anal. 43. 68. 1 mg, 60 %), after quenching with D2O.

The water content of the solvent was confirmed by a Karl-Fischer moisture titrator to be less than 20 ppm. 1-chloro-4-(phenylethynyl)benzene, 1-bromo4-(phenylethynyl)benzene, 1-methoxy-4-(phenylethynyl)benzene, N,N-dimethyl4-(phenylethynyl)aniline, and (E)-but-1-en-3-yne-1,4-diyldibenzene were prepared by Sonogashira coupling [20] of phenylacetylene and the corresponding iodide or bromide (PdCl2(PPh3)2/CuI/NEt3) and purified by recrystallization from EtOH. 3,3,3-trifluoro-1-phenylpropyne was prepared according literature [21].

5 (2C). GC MS (EI) m/z (relative intensity): 374 (31), 373 (M+, 100). 7 Experimental Part 37 Anal. 75. 52. 4, entry 6): A mixture of the enyne and Grignard reagent in ether was slowly added over 10 min. The title compound was obtained in 79 % yield as a colorless solid. 8 °C. IR (powder): cm-1 3065, 3020, 1599, 1574, 1486, 1442, 1418, 1069, 1043, 1027, 966, 859, 762, 741, 724, 693, 616. 6 Hz, 1H). 4. GC MS (EI) m/z (relative intensity): 357 (31), 356 (M+, 100), 279 (33), 265 (43), 207 (12), 91 (26), 78 (64).

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Iron-Catalyzed Synthesis of Fused Aromatic Compounds via C–H Bond Activation by Arimasa Matsumoto


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