期刊
ADVANCED SYNTHESIS & CATALYSIS
卷 357, 期 16-17, 页码 3687-3695出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201500483
关键词
decatungstate salts; flow reactions; hydrogen atom transfer; photocatalysis; waste minimization
A set of atom economical radical conjugate addition reactions of alkyl and acyl radicals onto electron-poor olefins or diisopropyl azodicarboxylate has been carried out on a multi-gram scale under continuous flow conditions. The process is based on the use of the inorganic photocatalyst tetrabutylammonium decatungstate (TBADT), which is capable to activate selectively a variety of C-H bonds in different substrates, including aldehydes, amides, ethers and alkanes. A wide range of synthetic targets has been synthesized according to this procedure, including 1,4-difunctionalized derivatives (e.g., 1,4-diketones or keto esters). All the reactions have been carried out in a meso-scale flow photo-reactor consisting in coils of UV-transparent FEP tubing (fluorinated ethylene propylene) wrapped around a water-cooled 500W medium pressure mercury vapor lamp. The use of such a photochemical apparatus caused a reduction of the residence time, a notable increase of the STY (space time yield) and of the productivity values with respect to those measured for the corresponding batch processes. often leading to an improvement of the overall sustainability of the process (process mass intensity PMI values down to 10 kg kg(-1)).
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