Visible-light-induced decarboxylative and deboronative reactions using two-molecule organic photoredox catalysts, namely, phenanthrene (Phen) and biphenyl (BP), as electron donors and 9-cyano-10-methoxycarbonylanthracene 1a as an electron acceptor were achieved. The high solubility of 1a significantly improved the reaction efficiency and product yield. In addition, the facile tuning of the oxidation potential of the electron-donor molecule via the replacement of Phen with BP enabled the application of the two-molecule photoredox system to a wide range of substrates.
A new
strategy for the synthesis of 23-, 25-, 27-, and
29-membered (Z)-selective unsaturated and saturated
macrocyclic lactones from commercially available 16- and 17-membered
macrocyclic lactones and bromoalcohols by Wittig reaction, Yamaguchi
macrolactonization, and photoinduced decarboxylative radical macrolactonization
is described. The position of the unsaturated part in the macrocyclic
lactones can be controlled by changing the number of carbons in the
starting materials. This protocol can provide facile access to the
desired large-ring (Z)-selective unsaturated and
saturated macrocyclic lactones from simple starting materials.
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