A sequence of a Baeyer-Villiger oxidation and a Lewis acid-promoted reduction of the resulting formate with Et SiH enabled the metal-free formal decarbonylation of tertiary and secondary aliphatic aldehydes. The new methodology mimics the biosynthetic decarbonylation pathway through oxidative C-C bond cleavage rather than the C(O)-H bond activation known from conventional Tsuji-Wilkinson-type reactions. The substrate scope is complementary to existing transition-metal-catalyzed protocols.
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http://dx.doi.org/10.1002/chem.201902082 | DOI Listing |
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