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Readily Accessible Bulky Iron Catalysts exhibiting Site Selectivity in the Oxidation of Steroidal Substrates

http://dugi.udg.edu/item/http:@@@@hdl.handle.net@@10256@@12492

El mateix article està publicat a l’edició alemanya d’Angewandte Chemie (ISSN 0044-8249 EISSN:1521-3757), 2016, vol.128, núm. 19, p.5870-5873. DOI http://dx.doi.org/10.1002/ange.201600785

Bulky iron complexes are described that catalyze the site-selective oxidation of alkyl C-H bonds with hydrogen peroxide under mild conditions. Steric bulk at the iron center is introduced by appending trialkylsilyl groups at the meta-position of the pyridines in tetradentate aminopyridine ligands, and this effect translates into high product yields, an enhanced preferential oxidation of secondary over tertiary C-H bonds, and the ability to perform site-selective oxidation of methylenic sites in terpenoid and steroidal substrates. Unprecedented site selective oxidation at C6 and C12 methylenic sites in steroidal substrates is shown to be governed by the chirality of the catalysts

Financial support for this work was provided by the European Commission (ERC2009-StG-239910 to M.C.), the Spanish Ministry of Science (CTQ2012-37420-C02-01/BQU to M.C., and Generalitat de Catalunya (SGR862 and ICREA Academia Award to M.C.)

Wiley