16324-15-5Relevant articles and documents
Wacker-Type Oxidation Using an Iron Catalyst and Ambient Air: Application to Late-Stage Oxidation of Complex Molecules
Liu, Binbin,Jin, Fengli,Wang, Tianjiao,Yuan, Xiaorong,Han, Wei
supporting information, p. 12712 - 12717 (2017/09/11)
A practical and general iron-catalyzed Wacker-type oxidation of olefins to ketones is presented, and it uses ambient air as the sole oxidant. The mild oxidation conditions enable exceptional functional-group tolerance, which has not been demonstrated for any other Wacker-type reaction to date. The inexpensive and nontoxic reagents [iron(II) chloride, polymethylhydrosiloxane, and air] can, therefore, also be employed to oxidize complex natural-product-derived and polyfunctionalized molecules.
Zinc-Mediated Chain Extension of β-Keto Phosphonates
Verbicky, Christopher A.,Zercher, Charles K.
, p. 5615 - 5622 (2007/10/03)
A variety of β-keto phosphonates can be converted to γ-keto phosphonates through reaction with ethyl(iodomethyl)zinc. The presence of α-alkyl substituents, Lewis basic functionality, and modestly acidic NH-protons are accommodated in substrates of this reaction. Chain extension of β-keto phosphonates that contained olefinic functionality proceeded more quickly than cyclopropanation; however, it was not possible to effect the chain extension to the exclusion of cyclopropane formation. A primary reason for this imperfect chemoselectivity appears to be the slow chain extension of β-keto phosphonates. Nevertheless, the simplicity, the scope, and efficiency of this method serve to make it an attractive alternative to the established methods for γ-keto phosphonate formation.
