1097200-59-3Relevant academic research and scientific papers
Catalytic Allylic Oxidation of Cyclic Enamides and 3,4-Dihydro-2H-Pyrans by TBHP
Yu, Yang,Humeidi, Ranad,Alleyn, James R.,Doyle, Michael P.
, p. 8506 - 8513 (2017)
Allylic oxidation of heteroatom substituted cyclic alkenes by tert-butyl hydroperoxide (70% TBHP in water) using catalytic dirhodium caprolactamate [Rh2(cap)4] forms enone products with a variety of 2-substituted cyclic enamides and 3,4-dihyro-2H-pyrans. These reactions occur under mild reaction conditions, are operationally convenient to execute, and are effective for product formation with as low as 0.25 mol% catalyst loading. With heteroatom stabilization of the intermediate allylic free radical two sites for oxidative product formation are possible, and the selectivity of the oxidative process varies with the heteroatom when R = H. Cyclic enamides produce 4-piperidones in good yields when R = alkyl or aryl, but oxidation of 2H-pyrans also gives alkyl cleavage products. Alternative catalysts for TBHP oxidations show comparable selectivities but give lower product yields.
Enol phosphinates and phosphonates: Practical electrophiles for cross-coupling strategies
Steel, Patrick G.,Woods, Tom M.
experimental part, p. 3897 - 3904 (2010/03/24)
Enol phosphinates and phosphonates can be readily prepared from simple lactams in high yields and are both stable and storable. Both these substrates can be employed successfully in homogeneous Suzuki-Miyaura and Stille cross-couplings protocols. Additionally, the phosphonate group can be immobilised on a phenol-on-polystyrene resin and utilised in a simple diversity linker strategy in which the coupled product is cleaved from the resin under Suzuki-Miyaura cross-coupling conditions. Georg Thieme Verlag Stuttgart.
Phosphinates as new electrophilic partners for cross-coupling reactions
Guo, Jun,Harling, John D.,Steel, Patrick G.,Woods, Tom M.
experimental part, p. 4053 - 4058 (2009/06/28)
The use of enol phosphinates as electrophiles for cross-coupling reactions has been explored. Both boronic acids (Suzuki-Miyaura reaction) and stannanes (Stille reaction) couple efficiently with lactam derived phosphinates. The 2008 Royal Society of Chemi
