103786-19-2Relevant articles and documents
Orthogonally protected 1,2-diols from electron-rich alkenes using metal-free olefin syn-dihydroxylation
Colomer, Ignacio,Barcelos, Rosimeire Coura,Christensen, Kirsten E.,Donohoe, Timothy J.
, p. 5880 - 5883 (2016)
A new method for the stereoselective metal-free syn-dihydroxylation of electron-rich olefins is reported, involving reaction with TEMPO/IBX in trifluoroethanol (TFE) or hexafluoroisopropanol (HFIP) and the addition of a suitable nucleophile. Orthogonally
A transition-metal-free Heck-type reaction between alkenes and alkyl iodides enabled by light in water
Liu, Wenbo,Li, Lu,Chen, Zhengwang,Li, Chao-Jun
supporting information, p. 6170 - 6174 (2015/06/08)
A transition-metal-free coupling protocol between various alkenes and non-activated alkyl iodides has been developed by using photoenergy in water for the first time. Under UV irradiation and basic aqueous conditions, various alkenes efficiently couple with a wide range of non-activated alkyl iodides. A tentative mechanism, which involves an atom transfer radical addition process, for the coupling is proposed.
Analyzing site selectivity in Rh2(esp)2-catalyzed intermolecular C-H amination reactions
Bess, Elizabeth N.,Deluca, Ryan J.,Tindall, Daniel J.,Oderinde, Martins S.,Roizen, Jennifer L.,Du Bois,Sigman, Matthew S.
supporting information, p. 5783 - 5789 (2014/05/06)
Predicting site selectivity in C-H bond oxidation reactions involving heteroatom transfer is challenged by the small energetic differences between disparate bond types and the subtle interplay of steric and electronic effects that influence reactivity. Herein, the factors governing selective Rh 2(esp)2-catalyzed C-H amination of isoamylbenzene derivatives are investigated, where modification to both the nitrogen source, a sulfamate ester, and substrate are shown to impact isomeric product ratios. Linear regression mathematical modeling is used to define a relationship that equates both IR stretching parameters and Hammett σ+ values to the differential free energy of benzylic versus tertiary C-H amination. This model has informed the development of a novel sulfamate ester, which affords the highest benzylic-to-tertiary site selectivity (9.5:1) observed for this system.