2930-80-5Relevant articles and documents
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Kevill,D.N.,Weitl,F.L.
, p. 2633 - 2634 (1967)
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Transition metal- And light-free radical borylation of alkyl bromides and iodides using silane
Mo, Fanyang,Sun, Beiqi,Zheng, Sihan
supporting information, p. 5674 - 5677 (2021/06/16)
We report operationally simple and neutral conditions for borylation of alkyl bromides and iodides to alkyl boronic esters under transition metal- and light-free conditions. A series of substrates with a wide range of functional groups were effectively transformed into the borylation products in moderate to good yields. Mechanistic studies, including radical clock experiments and DFT calculations, gave detailed insight into the radical borylation process.
A mild method for the replacement of a hydroxyl group by halogen: 2. unified procedure and stereochemical studies
Gati, Wafa,Munyemana, Fran?ois,Colens, Alain,Srour, Aladdin,Dufour, Mathilde,Vardhan Reddy, K. Harsha,Téchy, Brigitte,Rosse, Gérard,Schweiger, Ed,Qiao, Qi,Ghosez, Léon
, (2020/08/19)
N,N-Dimethyl- and N,N-diisopropyl-1-halo-2-methyl-l-propenylamines are readily available reagents for the mild deoxyhalogenation of alcohols and hydroxyacids. In this study we showed that the reactivity of the reagents can be tuned by varying the size of the alkyl groups on the reagents: the replacement of methyl by isopropyl groups led to a significant increase of reactivity. We then described a unified procedure for all deoxyhalogenations using the readily available α-chloroenamines as reagents with (bromination, iodination) or without (chlorination) an alkaline bromide or iodide. Finally, we showed that deoxyhalogenation reactions of secondary alcohols were highly stereospecific and generally occurred with inversion of configuration.
Synthesis of Nitrile-Bearing Quaternary Centers by an Equilibrium-Driven Transnitrilation and Anion-Relay Strategy
Alazet, Sébastien,West, Michael S.,Patel, Purvish,Rousseaux, Sophie A. L.
supporting information, p. 10300 - 10304 (2019/07/04)
The efficient preparation of nitrile-containing building blocks is of interest due to their utility as synthetic intermediates and their prevalence in pharmaceuticals. As a result, significant efforts have been made to develop methods to access these motifs which rely on safer and non-toxic sources of CN. Herein, we report that 2-methyl-2-phenylpropanenitrile is an efficient, non-toxic, electrophilic CN source for the synthesis of nitrile-bearing quaternary centers by a thermodynamic transnitrilation and anion-relay strategy. This one-pot process leads to nitrile products resulting from the gem-difunctionalization of alkyl lithium reagents.