91110-68-8Relevant articles and documents
Base-Mediated Radical Borylation of Alkyl Sulfones
Huang, Mingming,Hu, Jiefeng,Krummenacher, Ivo,Friedrich, Alexandra,Braunschweig, Holger,Westcott, Stephen A.,Radius, Udo,Marder, Todd B.
supporting information, (2021/12/02)
A practical and direct method was developed for the production of versatile alkyl boronate esters via transition metal-free borylation of primary and secondary alkyl sulfones. The key to the success of the strategy is the use of bis(neopentyl glycolato) diboron (B2neop2), with a stoichiometric amount of base as a promoter. The practicality and industrial potential of this protocol are highlighted by its wide functional group tolerance, the late-stage modification of complex compounds, no need for further transesterification, and operational simplicity. Radical clock, radical trap experiments, and EPR studies were conducted which show that the borylation process involves radical intermediates.
Manganese-Catalyzed Acceptorless Dehydrogenative Coupling of Alcohols with Sulfones: A Tool to Access Highly Substituted Vinyl Sulfones
Barman, Milan K.,Maji, Biplab,Waiba, Satyadeep
, p. 973 - 982 (2021/08/24)
The development of first-row-transition-metal catalysts that can match with the reactivities of the noble metals is considered to be challenging yet very much a desirable goal in homogeneous catalysis. It has become even more fascinating to develop processes where these metals show a unique reactivity and selectivity than their higher congeners. Herein, we report on the catalytic activity of a pincer complex of the abundant earth metal manganese for an unprecedented acceptorless dehydrogenative coupling of alkyl sulfones with alcohols. Thus, highly functionalized vinyl sulfones were obtained in moderate to good yields. Both benzylic and aliphatic alcohols could be utilized, and several functional groups including bromides and iodides are tolerated under the reaction conditions. The reaction is environmentally benign, producing dihydrogen and water as byproducts. Preliminary mechanistic experiments involving kinetic, deuterium-labeling, and NMR experiments were performed.
Deep Eutectic Solvents as Reaction Media for the Palladium-Catalysed C?S Bond Formation: Scope and Mechanistic Studies
Marset, Xavier,Guillena, Gabriela,Ramón, Diego J.
supporting information, p. 10522 - 10526 (2017/08/10)
A unique jigsaw catalytic system based on deep eutectic solvents and palladium nanoparticles where C?S bonds are formed from aryl boronic acids and sodium metabisulfite, is introduced. The functionalization step is compatible with a broad spectrum of reagents such as nucleophiles, electrophiles or radical scavengers. This versatile approach allows the formation of different types of products in an environmentally friendly medium by selecting the components of the reaction, which engage one with another as pieces in a jigsaw. This simple procedure avoids the use of toxic volatile organic solvents allowing the formation of complex molecules in a one-pot reaction under mild conditions. Despite the fact that only 1 mol % of metal loading is used, the recyclability of the catalytic system is possible. Kinetic experiments were performed and the reaction order for all reagents, catalyst and ligand was determined. The obtained results were compared to palladium nanocrystals of different known shapes in order to shed some light on the properties of the catalyst.
