55539-39-4Relevant 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.
One-pot synthesis of sulfones via Ni(II)-catalyzed sulfonylation of boronic acids, Na2S2O5 and benzylic ammonium salts
Zhu, Haibo,Liu, Yishuai,Zhang, Yingying,Yang, Liu,Meng, Jia,Li, Qian,Gong, Bozhen,Xie, Zongbo,Le, Zhang-Gao
, (2021/03/08)
A one-pot nickel-catalyzed synthesis of (hetero)aryl alkyl sulfones from readily available boronic acids, sodium metabisulfite and benzylic ammonium salts as electrophiles is described. This general and efficient synthetic process is of broad scope, occurs in two steps, and delivers structural diverse sulfones, and the intermediate sulfinate is isolated. The transformation exhibits application of benzylic ammonium salts as novel electrophiles for direct insertion of SO2 as a novel area to be investigated.
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.
