In 2022,Huang, Mingming; Hu, Jiefeng; Krummenacher, Ivo; Friedrich, Alexandra; Braunschweig, Holger; Westcott, Stephen A.; Radius, Udo; Marder, Todd B. published an article in Chemistry – A European Journal. The title of the article was 《Base-Mediated Radical Borylation of Alkyl Sulfones》.Reference of tert-Butyl 4-hydroxypiperidine-1-carboxylate The author mentioned the following in the article:
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. In the experiment, the researchers used tert-Butyl 4-hydroxypiperidine-1-carboxylate(cas: 109384-19-2Reference of tert-Butyl 4-hydroxypiperidine-1-carboxylate)
tert-Butyl 4-hydroxypiperidine-1-carboxylate(cas:109384-19-2) is a 4-hydroxypyridine with a boc protecting group used in the preparation of neurologically active agents and other pharmaceutical compounds.Reference of tert-Butyl 4-hydroxypiperidine-1-carboxylate
Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem