5239-82-7Relevant articles and documents
Rhodes,Vargas
, p. 4077,4078 (1973)
Oxidation of Alkynyl Boronates to Carboxylic Acids, Esters, and Amides
Li, Chenchen,Li, Ruoling,Zhang, Bing,Zhao, Pei,Zhao, Wanxiang
supporting information, p. 10913 - 10917 (2020/05/25)
A general efficient protocol was developed for the synthesis of carboxylic acids, esters, and amides through oxidation of alkynyl boronates, generated directly from terminal alkynes. This protocol represents the first example of C(sp)?B bond oxidation. This approach displays a broad substrate scope, including aryl and alkyl alkynes, and exhibits excellent functional group tolerance. Water, primary and secondary alcohols, and amines are suitable nucleophiles for this transformation. Notably, amino acids and peptides can be used as nucleophiles, providing an efficient method for the synthesis and modification of peptides. The practicability of this methodology was further highlighted by the preparation of pharmaceutical molecules.
Direct Carbon Isotope Exchange through Decarboxylative Carboxylation
Kingston, Cian,Wallace, Michael A.,Allentoff, Alban J.,Degruyter, Justine N.,Chen, Jason S.,Gong, Sharon X.,Bonacorsi, Samuel,Baran, Phil S.
supporting information, p. 774 - 779 (2019/01/14)
A two-step degradation-reconstruction approach to the carbon-14 radiolabeling of alkyl carboxylic acids is presented. Simple activation via redox-active ester formation was followed by nickel-mediated decarboxylative carboxylation to afford a range of complex compounds with ample isotopic incorporations for drug metabolism and pharmacokinetic studies. The practicality and operational simplicity of the protocol were demonstrated by its use in an industrial carbon-14 radiolabeling setting.