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Oxidation of Alkynyl Boronates to Carboxylic Acids, Esters, and Amides
Author(s) -
Li Chenchen,
Zhao Pei,
Li Ruoling,
Zhang Bing,
Zhao Wanxiang
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202000988
Subject(s) - chemistry , nucleophile , functional group , primary (astronomy) , alkyl , combinatorial chemistry , substrate (aquarium) , aryl , organic chemistry , carboxylic acid , amino acid , scope (computer science) , catalysis , biochemistry , physics , oceanography , astronomy , geology , polymer , computer science , programming language
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.