4272-12-2Relevant articles and documents
Ligand-Enabled Monoselective β-C(sp3)-H Acyloxylation of Free Carboxylic Acids Using a Practical Oxidant
Fan, Zhoulong,Herron, Alastair N.,Yu, Jin-Quan,Zhuang, Zhe
supporting information, p. 6769 - 6776 (2020/04/30)
The development of C-H activation reactions that use inexpensive and practical oxidants remains a significant challenge. Until our recent disclosure of the β-lactonization of free aliphatic acids, the use of peroxides in C-H activation reactions directed by weakly coordinating native functional groups was unreported. Herein, we report C(sp3)-H β-acetoxylation and γ-, δ-, and ?-lactonization reactions of free carboxylic acids enabled by a novel cyclopentane-based mono-N-protected β-amino acid ligand. Notably, tert-butyl hydrogen peroxide is used as the sole oxidant for these reactions. This reaction has several key advantages over other C-H activation protocols: (1) exclusive monoselectivity was observed in the presence of two α-methyl groups; (2) aliphatic carboxylic acids containing α-hydrogens are compatible with this protocol; (3) lactonization of free acids, affording γ-, δ-, or ?-lactones, has been achieved for the first time.
A Cooperative Strategy for the Highly Selective Intermolecular Oxycarbonylation Reaction of Alkenes using a Palladium Catalyst
Li, Ming,Yu, Feng,Qi, Xiaoxu,Chen, Pinhong,Liu, Guosheng
supporting information, p. 13843 - 13848 (2016/10/26)
A novel method for intermolecular functionalization of terminal and internal alkenes has been designed. The electrophilic reagent, hypervalent iodine, plays a key role in this process by activating the alkene C=C bond for nucleophilic addition of the palladium catalyst. This process generates an iodonium-containing palladium species which undergoes CO insertion. The new approach, intermolecular oxycarbonylaton reactions of alkenes, has been achieved and carried out under mild reaction conditions to produce the corresponding β-oxycarbonylic acids with excellent efficiencies and levels of regio- and diastereoselectivity.
CARBONYLATION OF ETHYLENICALLY UNSATURATED COMPOUNDS
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Paragraph 0234-0236, (2016/10/09)
PROBLEM TO BE SOLVED: To provide a process for the carbonylation of ethylenically unsaturated compounds including vinyl esters and a process for the production of 3-hydroxypropanoate esters or 3-hydroxypropanoic acids. SOLUTION: The process comprises reacting the compound with carbon monoxide in the presence of a source of hydroxyl groups and of a catalyst system. The catalyst system is obtainable by combining: (a) a metal of Group 8, 9 or 10 or a compound thereof: and (b) a bidentate ligand of general formula (I): X1(X2)-Q2-A-R-B-Q1-X3(X4). COPYRIGHT: (C)2015,JPOandINPIT
