772-13-4Relevant articles and documents
A Molecular Iron-Based System for Divergent Bond Activation: Controlling the Reactivity of Aldehydes
Chatterjee, Basujit,Jena, Soumyashree,Chugh, Vishal,Weyhermüller, Thomas,Werlé, Christophe
, p. 7176 - 7185 (2021/06/30)
The direct synthesis of amides and nitriles from readily available aldehyde precursors provides access to functional groups of major synthetic utility. To date, most reliable catalytic methods have typically been optimized to supply one product exclusively. Herein, we describe an approach centered on an operationally simple iron-based system that, depending on the reaction conditions, selectively addresses either the C=O or C-H bond of aldehydes. This way, two divergent reaction pathways can be opened to furnish both products in high yields and selectivities under mild reaction conditions. The catalyst system takes advantage of iron's dual reactivity capable of acting as (1) a Lewis acid and (2) a nitrene transfer platform to govern the aldehyde building block. The present transformation offers a rare control over the selectivity on the basis of the iron system's ionic nature. This approach expands the repertoire of protocols for amide and nitrile synthesis and shows that fine adjustments of the catalyst system's molecular environment can supply control over bond activation processes, thus providing easy access to various products from primary building blocks.
Primary fatty acid amide preparation method
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Paragraph 0273-0275, (2018/10/19)
The present invention provides a primary fatty acid amide preparation method. According to the present invention, under the action of a single auxiliary agent phosphine-containing transition metal catalyst or a combined auxiliary agent comprising a phosphine-free transition metal catalyst and a phosphine-containing ligand, terminally substituted olefin or cyclo-olefin, carbon monoxide and an ammonium salt are subjected to a hydrogen carboamidation reaction so as to prepare the primary fatty acid amide compound in one step; the raw material and the catalyst of the reaction are inexpensive and easy to obtain, and the synthesis process is simple, such that the synthesis cost is substantially reduced; the preparation method has characteristics of mild reaction condition and high yield, and issuitable for industrial production; and the raw material and the catalyst of the reaction are clean, non-toxic and low environment pollution.
Palladium-Catalyzed α,β-Dehydrogenation of Esters and Nitriles
Chen, Yifeng,Romaire, Justin P.,Newhouse, Timothy R.
supporting information, p. 5875 - 5878 (2015/05/27)
A highly practical and general palladium-catalyzed methodology for the α,β-dehydrogenation of esters and nitriles is reported. Generation of a zinc enolate or (cyanoalkyl)zinc species followed by the addition of an allyl oxidant and a palladium catalyst results in synthetically useful yields of α,β-unsaturated esters, lactones, and nitriles. Preliminary mechanistic investigations are consistent with reversible β-hydride elimination and turnover-limiting, propene-forming reductive elimination.
