Petasis three-component reaction accelerated by trifluoroacetic acid: synthesis of indoline-derived glycines

The Petasis boron–Mannich reaction, simply referred to as the Petasis reaction, is a powerful multicomponent coupling reaction of a boronic acid, an amine, and a carbonyl derivative. Highly functionalized amines with multiple stereogenic centers can be efficiently accessed via the Petasis reaction with high levels of both diastereoselectivity and enantioselectivity. By drawing attention to examples reported in the past 8 years, this Review demonstrates the breadth of the reactivity and synthetic applications of Petasis reactions in several frontiers: the expansion of the substrate scope in the classic three-component process; nonclassic Petasis reactions with additional components; Petasis-type reactions with noncanonical substrates, mechanism, and products; new asymmetric versions assisted by chiral catalysts; combinations with a secondary or tertiary transformation in a cascade- or sequence-specific manner to access structurally complex, natural-product-like heterocycles; and the synthesis of polyhydroxy alkaloids and biologically interesting molecules.

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“…The obtained arylacetic acids 10 were studied as precursors for the synthesis of potential HDAC inhibitors (Scheme 4). 57…”

Section: Three-component Petasis Reactionsmentioning

confidence: 99%

Reactivity and Synthetic Applications of Multicomponent Petasis Reactions

2019

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“…Thus, recently Yuan and co‐workers showed how this reaction could be highly enhanced by sonication. Higher yields were not connected to all the tested substrates, but this method represents a valid alternative to the previously reported ones, that need longer reaction times with the same poor yields yet in the presence of catalysts such as TFA, La(OTf) 3 , molecular sieves or other energy sources, like MW (Scheme ) …”

Section: Multi‐component Reactions (Mcrs)mentioning

confidence: 87%

Ultrasound‐Assisted Multicomponent Reactions, Organometallic and Organochalcogen Chemistry

et al. 2018

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In the last two decades, the search for sustainability in chemical reactions has attached a lot of attention. In this focus review, the use of ultrasound (US) as an alternative energy source in organic synthesis is presented. The improvement of the performance of chemical reactions due to the cavitation effect has been previously studied and described. The use of US guarantees often higher yields than other green methodologies, as microwave or ball milling. The impressive positive effect of US in organic synthesis are demonstrated in this review mainly in organometallic and multi-component reactions (MCRs), aimed to prepare bioactive compounds. A particular attention is dedicated to the US-assisted synthesis of valuable organochalcogen compounds with pharmacological activity.[a] F.

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“…Characterizing the distribution of S in the host materials is essential to evaluate the homogeneity of S/host composites owing to its effect on the performance of Li–S batteries. [ 56 ] Designing appropriate composites coupling host materials with uniformly distributed S and detecting their hybrid patterns under microscopically are important. [ 57 ] However, S is inclined to sublimate under the high vacuum conditions of an electron microscope sample chamber, resulting in the loss of S from the composite cathode or the redistribution of S within a composite cathode.…”

Section: Component Analysis By Cryo‐stem With X‐ray Energy Dispersivementioning

confidence: 99%

Analyzing Energy Materials by Cryogenic Electron Microscopy

Ren

Zhang

et al. 2020

Advanced Materials

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Safe and high‐energy‐density rechargeable batteries are increasingly indispensable in the pursuit of a wireless and fossil‐free society. Advancements in present battery technologies and the investigation of next‐generation batteries highly depend on the ever‐deepening fundamental understanding and the rational designs of working electrodes, electrolytes, and interfaces. However, accurately analyzing energy materials and interfaces is severely hindered by their intrinsic limitations of air and electron‐beam sensitivity, which restrains the research of energy materials in a low‐efficiency trial‐and‐error paradigm. The emergence of cryogenic electron microscopy (cryo‐EM) has enabled the nondestructive characterization of air‐ and electron‐beam sensitive energy materials in the microscale and nanoscale, and even at atomic resolutions, affording closer insights into the primary chemistry and physics of working batteries. Herein, the development of cryo‐EM and the applications in detecting energy materials are reviewed and analyzed from its overwhelming advantages in disclosing the underlying mystery of energy materials. Critical sample preparation methods as the precondition for cryo‐EM are compared, which strongly affect the characterization accuracy. Furthermore, new developments in the analysis of energy materials, especially bulk electrodes and interfaces in lithium metal batteries, are presented according to different functions of cryo‐EM. Finally, future directions of cryo‐EM for analyzing energy materials are prospected.

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Petasis three-component reaction accelerated by trifluoroacetic acid: synthesis of indoline-derived glycines

Cited by 14 publications

References 18 publications

Reactivity and Synthetic Applications of Multicomponent Petasis Reactions

Reactivity and Synthetic Applications of Multicomponent Petasis Reactions

Ultrasound‐Assisted Multicomponent Reactions, Organometallic and Organochalcogen Chemistry

Analyzing Energy Materials by Cryogenic Electron Microscopy

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