ChemInform Abstract: Mild and Catalyst‐Free Petasis/Decarboxylative Domino Reaction: Chemoselective Synthesis of N‐Benzyl Propargylamines.

Feng, Huangdi; Jia, Huihui; Sun, Zhihua

doi:10.1002/chin.201518063

Cited by 2 publications

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“…In this manner, several propargylamines were synthesized chemoselectively in high yields. 247 A similar approach was also described later by Wang et al 248,249 Finally, Jiang et al reported the one-pot synthesis of N-aryl propargylamines through the reaction of aromatic boronic acid with aqueous ammonia and propargyl bromide under microwave-assisted conditions. The copper catalyst Cu 2 O was also used to promote the coupling of aromatic boronic acids with aqueous ammonia and the following propargylation by propargyl bromide.…”

Section: Synthesis Of Propargylamines Using Boronic Acids and Alkylbo...mentioning

confidence: 84%

Synthesis and Reactivity of Propargylamines in Organic Chemistry

et al. 2017

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Propargylamines are a versatile class of compounds which find broad application in many fields of chemistry. This review aims to describe the different strategies developed so far for the synthesis of propargylamines and their derivatives as well as to highlight their reactivity and use as building blocks in the synthesis of chemically relevant organic compounds. In the first part of the review, the different synthetic approaches to synthesize propargylamines, such as A couplings and C-H functionalization of alkynes, have been described and organized on the basis of the catalysts employed in the syntheses. Both racemic and enantioselective approaches have been reported. In the second part, an overview of the transformations of propargylamines into heterocyclic compounds such as pyrroles, pyridines, thiazoles, and oxazoles, as well as other relevant organic derivatives, is presented.

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Section: Synthesis Of Propargylamines Using Boronic Acids and Alkylbo...mentioning

confidence: 84%

Synthesis and Reactivity of Propargylamines in Organic Chemistry

et al. 2017

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“…This type of metal-free four-component PR was independently reported by two groups for the synthesis of N-benzyl propargylamines 108−111. 130,131 It is noteworthy that two components of formaldehyde are involved in this transformation to form the initial benzyl hemiaminal intermediate 107, and thus it can also be classified as a fivecomponent reaction (Scheme 34). Substituted propargylamines are versatile substrates for the synthesis of diverse heterocycles via a variety of synthetic transformations, such as RCM, ROM, and enyne cyclization reactions.…”

Section: Noncanonical Building Block As the Fourth Componentmentioning

confidence: 99%

Reactivity and Synthetic Applications of Multicomponent Petasis Reactions

2019

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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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ChemInform Abstract: Mild and Catalyst‐Free Petasis/Decarboxylative Domino Reaction: Chemoselective Synthesis of N‐Benzyl Propargylamines.

Cited by 2 publications

References 1 publication

Synthesis and Reactivity of Propargylamines in Organic Chemistry

Synthesis and Reactivity of Propargylamines in Organic Chemistry

Reactivity and Synthetic Applications of Multicomponent Petasis Reactions

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