Silver-catalysed [3 + 2] annulation reaction of aryldiazonium salts with allenes enabled by boronate direction

Peng, Xing; Zheng, Mengmeng; Pei, Qing; Xue, Xiao‐Song; Zhang, Fa‐Guang; Ma, Jun‐An

doi:10.1039/d2qo01585d

Cited by 2 publications

(1 citation statement)

References 87 publications

(19 reference statements)

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“…This protocol eliminated the need for pre-functionalization, toxic noble metal catalysts, harmful oxidants or other additives. A recent protocol applied a silver-catalyzed [3 + 2] cycloaddition of aryl diazonium salts and allenes, providing the target pyrazoles in moderate to excellent yields, however, in high selectivity [ 47 ]. A similar approach, using aryl diazonium salts with arylcyclopropanols produced the target pyrazoles by a photocatalytic cycloaddition [ 48 ].…”

Section: Five-membered Ringsmentioning

confidence: 99%

Green Synthesis of Aromatic Nitrogen-Containing Heterocycles by Catalytic and Non-Traditional Activation Methods

2023

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Recent advances in the environmentally benign synthesis of aromatic N-heterocycles are reviewed, focusing primarily on the application of catalytic methods and non-traditional activation. This account features two main parts: the preparation of single ring N-heterocycles, and their condensed analogs. Both groups include compounds with one, two and more N-atoms. Due to the large number of protocols, this account focuses on providing representative examples to feature the available methods.

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Section: Five-membered Ringsmentioning

confidence: 99%

Green Synthesis of Aromatic Nitrogen-Containing Heterocycles by Catalytic and Non-Traditional Activation Methods

2023

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Stereoselective Synthesis of 4‐Hydroxy‐1‐Silyl‐1‐Allenylboranes and Access to 2‐Silylethynyl‐1,3‐Diols

El Haj Brahim,

Ishak Dridi,

Abderrahim

et al. 2024

Asian J Org Chem

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The highly stereoselective gem‐silylboration of chiral 2‐substituted 1‐ethynylepoxides is reported herein. The reaction involves first the deprotonation of the epoxides in the acetylenic position followed by transmetallation with Et3SiBpin. The transient silylborane ate‐complexes generated undergo the stereoselective 1,2‐migration of the Et3Si‐group to the sp‐hybridized terminus carbon of the ethynyl‐moiety in a stereospecific anti‐addition. The moisture‐sensitive and thermally unstable 4‐hydroxy‐1‐triethylsilyl‐1‐allenyl(pinacolato)boranes thus obtained react with aldehydes through an SE2’‐mode of addition, affording highly functionalized 2‐triethysilylethynyl‐1,3‐diols with a good diastereoselectivity which is rationalized by a Yamamoto‐Houk type transition state model.

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Silver-catalysed [3 + 2] annulation reaction of aryldiazonium salts with allenes enabled by boronate direction

Abstract: Allenes are an unique type of powerful synthons for the construction of various carbocycles and heterocycles, but their annulation reactions with N-N triple bond electrophiles has not been disclosed. Here...

Cited by 2 publications

References 87 publications

Green Synthesis of Aromatic Nitrogen-Containing Heterocycles by Catalytic and Non-Traditional Activation Methods

Green Synthesis of Aromatic Nitrogen-Containing Heterocycles by Catalytic and Non-Traditional Activation Methods

Stereoselective Synthesis of 4‐Hydroxy‐1‐Silyl‐1‐Allenylboranes and Access to 2‐Silylethynyl‐1,3‐Diols

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