The first example of palladium-catalyzed intermolecular allylaryloxylation of an internal alkyne by allyl aryl ethers

Kuniyasu, Hitoshi; Takekawa, K.; Sanagawa, Atsushi; Wakasa, Takashi; Iwasaki, Takanori; Kambe, Nobuaki

doi:10.1016/j.tetlet.2011.08.065

Cited by 7 publications

(2 citation statements)

References 26 publications

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“…29,30 Through a related process, disubstituted alkynes 75 have been shown to react with allyl ethers 76 to afford the synaddition products 77 (Scheme 18). 31 The challenging intermolecular manifold was facilitated through the use of an electronically biased alkyne to control regioselectivity.…”

Section: Accessing Sigmatropic Rearrangementsmentioning

confidence: 99%

π-Acid Mediated Insertion of Alkynes into Carbon–Heteroatom σ-Bonds

Adcock

Davies

2012

Synthesis

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The rapidly expanding field of gold and platinum π-acid catalysis has led to the discovery of diverse transformations that are initiated with nucleophilic attack onto a metal-activated alkyne. This review brings together those reactions which employ a heteroatom nucleophile bearing a functional group that can subsequently migrate to effect a formal insertion of the alkyne into a carbonheteroatom σ-bond. This reactivity profile is encountered in a range of efficient and powerful cycloisomerisations for the preparation of carbo-and heterocycles.

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Section: Accessing Sigmatropic Rearrangementsmentioning

confidence: 99%

π-Acid Mediated Insertion of Alkynes into Carbon–Heteroatom σ-Bonds

Adcock

Davies

2012

Synthesis

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“…On the other hand, aryl allyl ethers are important precursors in organic synthesis and have been found to be widely used in natural product total synthesis and aromatic Claisen rearrangement . However, aryl allyl ethers are not commonly used in transition-metal-catalyzed domino reactions because of their high stabilities . Herein, we report a general method for both 2-substituted 2,3-dihydrobenzofurans and indolines synthesis from the functionalized aryl allyl ethers through an unexpected vinylogous elimination/intermolecular Heck coupling/intramolecular allylation domino reaction sequence (Scheme ).…”

Section: Introductionmentioning

confidence: 99%

Vinylogous Elimination/Heck Coupling/Allylation Domino Reactions: Access to 2-Substituted 2,3-Dihydrobenzofurans and Indolines

Yang

Jin

et al. 2018

J. Org. Chem.

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A highly regio- and stereoselctive palladium-catalyzed domino reaction of functionalized aryl allyl ethers has been developed. Various aryl allyl ethers derived from the phosphine-catalyzed addition of electron-deficient allenes with phenol are found to be efficient substrates for the synthesis of 2-substituted 2,3-dihydrobenzofurans and indolines. It is the first example of aryl allyl ether used as an ideal and practical precursor of hard to get functionalized 1,3-butadiene for the heterocyclic compound synthesis.

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Double Functionalization of Alkynes by Addition of Carbon–Element Bonds

2022

Addition Reactions With Unsaturated Hydrocarbons

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The first example of palladium-catalyzed intermolecular allylaryloxylation of an internal alkyne by allyl aryl ethers

Cited by 7 publications

References 26 publications

π-Acid Mediated Insertion of Alkynes into Carbon–Heteroatom σ-Bonds

π-Acid Mediated Insertion of Alkynes into Carbon–Heteroatom σ-Bonds

Vinylogous Elimination/Heck Coupling/Allylation Domino Reactions: Access to 2-Substituted 2,3-Dihydrobenzofurans and Indolines

Double Functionalization of Alkynes by Addition of Carbon–Element Bonds

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