Iridium-catalyzed intramolecular [4 + 2] cycloadditions of alkynyl halides

Tigchelaar, Andrew; Tam, William

doi:10.3762/bjoc.8.201

Cited by 4 publications

(2 citation statements)

References 47 publications

(53 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Tigchelaar et al . disclose an investigation into the intramolecular [4+2] cycloadditions of diene‐tethered alkynyl halides 43 catalyzed by iridium, specifically with the use of [IrCl(cod)] 2 or IrCl(CO)(PPh 3 ) 2 as the catalyst and PPh 3 or BINAP as the ligand (Scheme , Table ).…”

Section: Synthetic Routes To Phthalansmentioning

confidence: 99%

Recent Advances in Phthalan and Coumaran Chemistry

et al. 2018

View full text Add to dashboard Cite

Oxygen‐containing heterocycles are common in biologically active compounds. In particular, phthalan and coumaran cores are found in pharmaceuticals, organic electronics, and other useful medical and technological applications. Recent research has expanded the methods available for their synthesis. This Minireview presents recent advances in the chemistry of phthalans and coumarans, with the goal of overcoming synthetic challenges and facilitating the applications of phthalans and coumarans.

show abstract

Section: Synthetic Routes To Phthalansmentioning

confidence: 99%

Recent Advances in Phthalan and Coumaran Chemistry

et al. 2018

View full text Add to dashboard Cite

show abstract

“…Considering the rich history of the concerted Diels–Alder cycloaddition, and modern advances in transition-metal catalysis of alternative reaction pathways, − strategic gaps in [4 + 2] annulation technology can be viewed as fundamentally problematic. Electron-deficient dienes, for example (unless stabilized by aromaticity), are limited by an underappreciated tendency to react with electron-deficient dienophiles, which often results in dimerization and/or oligomerization.…”

mentioning

confidence: 99%

Reaction Discovery Using Neopentylene-Tethered Coupling Partners: Cycloisomerization/Oxidation of Electron-Deficient Dienynes

2017

View full text Add to dashboard Cite

A rhodium-catalyzed cycloisomerization and oxidation of tethered dienynes for the synthesis of indanes is described. An auxiliary fragmentation/olefination method (also described herein) provides novel access to tethered alkyne-dienoate substrates. The reported method circumvents current limitations in and expands the scope of inverse-demand Diels-Alder-type cycloadditions. Traditional discovery substrates involving malonate-, ether-, and sulfonamide-based tethers are problematic in the current methodology, underscoring the unique virtue of neopentylene-tethered substrates for reaction discovery.

show abstract

Transition Metal-Catalyzed Reactions of Alkynyl Halides

Petko

Koh

Tam

2019

COS

View full text Add to dashboard Cite

Background: Transition metal-catalyzed reactions of alkynyl halides are a versatile means of synthesizing a wide array of products. Their use is of particular interest in cycloaddition reactions and in constructing new carbon-carbon and carbon-heteroatom bonds. Transition metal-catalyzed reactions of alkynyl halides have successfully been used in [4+2], [2+2], [2+2+2] and [3+2] cycloaddition reactions. Many carbon-carbon coupling reactions take advantage of metal-catalyzed reactions of alkynyl halides, including Cadiot-Chodkiewicz, Suzuki-Miyaura, Stille, Kumada-Corriu and Inverse Sonogashira reactions. All the methods of constructing carbon-nitrogen, carbon-oxygen, carbon-phosphorus, carbon-sulfur, carbon-silicon, carbon-selenium and carbon-tellurium bonds employed alkynyl halides. Objective: The purpose of this review is to highlight and summarize research conducted in transition metalcatalyzed reactions of alkynyl halides in recent years. The focus will be placed on cycloaddition and coupling reactions, and their scope and applicability to the synthesis of biologically important and industrially relevant compounds will be discussed. Conclusion: It can be seen from the review that the work done on this topic has employed the use of many different transition metal catalysts to perform various cycloadditions, cyclizations, and couplings using alkynyl halides. The reactions involving alkynyl halides were efficient in generating both carbon-carbon and carbonheteroatom bonds. Proposed mechanisms were included to support the understanding of such reactions. Many of these reactions face retention of the halide moiety, allowing additional functionalization of the products, with some new products being inaccessible using their standard alkyne counterparts.

show abstract

Iridium-catalyzed intramolecular [4 + 2] cycloadditions of alkynyl halides

Cited by 4 publications

References 47 publications

Recent Advances in Phthalan and Coumaran Chemistry

Recent Advances in Phthalan and Coumaran Chemistry

Reaction Discovery Using Neopentylene-Tethered Coupling Partners: Cycloisomerization/Oxidation of Electron-Deficient Dienynes

Transition Metal-Catalyzed Reactions of Alkynyl Halides

Contact Info

Product

Resources

About