Rhodium-Catalyzed [(3+2)+1] Carbocyclization Reactions of Alkynylidenecyclopropanes with Carbon Monoxide: Regiospecific Construction of Polysubstituted Phenols

Evans, P. Andrew; Burnie, Andrew J.; Negru, Daniela E.

doi:10.1021/ol501724s

Cited by 28 publications

(7 citation statements)

References 43 publications

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“…Compared to the ring‐opening strategy,,,,–,, the nucleophilic‐addition strategy––,,–, appears to be superior and more practical owning to the easily accessible substrates and the resulting products being more functionalized . However, such events are limited to the use of the inherent nucleophilic groups, and challenges in the preparation of reaction partners have restricted this strategy.…”

Section: Methodsmentioning

confidence: 99%

Palladium‐Catalyzed Reductive [5+1] Cycloaddition of 3‐Acetoxy‐1,4‐enynes with CO: Access to Phenols Enabled by Hydrosilanes

Song

Luo

et al. 2018

Angew Chem Int Ed

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A new palladium-catalyzed reductive [5+1] cycloaddition of 3-acetoxy-1,4-enynes with CO, enabled by hydrosilanes, has been developed for delivering valuable functionalized phenols. This methodology employs hydrosilanes as the external reagent to facilitate the [5+1] carbonylative benzannulation. The reaction is a conceptually and mechanistically novel carbonylative cycloaddition route for the construction of substituted phenols, through the formation of four new chemical bonds, with excellent functional-group tolerance.

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Section: Methodsmentioning

confidence: 99%

Palladium‐Catalyzed Reductive [5+1] Cycloaddition of 3‐Acetoxy‐1,4‐enynes with CO: Access to Phenols Enabled by Hydrosilanes

Song

Luo

et al. 2018

Angew Chem Int Ed

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“…Cationic rhodium(I)/modified BINAP catalyzed chemo‐ and regioselective [2+2+2] cycloaddition of 1,6‐diynes with terminal or silylated alkynes gave highly functionalized isoindolines 153 (Scheme 114). [216] In addition, rhodium(I) N ‐heterocyclic carbene, [217] cationic rhodium(I) with N ‐phosphino tert ‐butylsulfinamides, [218] rhodium(I)/cationic 2,2’‐bipyridyl, [219] rhodium(I) and phosphoramidite capped phosphorus dendrimers, [220] rhodium‐phophine/carbon monoxide, [221] and rhodium‐phophine/CuBr [222] complexes were also highly effective to catalyze the [2+2+2] cycloaddition of 1,6‐diynes with alkynes leading to tetrasusbtituted isoindolines.…”

Section: Synthesis Of Isoindolinesmentioning

confidence: 99%

Recent Developments in the Cyclization of Alkynes and Nitrogen Compounds for the Synthesis of Indole Derivatives

Neto

Zeni

2021

Asian J Org Chem

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This review is intended to highlight the most useful approaches for the synthesis of indole derivatives (azaindoles, carbazoles, carbolines, indazoles, 3H-indoles, indolines, indolizines, isoindoles, and isoindolines), which were described by using transition-metal catalyzed cyclization reactions of alkynes and nitrogen compounds. The methodologies carried out under metal-free conditions will also be illustrated herein. This review will cover the data published mostly in the past decade. Synthesis of 6-AzaindolesAzaindoles, although rare in nature, have attracted a significant attention because some synthetic structures containing this nucleus exhibit biological activities. [17] The synthetic methods describing the preparation of azaindoles are limited. Usually their synthesis was achieved from the cyclization reaction of substrates containing aminopyridines. [18] Transition Metal-Free Synthesis of 6-AzaindolesWe have nominated two methodologies for the preparation of 6-azaindoles, which were developed using alkynes and nitrogen compounds in a metal-free protocol. In the first, an electrophilic cyclization condition, using iodine as an electrophilic source, was applied to 2-(azidomethyl)-3-alkynyl-pyrroles in the preparation of 4-iodo-6-azaindoles 1 (Scheme 1, eq 1). [19] The second approach described the preparation of 2,5-disubstituted 6azaindoles 2 from base-catalyzed intramolecular cyclization of 2-(azidomethyl)-3-alkynyl-pyrroles (Scheme 1, eq 2). [20] 3. Synthesis of 7-Azaindoles Transition Metal-Catalyzed Synthesis of 7-Azaindoles Silver-Catalyzed Synthesis of 7-AzaindolesSilver-catalyzed cyclization reactions of alkynes constitute powerful strategies for the construction of heterocycles. In particular, the 7-azaindoles could be obtained by these approaches. A general method for the preparation of aryl-[a] Dr. J.

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“…The Negru group describes the use of the same methodology for the carbonylative [3+2+1] cycloaddition of alkylidenecyclopropanes 34 to give bicyclic phenols 35 (Scheme ).…”

Section: Synthetic Routes To Phthalansmentioning

confidence: 99%

Recent Advances in Phthalan and Coumaran Chemistry

et al. 2018

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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.

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Rhodium-Catalyzed [(3+2)+1] Carbocyclization Reactions of Alkynylidenecyclopropanes with Carbon Monoxide: Regiospecific Construction of Polysubstituted Phenols

Cited by 28 publications

References 43 publications

Palladium‐Catalyzed Reductive [5+1] Cycloaddition of 3‐Acetoxy‐1,4‐enynes with CO: Access to Phenols Enabled by Hydrosilanes

Palladium‐Catalyzed Reductive [5+1] Cycloaddition of 3‐Acetoxy‐1,4‐enynes with CO: Access to Phenols Enabled by Hydrosilanes

Recent Developments in the Cyclization of Alkynes and Nitrogen Compounds for the Synthesis of Indole Derivatives

Recent Advances in Phthalan and Coumaran Chemistry

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