Rhenium‐ and Manganese‐Catalyzed Insertion of Alkynes into a Carbon–Carbon Single Bond of Cyclic and Acyclic 1,3‐Dicarbonyl Compounds

Kuninobu, Yoichiro; Kawata, Atsushi; Nishi, Masatoshi; S, Salprima Yudha; Chen, Jingjin; Takai, Kazuhiko

doi:10.1002/asia.200900137

Cited by 44 publications

(20 citation statements)

References 31 publications

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“…This is followed by C-C bond formation at the α-carbon of the dicarbonyl and the cis-coordinated alkyne, to give a vinyl manganese species 322. [84] At this point the manganesediene undergoes nucleophilic addition to the carbonyl.…”

Section: Cyclisation Reactionsmentioning

confidence: 99%

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Recent Advances of Manganese Catalysis for Organic Synthesis

2016

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Manganese is a non‐toxic, inexpensive and earth abundant metal, so is a perfect candidate for catalysis whether as a replacement for precious metals or in the search for novel reactivity. Despite this, manganese catalysis has not undergone the same development of other earth‐abundant metals (particularly iron and cobalt). This review details recent synthetic methodologies using manganese catalysts, including C–H activation, late stage fluorination, hydrosilylation and cross‐coupling.

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Section: Cyclisation Reactionsmentioning

confidence: 99%

“…[83] Cyclooctanones could be prepared by inserting an alkyne into the carbon-carbon bond of a 1,3-dicarbonyl compound. [84]…”

Section: Cyclisation Reactionsmentioning

confidence: 99%

Recent Advances of Manganese Catalysis for Organic Synthesis

2016

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“…A similar reaction also proceeded using a manganese catalyst. 43 Compared with the rhenium catalyst, the manganese system requires higher reaction temperature (80°C) and has a narrow scope of alkynes.…”

Section: 41mentioning

confidence: 99%

“…43,45 The insertion of alkynes into a carboncarbon single bond also proceeded using acyclic ¢-keto esters. As a result, carbon chain extension products were formed as a mixture of olefinic regio-and stereoisomers.…”

Section: 41mentioning

confidence: 99%

Development of Novel and Highly Efficient Methods to Construct Carbon–Carbon Bonds Using Group 7 Transition-Metal Catalysts

Kuninobu

Takai

2012

Bulletin of the Chemical Society of Japan

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Rhenium-or manganese-catalyzed transformations based on the cleavage of inactive bonds, such as carbon hydrogen and carboncarbon bonds are discussed. Such transformations are recognized as key methods to realize efficient and powerful reactions. We also reveal novel regio-and/or stereodefined cycloaddition reactions using a rhenium or manganese catalyst. Most of the catalytic activities are typical of rhenium and manganese carbonyl complexes.

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“…Treatment of 98 with arylacetylenes bearing substituents such as electron‐donating methoxy and methyl groups and electron‐withdrawing trifluoromethyl and bromo groups afforded the corresponding eight‐membered cyclic compounds in 86–97 % yields. In 2009, they found that the reaction system can be promoted by the addition of 4 Å molecular sieves instead of a catalytic amount of phenylacetonitrile 45b…”

Section: [6+2] Cycloadditionsmentioning

confidence: 99%

Transition‐Metal‐Catalyzed Cycloadditions for the Synthesis of Eight‐Membered Carbocycles

Wang

2010

Chemistry An Asian Journal

166

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Eight-membered carbocycles are found in a wide variety of natural products that exhibit a broad range of biological and medicinal activities (cf. the most potent anticancer drug, taxol). However, the synthesis of eight-membered carbocycles is quite challenging as traditional approaches are met with entropic and enthalpic penalties in the ring-forming transition states. These negative effects can be totally or partially avoided with the implementation of transition-metal-catalyzed/mediated cycloadditions. In this Focus Review, examples of elegant and efficient metal-catalyzed and some metal-mediated cycloadditions (including Ni- catalyzed [4+4] and Rh-catalyzed [4+2+2] and [5+2+1] reactions) are presented to illustrate this. Application of these cycloaddition reactions in total synthesis is also presented to show the significance of these reactions in addressing challenges in natural product synthesis.

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Rhenium‐ and Manganese‐Catalyzed Insertion of Alkynes into a Carbon–Carbon Single Bond of Cyclic and Acyclic 1,3‐Dicarbonyl Compounds

Cited by 44 publications

References 31 publications

Recent Advances of Manganese Catalysis for Organic Synthesis

Recent Advances of Manganese Catalysis for Organic Synthesis

Development of Novel and Highly Efficient Methods to Construct Carbon–Carbon Bonds Using Group 7 Transition-Metal Catalysts

Transition‐Metal‐Catalyzed Cycloadditions for the Synthesis of Eight‐Membered Carbocycles

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