Gold-Catalyzed Alkynylative Meyer–Schuster Rearrangement

Banerjee, Somsuvra; Ambegave, Shivhar B.; Mule, Ravindra D; Senthilkumar, Beeran; Patil, Nitin T.

doi:10.1021/acs.orglett.0c01596

Cited by 28 publications

(13 citation statements)

References 94 publications

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“…Very recently, a gold‐catalyzed alkynylative MSR has been reported (Scheme 9). [44] It involved reaction of propargylic alcohols with ethynylbenziodoxolones in the presence of gold catalysts. After optimization studies, the catalyst 28 k proved to give the best results and a wide range of target molecules 48 could be obtained in good to excellent yields.…”

Section: New Catalytic Systems Leading To αβ‐Unsaturated Carbonyl Dementioning

confidence: 99%

Recent Developments in the Meyer‐Schuster Rearrangement

Justaud¹,

Hachem

Grée³

2021

Eur J Org Chem

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Most of this review article has been prepared during Covid 19 pandemy. Therefore, we dedicate it,-first to all persons who unfortunately died from this disease and,-second to all people (medical doctors and many others) who helped their congeners to survive to this pandemy. The Meyer-Schuster rearrangement is an efficient method to prepare α,β-unsatured carbonyl compounds starting from propargylic alcohols and this review presents the remarkable progress made during the last decade in this reaction. New efficient catalytic systems have been discovered and many elegant applications have been reported for this rearrangement. To be noticed in particular are the new and efficient cascade processes affording a wide range of carbo-and heterocyclic molecules. Moreover, brilliant applications of this rearrangement have been described as well, in the total synthesis of complex natural products and their analogues. Finally, the first examples of aza-Meyer-Schuster rearrangements have been recently described as well.

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Section: New Catalytic Systems Leading To αβ‐Unsaturated Carbonyl Dementioning

confidence: 99%

Recent Developments in the Meyer‐Schuster Rearrangement

Justaud¹,

Hachem

Grée³

2021

Eur J Org Chem

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“…[229] Very recently, Patil et al disclosed the alkynylative Meyer-Schuster rearrangement by employing an interplay mode by combining two distinct reactivity patterns of gold catalysis such as π-activation and cross-coupling (Scheme 51, eq 2). [230] In this chemistry, Au(I)-precatalyst undergoes oxidative addition by TIPS-EBX 217 to form catalytically active alkynylAu(III)-, a key species which triggers a sequential Meyer-Schuster rearrangement/alkynylation of propargyl alco- -diol derivatives 220 which has not been explored until then. They exposed the Au(I)-catalyzed synthesis of several αhydroxy-α-vinylcyclopentanones 221 through an unprecedented Meyer Schuster/ring expansion cascade occurring through a hydrogen-bonding mechanism (Scheme 51, eq 3).…”

Section: Meyer-schuster Rearrangementmentioning

confidence: 99%

“…[229] Very recently, Patil et al disclosed the alkynylative Meyer-Schuster rearrangement by employing an interplay mode by combining two distinct reactivity patterns of gold catalysis such as π-activation and cross-coupling (Scheme 51, eq 2). [230] In this chemistry, Au(I)-precatalyst undergoes oxidative addition by TIPS-EBX 217 to form catalytically active alkynylAu(III)-, a key species which triggers a sequential Meyer-Schuster rearrangement/alkynylation of propargyl alco-Scheme 48. Gold vs vanadium in influencing the product divergence.…”

Section: Meyer-schuster Rearrangementmentioning

confidence: 99%

Regio‐ and Site‐selective Molecular Rearrangements by Homogeneous Gold Catalysis

Praveen

2020

Asian J Org Chem

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Homogeneous gold catalysis for connection and disconnection of carbon-carbon (CÀ C) as well as carbonheteroatom (CÀ X) bond constitutes an important zone in molecular chemistry, since all new or existing organic synthesis relies on the transformation of these chemical bonds. Among the diaspora of molecular transformations, rearrangement and shift reactions occupy a special place in organic chemistry, as they enable the synthesis of molecules of increased complexity from simple precursors. However, the rearrangement in substrates possessing more than one potential reaction site produce more than one isomer and could result in regioselective issues. This challenge of selective synthesis of one regisomer over the other was fairly addressed by gold catalysis on various occasions. To this end, the prowess of homogeneous gold catalysis towards regioselective molecular rearrangement reactions and the contributing parameters are comprehensively reviewed. Also, synthetic applicability of regioselective rearrangements by gold catalysis in total and formal synthesis of several natural products was emphasized.This review also covers the emergence of gold catalyzed migratory/shift selective reactions and could be beneficial for synthetic and medicinal chemists.

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“…Further, this intermediate undergoes carbophilic activation on coordinating with alkynol to form another intermediate which leads to Meyer‐Schuster rearrangement gives third intermediate. In final step, reductive elimination of third intermediate affords desired enynone and catalyst is regenerated [128] …”

Section: Transformations Involving Hypervalent Iodine Reagents and 3r...mentioning

confidence: 99%

“…In final step, reductive elimination of third intermediate affords desired enynone and catalyst is regenerated. [128] Scheme 121. Synthesis of cyclic conjugated dienes.…”

Section: Alkynylative Meyer-schuster Rearrangementmentioning

confidence: 99%

Combined Approach of Hypervalent Iodine Reagents and Transition Metals in Organic Reactions

et al. 2022

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This review outlines the progress over recent years in the reactions involving combined approach of hypervalent iodine reagents and transition metals such as palladium, nickel, iridium, gold, rhodium, copper, iron, ruthenium, platinum, silver, zinc, rhenium and cobalt. This approach enables organic transformations complimentary to traditional manifolds. Hypervalent iodine reagents play a preeminent role in organic chemistry due to their versatile reactivity, heteroatom ligands and mild reaction conditions. These reagents in combination of transition metal compounds are used in many synthetically useful organic reactions such as oxidation, rearrangement, amination, halogenation, amidation, ring-opening, cyclization and CÀ H and CÀ C functionalization reactions, etc. which are discussed here. Combination with Cobalt 2.3. Reactions of Hypervalent Iodine Reagents with Copper 2.4. Reactions of Hypervalent Iodine Reagents in Combination with Nickel 2.5. Reactions of Hypervalent Iodine Reagents in Combination with Zinc 3. Transformations Involving Hypervalent Iodine Reagents and 2 nd Transition Series Metals 3.1. Reactions of Hypervalent Iodine Reagents in Combination with Ruthenium 3.2. Reactions of Hypervalent Iodine Reagents in Combination With Rhodium 3.3. Reactions of Hypervalent Iodine Reagent in Combination With Palladium 3.4. Reactions of Hypervalent Iodine Reagents in Combination with Silver 4. Transformations Involving Hypervalent Iodine Reagents and 3rd Transition Series Metals 4.1. Reactions of Hypervalent Iodine Reagents in Combination with Rhenium 4.2. Reactions of Hypervalent Iodine Reagents in Combination with Iridium 4.3. Reactions of Hypervalent Iodine Reagents in Combination with Platinum 4.4. Reactions of Hypervalent Iodine Reagents in Combination with Gold 5. Conclusion

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Gold-Catalyzed Alkynylative Meyer–Schuster Rearrangement

Cited by 28 publications

References 94 publications

Recent Developments in the Meyer‐Schuster Rearrangement

Recent Developments in the Meyer‐Schuster Rearrangement

Regio‐ and Site‐selective Molecular Rearrangements by Homogeneous Gold Catalysis

Combined Approach of Hypervalent Iodine Reagents and Transition Metals in Organic Reactions

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