Nickel-Catalyzed Favorskii-Type Rearrangement of Cyclobutanone Oxime Esters to Cyclopropanecarbonitriles

Shuai, Bin; Fang, Ping; Mei, Tian‐Sheng

doi:10.1055/s-0039-1690872

Cited by 6 publications

(3 citation statements)

References 5 publications

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“…Yorimitsu describes the development of a general Negishi-type cross-coupling reaction of easily accessible trialkylsulfonium salts, 7 while Fleischer and Berkefeld report the utilization of a Ni catalyst to cleave simple allyl ethers chemoselectivity via formal sp 3 C-O functionalization. 8 The groups of Mei and Fang 9 and Wang 10 demonstrate that Favorskii rearrangements and reductive allylic defluorinative coupling reactions are not only within reach, but also allow rapid access to cyclopropanes decorated with nitriles or aliphatic alcohols possessing a difluoroalkene isostere on the alkyl side chain. Ogoshi 11 and Kimura, 12 respectively, describe the development of carbonylation and carboxylation methods for rapidly and reliably accessing -lactams and carboxylic acids possessing alkenes on the side chain.…”

Section: Cluster Synlettmentioning

confidence: 99%

Cluster Preface: Modern Nickel-Catalyzed Reactions

Martı́n

Molander

2021

Synlett

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Ruben Martin is a professor at the Institute of Chemical Research of Catalonia (ICIQ), Tarragona, Spain. He received his Ph.D. in 2003 from the University of Barcelona under the guidance of Prof. Antoni Riera. In 2004, he moved to the Max-Planck Institut für Kohlenforschung as a Humboldt postdoctoral fellow with Prof. Alois Fürstner. In 2005, he undertook further postdoctoral studies at MIT with Prof. Stephen L. Buchwald as a MEC-Fulbright fellow. In 2008, he began his independent career as an assistant professor at the ICIQ (Tarragona). In 2013, he was promoted to associate professor and shortly after to ICREA Research Professor. Ruben Martin has focused his career on designing synthetically useful Ni-catalyzed methodologies for streamlining the preparation of added-value chemicals from simple precursors without losing sight of mechanistic considerations, when appropriate. Gary A. Molander is a professor at the University of Pennsylvania, Philadelphia, United States. He completed his undergraduate studies in chemistry at Iowa State University under the tutelage of Prof. Richard C. Larock. He earned his Ph.D. at Purdue University under the direction of Prof. Herbert Brown and undertook postdoctoral training with Prof. Barry Trost at the University of Wisconsin, Madison. He began his academic career at the University of Colorado, Boulder, moving to the University of Pennsylvania in 1999, where he is currently Professor of Chemistry. His research interests have focused on the utilization of organolanthanides, Pd-catalyzed cross-coupling reactions with trifluoroborate salts, and the merger of photoredox catalysis and Ni catalysis for tackling a priori uphill transformations under visible-light irradiation for accessing valuable scaffolds in both academic and pharmaceutical laboratories.

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Section: Cluster Synlettmentioning

confidence: 99%

Cluster Preface: Modern Nickel-Catalyzed Reactions

Martı́n

Molander

2021

Synlett

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“…Common approaches are reactions of olefines with cyanomethyl carbenoids, prepared from the catalyzed decomposition of diazo compounds, [6] cyanomethyl radical additions, [7] Corey À Chaykovsky reactions, [8] reactions of alkenes with hypervalent iodine reagents, [9] Michael-Induced Ring Closure (MIRC) reactions carried out with doubly activated methylene compounds and electron-poor alkenes, [10] or rearrangement reactions. [11] Each of these methods present interesting advantages together with peculiar drawbacks such as hazardous/unstable reagents, expensive catalysts, poor yields, narrow scope or low stereoselectivity. The development of complementary strategies that use easy to handle reaction partners and ensure structural diversification of the cyclopropyl unit continues to be highly desirable.…”

Section: Introductionmentioning

confidence: 99%

Cyclopropanation of Aryl and Styryl Acetonitriles With Selenium‐Based Dielectrophiles

Coelho Dias,

Allegrini,

Wielgus

et al. 2024

Eur J Org Chem

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Efficient cyclopropanation reactions of aryl or styrylacetonitriles with vinyl selenones under mild conditions were described. By this approach, synthetically challenging 1‐vinylcyclopropane‐1‐carbonitriles were accessible in good yields. This methodology features the advantage of operational simplicity, broad substrate scope, good functional group tolerance, transition‐metal‐free conditions, mild temperature, and a high level of regio‐ and diastereo‐control.

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“…In addition to the cyclopropanation of alkenes, the synthesis of cyclopropanes could also be accessed through the ring-contraction reaction of cyclobutane derivatives. For example, α-substituted cyclobutanones 11 and cyclobutanone oxime esters 12 undergo a (quasi-)Favorskii rearrangement reaction easily under alkaline conditions, resulting in the formation of cyclopropyl ketones and nitriles, respectively. As with the 3-(2-bromophenyl)cyclobutanone, it could undergo the ring-contraction reaction through a palladium-catalyzed sequential ring-opening/cross-coupling reaction.…”

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confidence: 99%