Catalyzed Domino Reaction Research Articles

Controllable stereoselective synthesis of pyrano[3,2-c]quinolines by lanthanide halides catalyzed aza-Diels-Alder reactions

An efficient method for the synthesis of tetrahydroquinoline derivatives via lanthanide halides catalyzed domino reactions of arylamines with dihydropyran is described. Either the cis or the trans isomer can be obtained as the major product in good yield by changing the catalyst and reaction conditions.

ChemInform Abstract: Gold(I)‐Catalyzed Cascade for Synthesis of Pyrrolo[1,2‐a:2′,1′‐c]‐/Pyrido[2,1‐c]pyrrolo[1,2‐a]quinoxalinones.

An efficient and convenient method was developed for the one-pot construction of the complex polycyclic heterocycles pyrrolo[1,2-a:2',1'-c]-/ pyrido[2,1-c]pyrrolo[1,2-a]quinoxalinones from two simple starting materials via a gold(I)-catalyzed domino reaction. This strategy presents an atom economical and environmentally friendly transformation, in which two new C-N bonds and one new C-C bond are formed in a one-pot reaction process.

ChemInform Abstract: Gold‐Catalyzed Domino Reactions Consisting of Regio‐ and Stereoselective 1,2‐Alkyl Migration.

AbstractA cationic gold(I)‐catalyzed domino reaction involving highly regio‐ and stereoselective 1,2‐alkyl migration and heterocyclization or oxygen transfer is developed, in which the product selectivity is controlled by the counteranion of the gold catalyst.

A facile method for synthesis of polysubstituted naphthalene derivatives through pyrrolidine catalyzed domino reaction

A novel synthetic method for polysubstituted naphthalene derivatives via a pyrrolidine-mediated cascade Michael/Henry reaction was developed, in which easily prepared 2-(2-oxoethyl)benzaldehydes and nitroalkenes were employed as the starting materials. The reaction consists of four consecutive reactions that include a cascade Michael/Henry reaction, a dehydration reaction, and an aromatization reaction in one pot to afford synthetically important naphthalene derivatives with moderate yields.

Gold(I)‐Catalyzed Cascade for Synthesis of Pyrrolo[1,2‐a:2′,1′‐c]‐/Pyrido[2,1‐c]pyrrolo[1,2‐a]quinoxalinones

AbstractAn efficient and convenient method was developed for the one‐pot construction of the complex polycyclic heterocycles pyrrolo[1,2‐a:2′,1′‐c]‐/pyrido[2,1‐c]pyrrolo[1,2‐a]quinoxalinones from two simple starting materials via a gold(I)‐catalyzed domino reaction. This strategy presents an atom economical and environmentally friendly transformation, in which two new CN bonds and one new CC bond are formed in a one‐pot reaction process.

Gold‐Catalyzed Domino Reactions Consisting of Regio‐ and Stereoselective 1,2‐Alkyl Migration

A cationic gold(I)-catalyzed domino reaction involving highly regio- and stereoselective 1,2-alkyl migration and heterocyclization or oxygen transfer is developed, in which the product selectivity is controlled by the counteranion of the gold catalyst.

PdCl2‐Catalyzed Domino Reactions of 2‐Alkynylbenzaldehydes with Indoles: Synthesis of Fluorescent 5H‐Benzo[b]carbazol‐6‐yl Ketones

Synthetic methods: A new, selective Pd-catalyzed domino reaction of 2-alkynylbenzaldehydes with indoles has been developed for the synthesis of 5H-benzo[b]carbazol-6-yl ketones. The isobenzopyrylium complex is trapped by indole at room temperature to give 3-(1H-isochromen-1-yl)-1H-indoles, which can be transformed into 5H-benzo[b]carbazol-6-yl ketones by raising the temperature (see scheme). These ketones exhibit intense fluorescence and interact with metal ions to enhance the fluorescence intensity.

A Chemistry Cascade: From Physical Organic Studies of Alkoxy Radicals to Alkaloid Synthesis

In this Perspective, I present a personal account of a succession of chemical projects that I was involved with, each of which triggered or initiated my next research undertaking. It started with my early work in the field of physical organic photochemistry, which, in turn, guided me to my current research dealing with the synthesis of biologically active alkaloids. The article highlights some of the dominant themes of my research program over the past 48 years. Subject matter that is discussed includes the generation of reactive intermediates by photoexcitation, [1,3]-dipolar cycloaddition chemistry, rhodium(II)-catalyzed domino reactions of alpha-diazo carbonyl compounds, intramolecular [4 + 2]-cycloaddition of 2-amidofurans, and the utilization of various thio fragments for the synthesis of nitrogen heterocycles.

ChemInform Abstract: Palladium(II)-Catalyzed Domino Reaction of 2-(1-Alkynyl)-2-alken-1-ones with Nucleophiles: Scope, Mechanism and Synthetic Application in the Synthesis of 3,4-Fused Bicyclic Tetrasubstituted Furans.

Described herein is the development of a palladium(II)-catalyzed two- or three-component reaction of 2-(1-alkynyl)-2-alken-1-ones with nucleophiles and allylic chlorides. Various types of nucleophiles such as O-, N-, C-based nucleophiles and olefin-tethered O-, N-, C-based nucleophiles were investigated. The scope, mechanism and application of this Pd(II)-catalyzed domino reaction were studied. In these transformations, the palladium catalyst exhibits a dual role, serving simultaneously as a Lewis acid and a transition metal. Two possible reaction pathways (cross-coupling reaction vs. Heck reaction) from the same intermediate furanylpalladium species were observed. The reaction pathway is dependent on the property of the nucleophile and the length of the tethered chain as well. When olefin-tethered O-based nucleophiles were used, only the cross-coupling reaction pathway was observed, in contrast, both reaction pathways were observed when olefin-tethered C-based nucleophiles were employed. The product ratio is dependent on the length of the tethered chain. Furthermore, ring-closing metathesis (RCM) of corresponding furans with C=C bonds provides an easy method for the preparation of functionalized oxygen-heterocycles - 3,4-fused bicyclic furans. It is also noteworthy that allylic chloride can be as an oxidant besides its well known function as an alkylating reagent.

ChemInform Abstract: PPh3‐Catalyzed Domino Reaction: A Facile Method for the Synthesis of Chroman Derivatives.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Palladium(II)‐Catalyzed Domino Reaction of 2‐(1‐Alkynyl)‐2‐alken‐1‐ones with Nucleophiles: Scope, Mechanism and Synthetic Application in the Synthesis of 3,4‐Fused Bicyclic Tetrasubstituted Furans

Abstractmagnified imageDescribed herein is the development of a palladium(II)‐catalyzed two‐ or three‐component reaction of 2‐(1‐alkynyl)‐2‐alken‐1‐ones with nucleophiles and allylic chlorides. Various types of nucleophiles such as O‐, N‐, C‐based nucleophiles and olefin‐tethered O‐, N‐, C‐based nucleophiles were investigated. The scope, mechanism and application of this Pd(II)‐catalyzed domino reaction were studied. In these transformations, the palladium catalyst exhibits a dual role, serving simultaneously as a Lewis acid and a transition metal. Two possible reaction pathways (cross‐coupling reaction vs. Heck reaction) from the same intermediate furanylpalladium species were observed. The reaction pathway is dependent on the property of the nucleophile and the length of the tethered chain as well. When olefin‐tethered O‐based nucleophiles were used, only the cross‐coupling reaction pathway was observed, in contrast, both reaction pathways were observed when olefin‐tethered C‐based nucleophiles were employed. The product ratio is dependent on the length of the tethered chain. Furthermore, ring‐closing metathesis (RCM) of corresponding furans with CC bonds provides an easy method for the preparation of functionalized oxygen‐heterocycles – 3,4‐fused bicyclic furans. It is also noteworthy that allylic chloride can be as an oxidant besides its well known function as an alkylating reagent.

PPh3-Catalyzed Domino Reaction: A Facile Method for the Synthesis of Chroman Derivatives

A novel domino reaction catalyzed by triphenylphosphine was developed for synthesis of the highly functionalized chroman derivatives. The first example that the gamma-CH(3) of allenoate undergoes cyclization to form chroman derivates was reported.

Synthesis of Annulated 1,4-Dioxanes and Perhydro-1,4-oxazines by Domino-Wacker-Carbonylation and Domino-Wacker-Mizoroki-Heck Reactions

Palladium(II)-catalyzed domino reactions for the formation of 1,4-dioxanes and perhydro-1,4-oxazines starting from hydroxy alkenes are described. The domino-Wacker-carbonylation comprises a Wacker oxidation, subsequent CO-insertion and a nucleophilic substitution of the intermediately formed Pd-species. The domino-Wacker-Mizoroki-Heck reaction proceeds via a Wacker oxidation, subsequent insertion into the olefinic π-bond of α,β-unsaturated carbonyl compounds and β-hydride elimination.

Domino reactions of rhodium(ii) carbenoids for alkaloid synthesis

In this tutorial review, the rhodium(II)-catalyzed domino reactions of alpha-diazo carbonyl compounds are summarized. The article will emphasize some of the more recent synthetic applications of the rhodium carbenoid cyclization/cycloaddition domino cascade for alkaloid synthesis. The many structurally diverse and highly successful examples of both oxa and azapolycyclic ring formation cited in this tutorial review clearly demonstrate that the domino cyclization/cycloaddition cascade of metallo carbenoids has evolved as an important strategy for the synthesis of nitrogen containing natural products.

Pd(OAc)2‐Catalyzed Domino Reactions of 1‐Chloro‐2‐haloarenes and 2‐Haloaryl Tosylates with Hindered Grignard Reagents via Palladium‐Associated Arynes.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

Highly Enantioselective Organocatalytic Michael-Aldol Domino Reactions

l-Proline derivative 1 catalyzed domino reactions of thiol 2 with α,β-unsaturated aldehydes 3 are reported. A Michael-aldol domino reaction takes place in the presence of benzoic acid as additive providing tetrahydrothiophene carbaldehydes 4 in good yields and with excellent enantio- and diastereoselectivities. Under basic conditions (NaHCO3), the Michael addition is followed by enolization of the Michael adduct, yielding (tetrahydrothiophen-2-yl)phenyl methanones 5 with moderate yields and enantioselectivities.

Pd(OAc)2-Catalyzed Domino Reactions of 1-Chloro-2-haloarenes and 2-Haloaryl Tosylates with Hindered Grignard Reagents via Palladium-Associated Arynes

The palladium-associated aryne generation strategy and Pd(OAc)(2)-catalyzed annulative Domino reactions of 1-chloro-2-halobenzenes and 2-haloaryl tosylates with hindered Grignard reagents via palladium-associated arynes are described. The palladium-associated aryne generation strategy described here not only allows the high yield, one-step access to potentially useful substituted fluorenes from readily available 1-chloro-2-halobenzenes and 2-haloaryl tosylates, but may also lead to the development of other tandem reactions based on these readily available ortho leaving group bearing haloarenes. [reaction: see text]

A Highly Efficient Synthesis of 1,2,3,4‐Tetrahydroquinolines by Molecular Iodine Catalyzed Domino Reaction of Anilines with Cyclic Enol Ethers.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

Gold(III)‐ and Platinum(II)‐Catalyzed Domino Reaction Consisting of Heterocyclization and 1,2‐Migration: Efficient Synthesis of Highly Substituted 3(2H)‐Furanones

PtCl2-catalyzed alkyne activation initiates a domino reaction, in which a heterocyclization is followed by a 1,2-alkyl migration, for the construction of a variety of substituted 3(2H)-furanones. This stereospecific reaction is proposed to proceed through an oxonium ion intermediate (see scheme).

A highly efficient synthesis of 1,2,3,4-tetrahydroquinolines by molecular iodine-catalyzed domino reaction of anilines with cyclic enol ethers

A highly efficient method for the synthesis of 1,2,3,4-tetrahydroquinoline derivatives via a molecular iodine catalyzed domino reaction of anilines with cyclic enol ethers, such as 2,3-dihydrofuran and 3,4-dihydro-2 H-pyran, is described. The reaction may proceed through an aza-Diels–Alder process between an in situ generated 2-azadiene and another equivalent of cyclic enol.