Pd-Catalyzed α-Arylation of Sulfones in a Three-Component Synthesis of 3-[2-(Phenyl/methylsulfonyl)ethyl]indoles

Solé, Daniel; Pérez‐Janer, Ferran; Zulaica, Ester; Guastavino, Javier Fernando; Fernández, Israel

doi:10.1021/acscatal.6b00027

Cited by 18 publications

(21 citation statements)

References 87 publications

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“…The intramolecular Heck coupling furnishes, after The reaction of substituted 2-iodoanilines 13 and vinyl sulfones 14 produced a particular four step domino process with the formation of 3-substituted indoles 15 in good yields (Scheme 5). 8 The sequence is based on an initial intermolecular aza-Michael reaction followed by intramolecular Pd-catalyzed -arylation of the sulfone. This intermediate undergoes a Michael addition with a second molecule of vinyl sulfone and -elimination of sulfinic acid forms the products 15.…”

Section: Scheme 3 2-chlorophenyl Triflates As Versatile Substrates Tomentioning

confidence: 99%

Pd-Catalyzed Domino Reactions Involving Alkenes To Access Substituted Indole Derivatives

et al. 2020

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Palladium-catalyzed domino reactions are advanced tools in achieving various nitrogen-containing heterocycles in an efficient and economical manner due to the reduced number of steps in the process. This review highlights recent advances in domino processes aimed at the synthesis of indole derivatives and polycyclic systems containing the indole nucleus in intra/intra- or intra/intermolecular reactions. In particular, we consider domino processes that involve a double bond in a step of the sequence, which allow the issue of regioselectivity in the cyclization to be faced and overcome. The different sections in this review focus on the synthesis of the indole nucleus and functionalization of the scaffold starting from different substrates that have been identified as activated starting materials, which involve a halogenated moiety or unactivated unsaturated systems. In the former case, the reaction is under Pd(0) catalysis, and in the second case a Pd(II) catalytic species is required and then an oxidant is necessary to reconvert the Pd(0) into the active Pd(II) species. On the other hand, the second method has the advantage that it uses easy available and inexpensive substrates.1 Introduction2 Indole Scaffold Synthesis2.1 Activated Substrates2.2 Unactivated Substrates3 Functionalization of Indole Scaffold3.1 Activated Substrates3.2 Unactivated Substrates4 Conclusions

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Section: Scheme 3 2-chlorophenyl Triflates As Versatile Substrates Tomentioning

confidence: 99%

Pd-Catalyzed Domino Reactions Involving Alkenes To Access Substituted Indole Derivatives

et al. 2020

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“…The terminating step consisted in a Michael addition at the 3-position of the indole furnishing products in 40-89 % yields (Scheme 91). 138 Compounds bearing the (3-indolyl)ethyl moiety were challenging synthetic targets due to the diversity of biologically active tryptamine analogues. 139 Scheme 91.…”

Section: Scheme 87 Synthesis Of Functionalized Imidazolesmentioning

confidence: 99%

Recent Development in Palladium-Catalyzed Domino Reactions: Access to Materials and Biologically Important Carbo- and Heterocycles

2019

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The chemistry of palladium complexes has no limits. Many domino processes (even multicomponent) are continuously appearing in the literature. Carbocyclic and heterocyclic molecules are efficiently prepared under the atom economy principle using the smallest amount of the catalyst. The importance of the applications in many scientific areas of all these cyclic skeletons made this general methodology much more attractive.

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“…Solé and co-workers reported a domino four-step aza-Michael/α-arylation/Michael addition/β-elimination strategy to achieve 3-[2-(phenylsulfonyl)ethyl]indoles (Scheme 29) [54]. From the results of a previous similar synthesis of tetrahydroisoquinolines [55], the authors knew that, conversely from acrylates, the competitive Heck reaction did not interfere with the initial aza-Michael addition and that the sulfone α-arylation was the most important step to be optimized.…”

Section: Palladiummentioning

confidence: 99%

Recent Progress in the Transition Metal Catalyzed Synthesis of Indoles

Mancuso

Dalpozzo

2018

Catalysts

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Indole is the most frequently found heterocyclic core structures in pharmaceuticals, natural products, agrochemicals, dyes and fragrances. For about 150 years, chemists were absorbed in finding new and easier synthetic strategies to build this nucleus. Many books and reviews have been written, but the number of new syntheses that appear in the literature, make necessary continuous updates. This reviews aims to give a comprehensive overview on indole synthesis catalyzed by transition metals appeared in the literature in the years 2016 and 2017.

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Pd-Catalyzed α-Arylation of Sulfones in a Three-Component Synthesis of 3-[2-(Phenyl/methylsulfonyl)ethyl]indoles

Cited by 18 publications

References 87 publications

Pd-Catalyzed Domino Reactions Involving Alkenes To Access Substituted Indole Derivatives

Pd-Catalyzed Domino Reactions Involving Alkenes To Access Substituted Indole Derivatives

Recent Development in Palladium-Catalyzed Domino Reactions: Access to Materials and Biologically Important Carbo- and Heterocycles

Recent Progress in the Transition Metal Catalyzed Synthesis of Indoles

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