<i>N</i>-Heterocyclic Carbene-Catalyzed Cross-Coupling of Aldehydes with Arylsulfonyl Indoles

Li, Yang; Shi, Fuqiang; He, Qing‐Li; You, Shu‐Li

doi:10.1021/ol9013238

Cited by 69 publications

(21 citation statements)

References 66 publications

(16 reference statements)

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“…You demonstrated the coupling of aryl aldehydes with arylsulfonyl-indoles. 100 The reaction proceeds via initial expulsion of tosylate by the enamine, generating the corresponding α,β-unsaturated iminium ion, which acts as the Michael acceptor for the intermolecular Stetter reaction. A broad range of aryl aldehydes perform well, but aliphatic aldehydes deliver the products in lower yield.…”

Section: Umpolung Acyl-anion Catalysismentioning

confidence: 99%

Organocatalytic Reactions Enabled by N-Heterocyclic Carbenes

et al. 2015

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Section: Umpolung Acyl-anion Catalysismentioning

confidence: 99%

Organocatalytic Reactions Enabled by N-Heterocyclic Carbenes

et al. 2015

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“…After our report on the reaction of aldehydes with sulfonyl indoles, a Stetter‐like process using a thiazolium salt as an organocatalyst appeared in the literature (Scheme ) 53…”

Section: Reaction With Enolate Systemsmentioning

confidence: 99%

Sulfonyl Azoles in the Synthesis of 3-Functionalized Azole Derivatives

Palmieri

Petrini

2016

The Chemical Record

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Sulfonyl indoles, as well as related azolyl derivatives, have been recently introduced in synthesis as stable precursors of reactive indolenine intermediates. This personal account reports on the discovery of sulfonyl azoles and their practical utilization in many synthetic processes for the preparation of functionalized 3-substituted indoles, indazoles, and pyrroles. The indolenine intermediates obtained by treatment of sulfonyl azoles with Brønsted bases or Lewis acids can be considered as vinylogous imino derivatives that can be made to react with different nucleophilic reagents. These include organometallic reagents, reducing agents, stabilized carbanions, and heteronucleophiles. The controlled and mild conditions for the generation of indolenines from sulfonyl azoles make these substrates particularly useful in asymmetric synthesis, exploiting organo- or metal-catalyzed processes. Although less exploited, sulfonyl indoles can also be involved in photochemical processes for the preparation of polycyclic derivatives.

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“…108 The optimization for a racemic procedure revealed 3-benzyl-5-(2-hydroxyethyl)-4-methylthiazolium chloride to be a highly effective precatalyst. However, attempts to use a chiral N-heterocyclic carbene as catalyst gave very poor yields albeit with very good enantioselectivity (Scheme 75).…”

Section: -Indolyl(aryl)sulfonylmethanesmentioning

confidence: 99%