Multicomponent Tandem Triple Functionalization of Indoles via a Directing‐group‐free Strategy

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(7), С. 990 - 996

Опубликована: Март 14, 2023

Abstract The position‐selective functionalization of the poorly reactive benzenoid nucleus indoles has remained a great challenge in organic chemistry. Here we describe directing‐group‐free, three‐component tandem C3‐acylation/C5,6‐H disulfenylation via an iodine‐, Lewis acid‐ and Brønsted acid‐cooperated mediated strategy. This protocol is remarkable for its exceptional regio‐ chemo‐selectivity, broad substrate scope, good functional group tolerance mild reaction conditions. Advantageously, present offers potential development general site‐selective at indoles, removing requirement neighbouring activating groups. magnified image

Язык: Английский

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Chiral-Phosphoric-Acid-Catalyzed C6-Selective Pictet–Spengler Reactions for Construction of Polycyclic Indoles Containing Spiro Quaternary Stereocenters

Organic Letters, Год журнала: 2022, Номер 24(8), С. 1727 - 1731

Опубликована: Фев. 24, 2022

Compared with the well-established asymmetric Pictet-Spengler reactions on pyrrole ring of indoles, catalytic reaction benzene indoles has been rarely studied. Herein C6-selective have realized by employing 2-(1H-indol-7-yl)anilines and isatins in presence chiral phosphoric acid, affording novel polycyclic indole derivatives bearing spiro quaternary stereocenters excellent yields enantioselectivities. This could be conducted gram scale without any loss activity or enantioselectivity.

Язык: Английский

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A Study of the Reactivity of (Aza‐)Quinone Methides in Selective C6‐Alkylations of Indoles

ChemCatChem, Год журнала: 2020, Номер 12(20), С. 5053 - 5057

Опубликована: Июль 28, 2020

Abstract The kinetic and thermodynamic features of indole N1‐ C6‐alkylation reactions with (aza‐)quinone methides have been studied. electrophilic reactivity these quinone also compared for the first time by both experiments DFT calculations. N1‐alkylation is typically kinetically favorable, but more thermodynamically favorable. With suitable conditions, could be achieved high efficiency selectivity. Among methides, increases from aza‐p‐QMs to o‐QMs. results not only provide access a range valuable triarylmethanes, guide future development new versatile electrophiles.

Язык: Английский

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Palladium-Catalyzed C2-Regioselective Perfluoroalkylation of the Free (NH)-Heteroarenes

The Journal of Organic Chemistry, Год журнала: 2021, Номер 86(3), С. 2840 - 2853

Опубликована: Янв. 12, 2021

A highly regioselective and atom-efficient strategy for the construction of fused free (NH) heteroarenes through a palladium-catalyzed perfluoroalkyl insertion reaction has been accomplished. This protocol employed multiple iodofluoroalkanes as practical available sources to provide an operationally simple versatile route synthesis perfluoroalkylated indoles. Moreover, indoles without assistance guide groups were utilized substrates, achieving C(sp2)–H site-selective functionalization in yields up 95%. Furthermore, this was also used late-stage C2 perfluoroalkylation bioactive compounds such auxin, tryptophan, melatonin analogues.

Язык: Английский

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De novo three-component synthesis of meta-substituted anilines

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(11), С. 2760 - 2765

Опубликована: Янв. 1, 2023

A metal- and additive-free reaction of easily accessible N -acylpyridinium iodides, methylvinyl ketones amines provides access to meta -substituted anilines.

Язык: Английский

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