Decarboxylative arylation of substituted pyrroles <i>N</i>-protected with 2-(trimethylsilyl)ethoxymethyl (SEM)

Figliola, Carlotta; Greening, Sarah M.; Lamont, Connor; Groves, Brandon R.; Thompson, Alison

doi:10.1139/cjc-2017-0402

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Can. J. Chem.

2018

DOI: 10.1139/cjc-2017-0402

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Decarboxylative arylation of substituted pyrroles N-protected with 2-(trimethylsilyl)ethoxymethyl (SEM)

Carlotta Figliola

Sarah M. Greening

Connor Lamont

et al.

Abstract: Palladium-catalyzed decarboxylative arylation is reported using pyrroles N-protected with the 2-(trimethylsilyl)ethoxymethyl (SEM) group and featuring 2-, 3-, and 4-substituents about the pyrrolic framework. In contrast to N-protected pyrroles previously used in decarboxylative arylation, the use of SEM allows deprotection under mild conditions.

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Cited by 3 publications

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Dual Role of the Arylating Agent in a Highly C(2)-Selective Pd-Catalysed Functionalisation of Pyrrole Derivatives

Petković¹,

Jovanović²,

Jovanović³

et al. 2022

Synthesis

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Pyrrole derivatives with C(2)-aryl substituents are an important and widespread class of heterocyclic compounds. Their synthesis can be accomplished using several strategic variants which usually entail either protection of the N-H functionality followed by the arylation or a direct arylation. Although direct arylation is a preferable process due to a reduced number of synthetic steps, it often requires vigorous conditions or challenging reagents. To this synthetic repertoire, we added a novel method that is based on the dual role of the arylating agent. It serves as the N-H protecting group while also being involved in the arylation step. Deprotection as a final stage is carried out simultaneously utilizing amines as reacting components. This approach ensures relatively mild conditions and exclusive C(2) selectivity yielding 2-aryl pyrroles with the amide functionality. While the aromatic amines are not suitable partners under studied conditions, most likely due to lower nucleophilicity, aliphatic amines, either primary or secondary, afford products in good yields

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Dual Role of the Arylating Agent in a Highly C(2)-Selective Pd-Catalysed Functionalisation of Pyrrole Derivatives

Petković¹,

Jovanović²,

Jovanović³

et al. 2022

Synthesis

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show abstract

Synthesis of sulfenyl dipyrroles via reaction of α-free pyrroles with thionyl chloride

et al. 2021

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Sulfenyl dipyrroles feature two pyrroles linked via a sulfenyl bridge. The synthesis of sulfenyl dipyrroles has typically involved SCl2 as the sulfur source. However, SCl2 is no longer readily available within North America and Europe. Herein we report a new synthesis of sulfenyl dipyrroles using SOCl2 as the sulfur source and reductant. Although five new sulfenyl dipyrroles were synthesized and isolated via this route, functional group tolerance proved limited. A potential mechanism for the reaction, involving reduction of a sulfinyl moiety by SOCl2, is briefly explored.

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Bacteriochlorin syntheses - Status, problems, and exploration

Tran¹,

Wang²,

Matsumoto³

et al. 2023

J. Porphyrins Phthalocyanines

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Bacteriochlorins – Nature’s near-infrared (NIR) chromophores – are distinguished by an intense ([Formula: see text] [Formula: see text]105 M[Formula: see text]cm[Formula: see text] long-wavelength absorption band in the [Formula: see text]700–1000 nm. The development of routes to prepare synthetic, tailorable bacteriochlorins holds promise for multiple disciplines where NIR-light-promoted photoactivity is of interest. A de novo route to bacteriochlorins equipped with a stabilizing gem-dimethyl group in each pyrroline ring was discovered in 2003. Continued development in this arena over 20 years has led to additional routes as well as methods to install substituents at selected positions about the perimeter of the macrocycle. The present paper reports studies that highlight substantial limitations of existing synthetic routes, including stymied access to multi-bacteriochlorin arrays and the inability to install (in a rational way) distinct groups at opposite sides of the macrocycle. The origins of the limitations are traced to particular stages of the chemistry ranging from derivatizing pyrroles, creating pyrrolines, constructing and elaborating dihydrodipyrrins, coupling dihydrodipyrrins, and forming macrocycles. Through exploration of a dozen aspects of bacteriochlorin syntheses, 60 new compounds (and nine known compounds via improved syntheses) have been prepared and characterized; the data include 20 single-crystal X-ray diffraction analyses. The research taken together points to areas of focus to fulfill the promise of this fascinating class of compounds.

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Decarboxylative arylation of substituted pyrroles N-protected with 2-(trimethylsilyl)ethoxymethyl (SEM)

Cited by 3 publications

References 42 publications

Dual Role of the Arylating Agent in a Highly C(2)-Selective Pd-Catalysed Functionalisation of Pyrrole Derivatives

Dual Role of the Arylating Agent in a Highly C(2)-Selective Pd-Catalysed Functionalisation of Pyrrole Derivatives

Synthesis of sulfenyl dipyrroles via reaction of α-free pyrroles with thionyl chloride

Bacteriochlorin syntheses - Status, problems, and exploration

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