Palladium(0) catalyzed 2,2′-bipyrrole syntheses

Jiao, Lijuan; Hao, Erhong; Fronczek, Frank R.; Vicente, M. Graça H.

doi:10.1142/s1088424611003355

Cited by 7 publications

(6 citation statements)

References 16 publications

(33 reference statements)

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“…Our overall synthesis of dipyrrole ( 4a ) from readily available 2-iodopyrrole ( 1a ) [12] is shown in Scheme 1. First, a three-step sequence (coupling-desilylation-coupling) using trimethylsilylethyne as the source of the 2-atom alkynyl bridge was used, as previously described [13].…”

Section: Resultsmentioning

confidence: 99%

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Efficient synthesis and reactions of 1,2-dipyrrolylethynes

Tanui

Hao

Ihachi

et al. 2011

J. Porphyrins Phthalocyanines

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Various dipyrroles possess important motifs for construction of pyrrole-containing pigments. A series of 1,2-dipyrrolylethynes (4a–d) has been efficiently synthesized using an improved one-pot double Sonagashira coupling from trimethylsilylethyne and various 2-iodopyrroles. The resulting 1,2-dipyrrolylethynes were further transformed into novel indolyl-, ethenyl- and carboranyl-dipyrroles (5–7) using the Larock indole synthesis, stereoselective catalytic hydrogenation, or B10H14. Indolyl-dipyrroles were found to selectively bind fluoride ions using one pyrrolic and the indolyl NHs, whereas the carboranyl- and ethenyl-dipyrroles are potentially valuable precursors for the synthesis of porphyrin isomers and expanded pigments.

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Section: Resultsmentioning

confidence: 99%

“…MALDI-TOF mass spectra were obtained on an Applied Biosystems QSTAR XL instrument, using positive mode with dithranol as matrix unless otherwise indicated. Compounds 1a – c were prepared according to the literature [12]. UV-visible absorption spectra and fluorescence emission spectra were recorded on commercial spectrophotometers.…”

Section: Methodsmentioning

confidence: 99%

Efficient synthesis and reactions of 1,2-dipyrrolylethynes

Tanui

Hao

Ihachi

et al. 2011

J. Porphyrins Phthalocyanines

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“…An alternative method for synthesis of 2,2′-bipyrroles that avoids use of the Ullmann coupling was developed in 2007 by Smith and co-workers. , In this reaction, copper is replaced by a catalytic system consisting of Pd/C and zinc. The coupling occurs smoothly, starting from β,β′-substituted 2-iodopyrroles bearing formyl, , ester, and nitrile groups in mixtures of toluene/water or acetone/water at room temperature in moderate yields. The main advantage of this protocol is the simplified synthesis of functionalized bipyrrole dialdehydes such as 64 , which are ready to participate in McMurry coupling to afford etioporphycenes (Scheme ).…”

Section: Porphycenesmentioning

confidence: 99%

Porphycenes and Related Isomers: Synthetic Aspects

Anguera

Sánchez‐García

2016

Chem. Rev.

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Porphyrins, called the pigments of life, have been studied for decades. However, the first constitutional isomer of porphyrin, porphycene, was not synthesized until 1986. This milestone marked the beginning of a new era in the field of porphyrinoids and presented opportunities for the creation of an abundance of new pigments. The unique structural and electronic features of these compounds give rise to interesting physical and optical properties with applications in biomedicine and materials science. This review focuses on the synthetic methodologies available for the preparation of porphycenes (functionalized porphycenes, extended porphycenes, benzoporphycenes, naphthoporphycenes, and heteroanalogues) and the other known isomers, namely, corrphycene, hemiporphycene, and isoporphycene. Although the classical synthetic approaches are discussed, particular emphasis is placed on improvements to the known methodologies and recent advances in the field.

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“…However, reaction temperature higher than 100 °C and prolonged reaction time are not compatible with relatively reactive functional groups. Smith and co-workers , reported Pd-catalyzed dehalogenative homocoupling using activated Zn powder that proceeded effectively under ambient temperature even without N-Boc protection. Such mild reaction conditions allowed 2-formylpyrroles to be used directly, leading to moderate yield of 5,5′-diformyl-2,2′-bipyrrole 2 (Scheme ).…”

Section: Synthesis Of Bipyrroles and Oligopyrrolesmentioning

confidence: 99%

2,2′-Bipyrrole-Based Porphyrinoids

Setsune

2016

Chem. Rev.

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A large number of porphyrinoids containing 2,2'-bipyrrole subunits have appeared since they were originally found as a component of sapphyrin and corrole, and it was found that the bipyrrole subunit endowed macrocycles with specific geometric features and electronic properties. Synthetic methods for bipyrrole-containing precursors for porphyrinoid are summarized in this review; these include coupling reactions of pyrrole rings, pyrrole ring-forming reactions leading directly to bipyrrole units, and synthetic reactions for oligopyrrolic compounds. Some hybrid oligopyrroles having nonpyrrole (hetero)aromatic ring(s) are also included. This review also describes porphyrinoids composed of bipyrrole subunits. Interesting electronic properties derived from strong cyclo-π-conjugation are highlighted in the bipyrrole-based porphyrinoids with or without meso-like carbons. Anion-binding chemistry is one of the main topics for bipyrrole-based macrocycles with less efficient or deficient cyclo-π-conjugation, such as those linked with electronically localized aromatic ring(s), with sp carbon(s), and with amido or imine connection(s). The principal concern in this review is porphyrinoids of relatively large ring size, composed of more than five units of pyrroles and (hetero)aromatic substitutes in total, and so bipyrrole-based porphyrinoids up to five pyrrolic units, such as corroles, porphycenes, sapphyrins, and smaragdyrin, will not be covered here except for some special cases.

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Palladium(0) catalyzed 2,2′-bipyrrole syntheses

Abstract: Several 2-iodopyrroles are used in Pd(0) catalyzed homocoupling reactions at room temperature in the presence of water to efficiently synthesize 2,2′-bipyrroles. These 2,2′-bipyrroles are strongly luminous materials and have high fluorescence quantum yields.

Cited by 7 publications

References 16 publications

Efficient synthesis and reactions of 1,2-dipyrrolylethynes

Efficient synthesis and reactions of 1,2-dipyrrolylethynes

Porphycenes and Related Isomers: Synthetic Aspects

2,2′-Bipyrrole-Based Porphyrinoids

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