<i>C</i>-Vinylpyrroles as Pyrrole Building Blocks

Трофимов, Б. А.; Собенина, Л. Н.; Demenev, and Andrey P.; Михалева, А. И.

doi:10.1021/cr020100i

Cited by 167 publications

(49 citation statements)

References 121 publications

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“…During the development of a Lewis acid-catalyzed variant of the Trofimov reaction, 88 it was shown that among lanthanide(III) salts screened Eu(OTf) 3 offered superior catalytic activity and provided an efficient method for accessing polyfunctionalized pyrroles 114 (Scheme 33). 89 The Eu(OTf) 3 -promoted Trofimov pyrrole synthesis exhibited broad reaction scope with a wide range of aromatic, heteroaromatic and aliphatic side-chains tolerated.…”

Section: Scheme 32 Synthesis Of Spirocycles 111mentioning

confidence: 99%

Recent applications of rare-earth metal(III) triflates in cycloaddition and cyclization reactions

Ladziata¹

2014

Arkivoc

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Rare-earth metal(III) triflates are extremely mild, efficient and water-tolerable Lewis acid catalysts for a wide range of organic transformations. Rare-earth metal triflates retain activity even in the presence of multiple Lewis bases containing oxygen, nitrogen, sulfur and phosphorus atoms, and can be easily recovered and reused without any loss of catalytic activity. This review summarizes recent developments and highlights key applications of these unique Lewis acids in cycloaddition and cyclization reactions.

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Section: Scheme 32 Synthesis Of Spirocycles 111mentioning

confidence: 99%

Recent applications of rare-earth metal(III) triflates in cycloaddition and cyclization reactions

Ladziata¹

2014

Arkivoc

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“…C-Vinylpyrroles are useful in various applications, for example cycloaddition reactions (Section 4.5.7), and comprehensive reviews highlighting the preparation [571] and synthetic uses of these compounds have appeared quite recently [572].…”

Section: Pyrryl-c-x Compounds: Synthesis and Reactionsmentioning

confidence: 99%

Five‐Membered Heterocycles: Pyrrole and Related Systems

Bergman

Janosik

2011

Modern Heterocyclic Chemistry

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“…In addition, the pyrrole framework represents some interest as a synthon, allowing access to various essential structures [66,68,[249][250][251][252][253][254]. Quite expectedly, a great interest caused by the importance and valuable properties of pyrroles is reflected in a number of excellent reviews on the synthesis of the pyrrole framework appearing recently in the literature [83,237,242,246,248,[255][256][257][258][259][260][261][262][263][264][265].…”

Section: Pyrrolesmentioning

confidence: 99%

Transition Metal‐Catalyzed Synthesis of Monocyclic Five‐Membered Aromatic Heterocycles

Dudnik

Gevorgyan

2010

Catalyzed Carbon‐Heteroatom Bond Formation

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Aromatic heterocycles, particularly furans and pyrroles, are structural motifs found in a vast number of biologically active natural and artificial compounds [1][2][3]. Other examples of practical applications of furans and pyrroles include dyes, polymers, and electronic materials [4]. Moreover, these heterocycles are employed as important intermediates in organic synthesis [5][6][7][8][9]. The successful application of furans and pyrroles in these and many other ways and their significance in applied and fundamental areas have placed them at the forefront of contemporary organic chemistry. A variety of methodologies and different protocols for their synthesis have been reported [1-3, 10-23] and become well established throughout decades. Among the variety of novel approaches for the synthesis of furans and pyrroles, transition metal-catalyzed transformations are arguably the most attractive methodologies . Several excellent reviews on the transition metal-catalyzed synthesis of monocyclic five-membered heterocycles have been published in the literature. Many of them were categorized by either the metal or the type of transformation. This chapter covers transition metal-catalyzed syntheses of furans and pyrroles. The main organization of this chapter is based on a heterocycle, wherein syntheses of a particular core are structured by the type of transformation and substrates engaged. Herein, we have tried to discuss equally the synthetic applicability of a method and mechanistic aspects and concepts implicated in the described transformations. A discussion of the mechanisms is given when needed to provide an idea about possible reaction pathways and the nature of the elementary processes involved in the catalytic transformation. It should be noted that the most essential and general catalytic reactions, as well as recent and conceptionally interesting transformations, are discussed in more detail in this chapter. Syntheses of furans and pyrroles via functionalization of the preexisting heterocyclic cores [37,[52][53][54][55][56][57][58][59][60] are not covered and, therefore, only reactions in which assembly of a heterocyclic ring occurs are described. In addition, the Pd-catalyzed synthesis of heterocycles is not covered herein, as this topic is covered in Chapter 6.

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C-Vinylpyrroles as Pyrrole Building Blocks

Cited by 167 publications

References 121 publications

Recent applications of rare-earth metal(III) triflates in cycloaddition and cyclization reactions

Recent applications of rare-earth metal(III) triflates in cycloaddition and cyclization reactions

Five‐Membered Heterocycles: Pyrrole and Related Systems

Transition Metal‐Catalyzed Synthesis of Monocyclic Five‐Membered Aromatic Heterocycles

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