Oligosubstituted Pyrroles Directly from Substituted Methyl Isocyanides and Acetylenes

Lygin, Alexander V.; Larionov, Oleg V.; Korotkov, Vadim S.; Meijere, Armin de

doi:10.1002/chem.200801395

Cited by 101 publications

(51 citation statements)

References 141 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…However, following the initial report in 1979, 79 there was a long period of silence. 82 Obviously, this approach was not practical. Unfortunately, this protocol was not applicable to more abundant, non-activated terminal alkynes.…”

Section: Cycloaddition and Cyclizationmentioning

confidence: 99%

Silver-catalysed reactions of alkynes: recent advances

2015

View full text Add to dashboard Cite

Silver is a less expensive noble metal. Superior alkynophilicity due to π-coordination with the carbon-carbon triple bond makes silver salts ideal catalysts for alkyne-based organic reactions. This review highlights the progress in alkyne chemistry via silver catalysis primarily over the past five years (ca. 2010-2014). The discussion is developed in terms of the bond type formed with the acetylenic carbon (i.e., C-C, C-N, C-O, C-Halo, C-P and C-B). Compared with other coinage metals such as Au and Cu, silver catalysis is frequently observed to be unique. This critical review clearly indicates that silver catalysis provides a significant impetus to the rapid evolution of alkyne-based organic reactions, such as alkynylation, hydrofunctionalization, cycloaddition, cycloisomerization, and cascade reactions.

show abstract

Section: Cycloaddition and Cyclizationmentioning

confidence: 99%

Silver-catalysed reactions of alkynes: recent advances

2015

View full text Add to dashboard Cite

show abstract

“…The reaction mechanism is outlined in Scheme 8.112. [310,311]. The best results were achieved with Cu(I) benzenethiolate or preactivated nanosized copper powder (Cu 0 -NP) catalysts.…”

Section: %mentioning

confidence: 74%

“…A recent work from de Meijeres group revealed that this issue can be resolved by employing stoichiometric amounts of a slightly modified Cu(I) system. Accordingly, terminal alkynes 326 were shown to undergo the Cu(I)-mediated formal [ [311].…”

Section: %mentioning

confidence: 99%

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

Dudnik

Gevorgyan

2010

Catalyzed Carbon‐Heteroatom Bond Formation

View full text Add to dashboard Cite

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.

show abstract

“…Several copper could catalyze the polysubstituted pyrrole formation. Moreover, they also developed a new copper catalyst system for the synthesis of 2,3-disubstituted pyrroles by the reaction of copper acetylides derived from unactivated terminal alkynes with substituted methyl isocyanides in 5-88% yield [16,17]. The regiocontrolled formation of pyrroles via a formal [3+2] cycloaddition of isocyanides and electron-deficient alkynes could be realized in different catalytic system.…”

Section: Copper-catalyzed Synthesis Of Pyrrolesmentioning

confidence: 99%