Furans and their Benzo Derivatives: (iii) Synthesis and Applications

Donnelly, Dervilla M. X.

doi:10.1016/b978-008096519-2.00062-x

Cited by 130 publications

(53 citation statements)

References 256 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[2] Thus the synthesis of furans has always been of importance. [3] Since alkynyloxiranes are nowadays easily accessible by either a Sonogashira coupling [4] of an alkyne and a vinyl halide and a subsequent epoxidation [5] or nucleophilic ring closure of propargylic alcohols with a leaving group in the homopropargylic position, [6] the isomerization of alkynyloxiranes to furans looks quite attractive, especially for highly substituted furans.…”

Section: Introductionmentioning

confidence: 99%

Gold Catalysis: Mild Conditions for the Transformation of Alkynyl Epoxides to Furans

Hashmi¹,

Sinha²

2004

Adv Synth Catal

233

View full text Add to dashboard Cite

show abstract

Section: Introductionmentioning

confidence: 99%

Gold Catalysis: Mild Conditions for the Transformation of Alkynyl Epoxides to Furans

Hashmi¹,

Sinha²

2004

Adv Synth Catal

233

View full text Add to dashboard Cite

show abstract

“…In the presence of CuA C H T U N G T R E N N U N G (OTf) 2 or AgSbF 6 , the formation of furan 2a was not observed (entries 1 and 2). Treatment of alkynyloxirane 1a with 2 mol % of PdA C H T U N G T R E N N U N G (OAc) 2 or PtCl 2 gave the desired furan 2a in 13 % and 11 % yields, respectively. However the reaction did not proceed to completion even after 24 h at room temperature (entries 3 and 4).…”

Section: Resultsmentioning

confidence: 99%

“…[2] For this reason, the efficient synthesis of multiply substituted furans continues to attract the interest of synthetic chemists. [3] Among many different approaches to furans, the isomerization of alkynyloxiranes to furans looks quite attractive.…”

Section: Introductionmentioning

confidence: 99%

Gold‐Catalyzed Tandem Cycloisomerization of Alkynyloxiranes with Nucleophiles: An Efficient Approach to 2,5‐Disubstituted Furans

et al. 2007

View full text Add to dashboard Cite

show abstract

“…Furans are highly important five-membered heterocycles, which are incorporated as structural units into a variety of many natural and synthetic biologically-active compounds and materials [61][62][63][64][65]. Moreover, a furan heterocycle itself is of significant interest as a synthon towards an array of valuable intermediates [66][67][68][69][70][71][72][73].…”

Section: Furansmentioning

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

Furans and their Benzo Derivatives: (iii) Synthesis and Applications

Cited by 130 publications

References 256 publications

Gold Catalysis: Mild Conditions for the Transformation of Alkynyl Epoxides to Furans

Gold Catalysis: Mild Conditions for the Transformation of Alkynyl Epoxides to Furans

Gold‐Catalyzed Tandem Cycloisomerization of Alkynyloxiranes with Nucleophiles: An Efficient Approach to 2,5‐Disubstituted Furans

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

Contact Info

Product

Resources

About