Rhodium-Catalyzed C-C Bond Cleavage Reactions

Nečas, David; Kotora, Martin

doi:10.2174/138527207782418645

Cited by 157 publications

(17 citation statements)

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“…Accordingly, a detailed discussion of recent contributions to the area of furan synthesis via these two routes is presented below. Transition metal-catalyzed cycloisomerization of allenyl ketones into furan products was first introduced by Marshall. In the first report from this group, it was demonstrated that various alkyl-substituted furans 2 could be prepared in high yields via the Ag- [50] or the Rh(I)-catalyzed [85,86] cycloisomerization of allenyl ketones 1 (Scheme 8.1) [87]. This type of transformation of allenyl ketones [88][89][90] proved to be highly efficient for the synthesis of up-to-trisubstituted furans.…”

Section: Furansmentioning

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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Section: Furansmentioning

confidence: 99%

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

Dudnik

Gevorgyan

2010

Catalyzed Carbon‐Heteroatom Bond Formation

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“…29 It was demonstrated that various alkyl-substituted furans 2-2 could be prepared in high yields via the Ag- 4b or the Rh(I)-catalyzed 30 cycloisomerization of allenyl ketones 2-1 (Scheme 1). …”

Section: Synthesis Of Furansmentioning

confidence: 99%

Transition Metal-Mediated Synthesis of Monocyclic Aromatic Heterocycles

et al. 2013

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“…[2] A well-known example is methyltrioxorhenium (MTO), [3] which catalyzes hydroxylation of aromatic and saturated hydrocarbons in the presence of pyrazin-2-carboxylic acid. [4] Rhodium derivatives [5] have been used in various catalytic processes, for example, in hydroformylation and hydroaminomethylation, [6] hydrosilylation, [7] hydrogenation and isomerization, [8] transfer hydrogenation with formic acid, [9] C-C bond cleavage reactions, [10] addition of aldehydes to olefins, [11] carboxylation of arenes, [12] C-H activation [13] and asymmetric addition to olefins. [14] Rhodium carbonyls are efficient promoters in some catalytic processes.…”

Section: Introductionmentioning

confidence: 99%