Copper-Catalyzed Vinylation of Hydrazides. A Regioselective Entry to Highly Substituted Pyrroles

Rivero, Marta Rodríguez; Buchwald, Stephen L.

doi:10.1021/ol062978s

Cited by 129 publications

(24 citation statements)

References 22 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…1 H NMR (500 MHz, CDCl 3 ) δ 7.35 (d, J.8.2 Hz, 2H, Ar), δ 7.24 (d,J 8.2 Hz,2H,Ar),10H,Ar),6.95 (s,1H,2H,Ar),6.82 (d,2H,J 8.0 Hz, Ar), 6.78 (br, 1H, -NH), 2.43 (s, 3H, -CH 3 ), 2.29 (s, 3H, -CH 3 ). 13 C-NMR (125 MHz, CDCl 3 ): δ 142.…”

Section: -(4-methylphenyl)-34-diphenyl-2-tosylaminopyrrole (5b)mentioning

confidence: 99%

“…1 H-NMR (500 MHz, CDCl 3 ): δ 7. 4H,Ar),1H,Ar);5H,Ar),2H,Ar),1H,Ar),7.00 (t,1H,J 7.9 Hz, Ar), 6.98 (s, 1H, pyrrole-H), 6.89 (d,2H,J 8.1 Hz,Ar),2H,Ar),6.72 (br, 1H, -NH), 2.32 (s, 3H, -CH 3 ). 13 C-NMR (125 MHz, CDCl 3 ): δ 143.…”

Section: -(2-methylphenyl)-34-diphenyl-2-tosylaminopyrrole (5c)mentioning

confidence: 99%

“…Solid (mp 163-165 o C). 1 H-NMR (500 MHz, CDCl 3 ): δ 7.50-7.45 (m, 4H, Ar), 7.40-7.37 (m, 1H, Ar); 7.22 (d,J 8.2 Hz,2H,Ar),7.11 (br,1H,6H,Ar),6.94 (s,1H, (m, 4H, Ar), 2.31 (s, 6H, -2CH 3 ). 13 C-NMR (125 MHz, CDCl 3 ): δ 143.…”

Section: -(2-methylphenyl)-34-diphenyl-2-tosylaminopyrrole (5c)mentioning

confidence: 99%

See 2 more Smart Citations

Synthesis of multisubstituted pyrroles via a CuI-catalyzed three-component coupling and a 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) / silica-gel promoted cyclization

Chen¹,

Jin²,

Zhu³

et al. 2012

Arkivoc

View full text Add to dashboard Cite

show abstract

Section: -(4-methylphenyl)-34-diphenyl-2-tosylaminopyrrole (5b)mentioning

confidence: 99%

Section: -(2-methylphenyl)-34-diphenyl-2-tosylaminopyrrole (5c)mentioning

confidence: 99%

See 1 more Smart Citation

Synthesis of multisubstituted pyrroles via a CuI-catalyzed three-component coupling and a 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) / silica-gel promoted cyclization

Chen¹,

Jin²,

Zhu³

et al. 2012

Arkivoc

View full text Add to dashboard Cite

show abstract

“…Addition of the latter to a dicarbonyl 306 is followed by either reductive elimination or protonation to afford 309 and 312. The latter undergoes a dehydration-hydration sequence to give formamidine 313, which, upon Rh-catalyzed decarbonylation (314) and cyclocondensation, produces the corresponding pyrrole 308 (Scheme 8.110). The regioselective addition of Rh-species 310 across unsymmetrical 1,3-dione 306 is dictated by stereo-and/or electronic effects of substituents at the carbonyl groups in 1,3-diketone 306.…”

Section: %mentioning

confidence: 99%

“…In addition, previously unreactive 1,3-diketones 335 could serve as feasible 1,3-dicarbonyl components in this formal [ Buchwald disclosed a domino approach to pyrroles based on the Piloty-Robinson synthesis involving [3,3]-rearrangement of divinylhydrazides 341. The latter key intermediates were accessed via two sequential Cu(I)-catalyzed vinylations of bisBoc-hydrazine 338 (Scheme 8.119) [314]. The scope of this transformation is displayed in Scheme 8.120.…”

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

1,10-Phenanthroline

Correa

Martı́n

2012

Encyclopedia of Reagents for Organic Synthesis

View full text Add to dashboard Cite

Copper-Catalyzed Vinylation of Hydrazides. A Regioselective Entry to Highly Substituted Pyrroles

Cited by 129 publications

References 22 publications

Synthesis of multisubstituted pyrroles via a CuI-catalyzed three-component coupling and a 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) / silica-gel promoted cyclization

Synthesis of multisubstituted pyrroles via a CuI-catalyzed three-component coupling and a 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) / silica-gel promoted cyclization

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

1,10-Phenanthroline

Contact Info

Product

Resources

About