(η4-1,5-Cyclooctadiene)(η6-phosphinine)iron(0):  Novel Room-Temperature Catalyst for Pyridine Formation,1

Knoch, Falk; Kremer, Frank; Schmidt, and Uwe; Zenneck, Ulrich; and, Pascal Le Floch; Mathey, François

doi:10.1021/om950800w

Cited by 106 publications

(53 citation statements)

References 30 publications

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“…Breit et al [4] have shown that substituted phosphinines coordinated in a h 1 fashion to rhodium can act as highly activated and selective catalysts for the hydroformylation of olefins. Likewise, complexes containing h 6 -phosphinines catalyse the synthesis of pyridines from alkynes and nitriles [5] and the cyclodimerisation of 1,3-butadiene. [6] In previous studies [7][8][9][10] we showed that the 2,4,6-tri-tertbutyl-1,3,5-triphosphabenzene, P 3 C 3 tBu 3 (1 a), readily undergoes [1 + 4] cycloaddition reactions with isoelectronic silylenes and (transition-metal-complexed) phosphinidenes (and in unpublished work [11] ) with isolobal In I and Ga I compounds.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of the 2,4,5‐Tri‐tert‐butyl‐1,3‐diphospholide Anion by Phosphinidene Elimination from 2,4,6‐Tri‐tert‐butyl‐1,3,5‐triphosphabenzene on Treatment with the Amide Li[NPh(SiMe₃)]

Clendenning

Hitchcock

Läppert

et al. 2007

Chemistry A European J

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Treatment of the lithium amide Li[NPh(SiMe3)] with 2,4,6-tri-tert-butyl-1,3,5-triphosphabenzene, P(3)C(3)tBu(3), in a 1:2 ratio afforded equimolar amounts of the lithium salt of the five-membered 2,4,5-tri-tert-butyl-1,3-diphospholide anion, LiP(2)C(3)tBu(3) (isolated as its N,N,N',N'-tetramethylethylenediamine (TMEDA) adduct), and the tricyclic compound 6-[phenyl(trimethylsilyl)amino]-3,5,7-tri-tert-butyl-1,2,4,6-tetraphosphatricyclo[3.2.0.0(2,7)]hept-3-ene. Both compounds have been structurally characterised by single-crystal X-ray diffraction studies. The mechanism of this remarkable reaction has been elucidated by theoretical methods at the B3LYP/6-311+G** level of theory. The reaction involves a hitherto unobserved aminophosphinidene, which was formed by abstraction of a phosphorus atom from triphosphabenzene. The intermediate aminophosphinidene, which is further stabilised by the solvent THF, shows, in agreement with previous theoretical predictions, enhanced stability and reacts then with a second molecule of triphosphabenzene.

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Section: Introductionmentioning

confidence: 99%

“…Owing to the greater reactivity of the sodium amide compared with the corresponding lithium reagent, the progress of the reaction was monitored by 5 ] and P 3 C 3 tBu 3 . [10,11] The reaction was complete after 3 days at room temperature, yielding, as expected, NaP 2 C 3 tBu 3 (singlet, d P = 187.4 ppm in THF) and the tricyclic compound 4 a.…”

mentioning

confidence: 99%

Synthesis of the 2,4,5‐Tri‐tert‐butyl‐1,3‐diphospholide Anion by Phosphinidene Elimination from 2,4,6‐Tri‐tert‐butyl‐1,3,5‐triphosphabenzene on Treatment with the Amide Li[NPh(SiMe₃)]

Clendenning

Hitchcock

Läppert

et al. 2007

Chemistry A European J

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“…5,6 During the course of our investigations on functionalized phosphabenzenes, a novel methylthio substituted phosphinine has been prepared. Single crystals of this compound were obtained, which were subject to an X-ray crystal structure analysis.…”

Section: Introduction λmentioning

confidence: 99%

4-(p-Methylthio)phenyl-2,6-diphenyl phosphinine: The first X-ray crystal structure of a λ3-triaryl-phosphabenzene

et al. 2006

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The new donor functionalized methylthio-phosphabenzene 3 was synthesized by reaction of the corresponding pyrylium salt with P(SiMe 3 ) 3 . This compound was characterized crystallographically, showing eight independent molecules in the asymmetric unit. 3 crystallized in the orthorhombic space group Pna2 1 (no. 33) with cell parameters a = 48.3565(8)Å, b = 7.64784(7)Å, c = 40.8432(4)Å, V = 15104.7(3)Å 3 . This result represents the first crystal structure analysis of a λ 3 -triaryl-phosphabenzene.

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“…Zenneck and co-workers [80] developed an Fe(0) complex 42 catalyzed [2+2+2] cycloaddition of two molecules of alkynes and nitriles (Scheme 35), however, this approach gave low chemoselectivity (benezenes were the main products) and had a complicated procedure for catalyst preparation. A stoichiometric reaction between an Fe(+1) complex and alkynes was report by Guerchais and co-workers [81] with high chemoselectivity (Scheme 36).…”

Section: Scheme 34mentioning

confidence: 99%

Recent advances in the iron-catalyzed cycloaddition reactions

Wang

Wan

2012

Chin. Sci. Bull.

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The rapid generation of molecular in a relatively easy manner has made the cycloaddition reaction a powerful tool in the synthesis of different membered ring compounds. Clearly, iron catalysts are becoming a much more interesting and viable choice for this purpose. In this review, a number of promising results in the iron catalyzed cycloaddition reactions in the last decades were summarized. Special attention has been paid to the asymmetric cycloaddition reactions. cycloaddition, iron catalyst, asymmetric Citation:Wang C X, Wan B S. Recent advances in the iron-catalyzed cycloaddition reactions. Chin Sci Bull, 2012, 57: 23382351, doi: 10.1007/s11434-012-5141-z Cycloaddition reaction, which can construct several bonds simultaneously in a single step, is one of the most powerful strategies for the synthesis of cyclic compounds from various unsaturated substrates such as alkynes, alkenes, allenes, nitriles, aldehydes, ketones, imines, etc. Three-, four-, five-, six-or seven-membered rings are obtained through these transformations. The high atom-efficiency, as well as the good tolerance of different functional groups, continues to draw many chemists' attention to this field. In particular, great efforts have been devoted to the development of novel and efficient catalytic systems. However, harsh reaction conditions are often required including heat, light, high pressure or sonication, and the lack of chemo-and/or regioselectivity is also an important problem. Over the past decades, the use of transition metal catalysts has contributed significantly to the development of the cycloaddition reactions and good selectivities were obtained [1]. Among all the available transition metals, iron is generally regarded as one of the most inexpensive, abundant, benign and relatively non-toxic metals [2]. Many transformations have been effectively promoted by iron catalysts, and excellent reviews on the iron-catalyzed reactions are available [3][4][5][6][7][8][9][10][11][12][13][14][15]. Bolm and co-workers [3] summarized the most important transformations with the aid of iron catalysts in 2004, including addition, substitution, cycloaddition, reduction and other reactions. At a later time, they also reviewed the oxidative C-C coupling reactions [4] and the development of carbon-heteroatom and heteroatom-heteroatom bond formation under iron catalysts [5]. The uses of FeCl 3 as catalyst in organic synthesis were covered by Padrón [6] and Bolm [4], and the cross coupling reactions were discussed in detail by Fürstner [7,8]. Recently, direct C-H transformation via iron catalysis was summarized by Shi and co-workers [9]. Applications of iron catalysts on other reactions were also summarized by Bauer [10] However, despite the aforementioned contributions, reviews mainly focus on the iron-catalyzed cycloaddition reactions are rather rare [15]. In this review, we will point out recent advances in this field, most contributions going from 2004 to Nov. 2011. Although every effort has been made to avoid repetition, some overlap with the ...

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(η⁴-1,5-Cyclooctadiene)(η⁶-phosphinine)iron(0): Novel Room-Temperature Catalyst for Pyridine Formation^,¹

Cited by 106 publications

References 30 publications

Synthesis of the 2,4,5‐Tri‐tert‐butyl‐1,3‐diphospholide Anion by Phosphinidene Elimination from 2,4,6‐Tri‐tert‐butyl‐1,3,5‐triphosphabenzene on Treatment with the Amide Li[NPh(SiMe₃)]

Synthesis of the 2,4,5‐Tri‐tert‐butyl‐1,3‐diphospholide Anion by Phosphinidene Elimination from 2,4,6‐Tri‐tert‐butyl‐1,3,5‐triphosphabenzene on Treatment with the Amide Li[NPh(SiMe₃)]

4-(p-Methylthio)phenyl-2,6-diphenyl phosphinine: The first X-ray crystal structure of a λ3-triaryl-phosphabenzene

Recent advances in the iron-catalyzed cycloaddition reactions

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(η4-1,5-Cyclooctadiene)(η6-phosphinine)iron(0): Novel Room-Temperature Catalyst for Pyridine Formation,1

Cited by 106 publications

References 30 publications

Synthesis of the 2,4,5‐Tri‐tert‐butyl‐1,3‐diphospholide Anion by Phosphinidene Elimination from 2,4,6‐Tri‐tert‐butyl‐1,3,5‐triphosphabenzene on Treatment with the Amide Li[NPh(SiMe3)]

Synthesis of the 2,4,5‐Tri‐tert‐butyl‐1,3‐diphospholide Anion by Phosphinidene Elimination from 2,4,6‐Tri‐tert‐butyl‐1,3,5‐triphosphabenzene on Treatment with the Amide Li[NPh(SiMe3)]

4-(p-Methylthio)phenyl-2,6-diphenyl phosphinine: The first X-ray crystal structure of a λ3-triaryl-phosphabenzene

Recent advances in the iron-catalyzed cycloaddition reactions

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Product

Resources

About

(η⁴-1,5-Cyclooctadiene)(η⁶-phosphinine)iron(0): Novel Room-Temperature Catalyst for Pyridine Formation^,¹

Synthesis of the 2,4,5‐Tri‐tert‐butyl‐1,3‐diphospholide Anion by Phosphinidene Elimination from 2,4,6‐Tri‐tert‐butyl‐1,3,5‐triphosphabenzene on Treatment with the Amide Li[NPh(SiMe₃)]

Synthesis of the 2,4,5‐Tri‐tert‐butyl‐1,3‐diphospholide Anion by Phosphinidene Elimination from 2,4,6‐Tri‐tert‐butyl‐1,3,5‐triphosphabenzene on Treatment with the Amide Li[NPh(SiMe₃)]