Palladium‐Catalyzed Direct Synthesis of Phosphole Derivatives from Triarylphosphines through Cleavage of Carbon–Hydrogen and Carbon–Phosphorus Bonds

Baba, Katsuaki; Tobisu, Mamoru; Chatani, Naoto

doi:10.1002/anie.201307115

Cited by 148 publications

(69 citation statements)

References 60 publications

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“…[7] We anticipated that applying this methodology to the (unreported) biaryl-phosphine 3 (Scheme 2), in which the P-remote arene ring is part of a conical calix [4]arene skeleton, would result in a calixarene-fused phosphole.…”

Section: Synthesis and Coordinative Properties Of A Phosphole Precursormentioning

confidence: 99%

Calix[4]arene-fused phospholes

et al. 2017

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A calix [4]arene-based biarylphosphine has been synthesised and catalytically converted into two diastereomeric, calixarene-fused phospholes. arene has been prepared and its coordinative properties investigated. When heated in the presence of palladium, the new biarylphosphine undergoes conversion into two diasteromeric, calixarene-fused phospholes. In both, the P lone pair adopts a fixed orientation with respect to the calixarene core. The more hindered phosphole (8), i.e. the one with the endo-oriented lone pair (cone angle 150°-175°), forms complexes having their metal centre positioned very near the calixarene unit but outside the cavity, this inducing an unusual chemical shift of one of the methylenic ArCH 2 Ar protons owing to interactions with the metal centre. As expected for dibenzophospholes, the complex [Rh(acac)(CO)•8], when combined with one equivalent of free 8, efficiently catalyses the hydroformylation of styrene, the catalytic system displaying high regioselectivity in favour of the branched aldehyde (b/l ratio up to 30). The optical and redox properties of the derivatives have also been investigated.

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Section: Synthesis and Coordinative Properties Of A Phosphole Precursormentioning

confidence: 99%

Calix[4]arene-fused phospholes

et al. 2017

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“…This strategy features simplicity, atom economics, high yields, and good functional group compatibility, providing an efficient and versatile entrance to a variety of dibenzophosphole oxides applicable in materials. A palladium-catalyzed method for the synthesis of phospholes from triarylphosphines has been developed by Chatani and coworkers (Scheme 4.26) [41]. The reaction was found to occur in the presence of a catalytic quantity of Pd(OAc) 2 at 160 ∘ C. The condition was very simple.…”

Section: P-c Heterocycles (Dibenzophosphole Oxides)mentioning

confidence: 96%

Pd‐Catalyzed Synthesis of Other Heteroatom‐Containing Heterocycles

Liu

Zhang

2016

Transition Metal‐Catalyzed Heterocycle Synthesis via CH Activation

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“…[9,10] Recently, approaches based on C À Hf unctionalizations have emerged. Alternatively,b iaryls bearing appropriate ortho-substituents (Si, P, S) may undergo an intramolecular heteroatom-aryl bond formation, thus affording dibenzosiloles, [14] dibenzophospholes, [15] or dibenzothiophenes (route C, Scheme 1a). Alternatively,b iaryls bearing appropriate ortho-substituents (Si, P, S) may undergo an intramolecular heteroatom-aryl bond formation, thus affording dibenzosiloles, [14] dibenzophospholes, [15] or dibenzothiophenes (route C, Scheme 1a).…”

Section: Bin Wu and Naohiko Yoshikai*mentioning

confidence: 99%

Conversion of 2‐Iodobiaryls into 2,2′‐Diiodobiaryls via Oxidation‐Iodination Sequences: A Versatile Route to Ladder‐Type Heterofluorenes

Yoshikai

2015

Angewandte Chemie

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Even though 2,2'-diiodo-and 2,2'-dibromobiaryls represent accomplished precursors for heterofluorenes and other extended p-conjugated systems,t heir preparation still remains nontrivial when structural diversity of the biaryl backbone is required. Herein, we report ac onvenient method for the preparation of various 2,2'-diiodobiaryls from 2iodobiaryls via cyclic diaryliodonium intermediates.A ni odinative ring-opening of the diaryliodonium salts,m ediated by ac opper/diamine catalyst system, is able to affordt he corresponding 2,2'-diiodobiaryls under mild conditions.T he versatility of this two-step approachi sd emonstrated by the preparation of hitherto unexplored tetraiodoteraryls and their conversion into ladder-type p-conjugated systems.

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Palladium‐Catalyzed Direct Synthesis of Phosphole Derivatives from Triarylphosphines through Cleavage of Carbon–Hydrogen and Carbon–Phosphorus Bonds

Cited by 148 publications

References 60 publications

Calix[4]arene-fused phospholes

Calix[4]arene-fused phospholes

Pd‐Catalyzed Synthesis of Other Heteroatom‐Containing Heterocycles

Conversion of 2‐Iodobiaryls into 2,2′‐Diiodobiaryls via Oxidation‐Iodination Sequences: A Versatile Route to Ladder‐Type Heterofluorenes

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